Dating & New York (2021)

[bunniefuu]

-[dramatic music]
-[projector whirring]

[dramatic music]

♪ Beneath the moon ♪

♪ And starry sky ♪

♪ Heaven writes
A lover's song ♪

♪ Writes a song ♪

♪ A reverie ♪

♪ Of happy dreams ♪

♪ Midnight comes
The nightingale sings along ♪

♪ Melody ♪

♪ With harmony ♪

♪ Makes a lover tune ♪

♪ The night will play ♪

♪ Its serenade to you ♪

♪ Love writes a rhyme ♪

♪ And gentle we find ♪

♪ Magic and beauty begin
Or begun ♪

♪ Dance until morning ♪

♪ Drift along ♪

-♪ Listen ♪
-♪ Listen ♪

♪ And you'll hear a song ♪

[narrator] Once upon a time
in a magical kingdom

known as New York City,

in a city that doesn't sleep,
but sleeps around a lot,

a land of dollar pizza
and crowded subways,

there lived two millennials

cursed with the paradox
of choice.

Like many stories, ours begins
on a phone screen

on the latest dating app
called Meet Cute.

She was Wendy Brinkley, a name
derived from the character

who dated the boy
who never grew up.

Wendy scoured her albums
for a photo

that didn't include necks...

and cautiously accepted
her new destiny.

[alarm ringing]

[narrator]
Then there was Milo Marks

and his unread
text messages.

To Milo, Meet Cute
was just another app

for his dedicated folder.

Milo was a ' "...

?

' ", born-and-raised
New Yorker

who had no shortage of selfies

that he justified as self-love.

The app asked you
a few questions,

then wrote your own
personal love story.

[dramatic music]

Romantically, Milo knew
what he wanted,

as did Wendy, but she was
too afraid to admit it.

They had nothing in common,

except an idealized version
of modern romance.

With their profiles set,

they swiped left,
they swiped right.

But one day,
thanks to some magic
and an algorithm,

they had their Meet Cute.

They met at a cute little spot

in the West Village
called Lylis.

Milo found it
on the Infatuation's list

of best bars where you won't
run into an ex.

-He never came back from London.
-He never came back?

-Never came back.
-Does he still have your nudes,
by any chance?

Um, what, are you afraid of him
leaking your nudes?

-Sorry, that was
a weird question.
-If he ever did,

I have nudes of him
that are not as favorable.

Really?
He has peasant nudes.

-What is your baggage?
-I just don't have any.

-Wow.
-Yeah, I checked my baggage.

-No baggage, no nudes?
-Just got my MacBook
in a tote bag.

-Oh.
-Might get some work done
on this flight.

What does it feel like
to be so perfect?

Basically, what I tell people
is like I'm just like you,
except perfect.

-Wow. Oh, my God.
-[laughs]

Thank you so much
for getting a drink with me.

I don't even know how I made it
through my life

until this moment.

But, no, honestly, I think
whenever I meet someone,

I create this fantasy version
of this person.

And then the more
that we get to know each other,

the more that fantasy
just sort of whittles away,

and then all that's left
is, like, this real person.

And a lot of the time,
I don't like the real person

as much as I like
the fantasy person.

Sounds like you idealize
and then devalue.

It's a very clinical language.

-Spot-on.
-Thank you.

-Um, I'm gonna go
to the bathroom, okay?
-Wait, wait, wait.

Do you actually have to go
or do you just wanna check
your phone?

If you just wanna check
your phone, we could do
a mutual check right now.

-I would love
to just check my phone.
-Okay, okay, me too.

-I could use a hit.
-[keypads clicking]

No notifications.

-Uh, cheers to being single.
-[keypad clicking]

What? Sorry, um...

It's okay.
I like a woman who ignores me.

[both laughing]

[gentle music]

[chuckles]

Only in New York
could you make out

in front of a bunch of garbage
and it's still romantic.

[gentle music continues]

[narrator] They kissed
under the stars.

And after a perfectly crafted
follow-up text from Milo

and an equally witty response
from Wendy,

they would go weeks
before they ever spoke again.

[gentle music]

Three weeks and no signs
of un-ghosting later,

Milo and his friend opted
to drink overpriced cocktails

to celebrate someone
from college's best friend

from high school's birthday.

Did you hear about
this In-N-Out Burger

that they found at a bus stop
in Jamaica, Queens?

How did a cheeseburger
fly , miles?

Yeah, that's fake.
That's a viral stunt.

-That's not real.
-You serious?

[narrator] This is Hank Kadner,
Milo's best and most
put-together friend.

He is a financial analyst
at JP Morgan

who is as savvy
with his spreadsheets as he is
with his dating advice.

-People will do
anything for clout.
-No, it's not fake.

-Whoa.
-It was a pristine
In-N-Out Burger.

Who's that?

-No.
-Yeah.

-Don't.
-That's it.

I'm going to marry that woman.

-You know, you always do this.
-Do what?

You point at a girl
and you say, "I'm gonna
marry her."

So, in the off chance you guys
do get married...

at your wedding.
-...you can say you said that -I don't sound like that.

You look crazy.
Look, this is how you look.

[mocking] "I'm gonna marry her."

-That's not what I sound like.
-That is exactly what
you sound like.

-That's not
what I sound like at all.
-Hi.

Can I help you?

-Um, no--
-That's you.

Why did you point at me?

I was making a point.

My friend here, he likes to--
he does this thing where he--

he points
at the prettiest girl at the bar

and he says,
"I'm gonna marry her."

And in the off chance
that he happens

to actually get married
to that girl,

then he can say it
at the reception

and it can be
like a cute moment.

-He does it
in every bar we go to.
-[woman] Aw.

-So it's kind of--
-Okay.

So you think
I'm the cutest girl at this bar?

I think that--
that's pretty fair to say.

[laughs] Ap spritzes on me.

-Um, go talk to her.
-That'd be weird.

-I'm not just gonna
go talk to her.
-Yeah, go.

-What would I say?
-Oh, are you shy?

[meekly] "Uh, I'm shy.
I'm shy."

That's me being shy.
How annoying is that?

We don't have time for that.
Go talk to that girl!

You said you're gonna marry her.
Now you won't even talk to her?

Here's what you do you.
You go over, say "hi."

-Touch her shoulder
a little bit.
-Okay.

And then lean in,
say something funny.

Maybe say it quietly
so she has to, like, lean in
towards you.

-Okay.
-I had an ex who I thought
I was interesting for years.

Turns out he just spoke
really quiet.

[whispers] That's cool.

All right, I'll leave you to it.

-What's up? Hey.
-Hi.

-How you doing? I'm Milo.
-Hi.

-Olivia.
-Olivia.

-Nice to meet you.
-Nice to meet you.

Where are you from?

-I'm from Texas.
-Oh.

[both] A Southern belle.

-Yeah, there we go.
-You're in the big city.

-[Southern accent]
Thank you, sir.
-Mm, you're welcome, ma'am.

-Oh, my God,
we're doing accents.
-[both chuckle]

Help! [laughs]
No, just kidding.

No, I went to college
with, um, a friend of Lucy's

who's also named Olivia.

-Oh.
-Which is fun.

-[laughing]
-And-- what?

[laughing continues]

Do you dress up
or you're like, "I don't do
costumes."

-[both laugh]
-Um, I don't really... yeah.

-Do costumes?
-I like to wear, like,
a fun hat.

Just like a normal outfit,
fun hat.

-I have a face for hats.
-Oh.

It's so round.
Look how round it is.

Just thought I'd come,
be a little, you know, wingman.

-Oh, a wingman.
-Yeah.

That's fun, interesting.
I like what you did there.

One little wing, yeah.
Other wing holding him up.

Yeah, he has really bad
social anxiety, so...

-Oh, wow.
-...I try to help him out
with that.

-Okay, that's intense.
-Yeah.

-Touch it. Touch it.
-Can I?

-I'm giving you permish.
-[both laugh]

-It's soft, right?
You like that?
-Yeah, it's very soft.

-[sniffing] Okay.
-Oh, wow.

-Get the aromatics.
-Breathe it in.

-Let the wine breathe.
-Wow, look at you go.

-Stop-- look at our friends.
-Look at them over there.

-Mmm, you are dying
to kiss my little mouth.
-Maybe I am.

I don't have a top lip,
but I'm-- I can make it work.

-What do you mean?
-I don't have a really big
top lip.

That might be the best wine
I've ever tasted.

Where did you get this?

Uh, it's my boyfriend's family,
actually--

[echoing] My boyfriend's family.

[distorted]
My boyfriend's...

[normal voice] family
actually owns the vineyard

that this is from,
and it's a rosé white wine.

-What happened?
-Did you get her number, brah?

-No. She actually has
a boyfriend.
-[both] Oh.

-How'd you find that out?
-I think I knew that.

Oh, my-- thanks for telling me.

Cheers for telling me
that she had a boyfriend.

-Drama queen. [laughs]
-Whoa.

-Or king. [laughs]
-Progressive.

I don't wanna put you in a box.

Yeah, drama king,
or drama prince over here.

Okay, stop stealing my thunder.

People should have to wear
these shirts

that say "I'm single."

Uh-huh.

Because then it would help us,

know who's single,
who's not single.

So, you found out
she had a boyfriend,
then you just walked away?

Yeah.

-Serious?
-The conversation was done.

-Hi.
-Oh, my God!

-How are you doin'?
-Liv, how are you, babe?

-I'm good.
-Good to see you.

So you'll never guess
what this guy just did to me.

He walked away because I said
I had a boyfriend.

Uh, yes.
Yes, I did.

[Olivia] Why would you do that?
We were having a conversation.

We can be friends.

I don't know if you guys
have heard

of this word before-- friends.

-Absolutely.
-I've heard of that too.

I think that's
a very normal thing to do

is to make friends.

Theoretically, yes,
we can be friends,

but we're in our s--
I'm sure you have your friends,

I have my friends, I don't
really need more friends.

I sort of need something
a little bit more serious.

You're looking for a girlfriend?

Not like a girlfriend,
girlfriend, but--

Raise your hand if you're
looking for a girlfriend.

[train rumbling]

-[indistinct PA announcement]
-[Milo groans]

[sighs] We missed it.

[groans]

-That girl Jessie was cute.
-Yeah, she was really cute.

-You guys seemed to hit it off.
-Yeah.

-She gave me her number.
-Really?

Are you gonna text her?

-I think I'm gonna call her.
-What?

-Yeah.
-You're joking.

No. What are you doing?

-You're joking. Hang up.
-What?

-[whispers] What are you doing?
-It's her voicemail.

That's worse.
That is so much worse.

Hi, Jessie.
Yeah, this is-- this is Hank.

-Don't hang up, press one.
-We met tonight
at Jessie's party.

-Press one, press one.
-Not Jessie's party.

We met tonight at that party.
You told me to give you a call.

-Erase it.
Pretend it was a butt dial.
-So, here I am.

So let me know
if you'd like to hang out...

-Do not hang up.
-...and get a drink sometime.

-Okay. Bye.
-Press one, then three.

-[Milo laughs]
-What's wrong with you?

-What's wrong with you?
-Let me make a phone call.

You just met
and you just left a voicemail
on this person's phone.

Yeah, I mean business.

-Is that okay?
-No, that's psychotic!

I would not do that, personally.
That's not my ministry.

I wouldn't personally do that,
but go ahead.

[Hank] It's not your ministry?

Who are you, Joel Osteen?

Leaving someone a voicemail--
that's not your ministry?

-[continues indistinctly]
-[mysterious music]

Do you ever feel like New York
is talking to you?

[mysterious music]

No.

[enchanting music]

[narrator] Days later,
in a different part
of Manhattan,

Wendy and Jessie took
New York's most reliable
mode of transportation

and floated the idea of never
having to be an ex again.

-Look into my beautiful
green eyes.
-Okay.

When someone says
they wanna date themself,

there's always an ex, okay?

[narrator] Jessie Katz has been
Wendy's best friend

since they met at Wesleyan
and both got dumped the day
before graduation.

They were bound
by their singlehood and love
of New York.

Sometimes it's us,
sometimes it's them,

but behind
every disappearing person,
there's an ex.

-Trust me.
-No, I hate that.
I don't like exes.

I don't like being an ex,
I don't like talking about exes,
and it stresses me out.

When someone brings up their ex,
they're just tryin' to show you

that they were once
a hot commodity.

-Exactly.
-So I should like them
even more,

because they have
a series of exes.

-Speaking of people you like,
what is going on with--
-[boat horn blares]

[narrator] It was at this point
that the nosy app Meet Cute

reminded Wendy
of her date with Milo

and gave her an idea
of how to never be an ex again.

Meanwhile, bored and alone
on the Upper West Side,

Milo is catching up
on his stories.

Instagram stories.

-[both laughing, chattering]
-[Milo] Wait, is that Jessie?

-[text notification chimes]
-[light hearted music]

[narrator]
Until all of a sudden...

[light hearted music]

[narrator] Unknowing
of what was to come,

Milo met Wendy
at a neutral diner

placed equidistant
along the F train.

[Wendy]
So, what do you think?

[Milo] Nope.

No, I'm not.

I don't think so.

No, because I'm just gonna
fall in love,

I'm gonna get my heart broken,
and then you see

how that could be
very bad for me.

-No.
-You use that word so loosely--
fall in love.

You literally said
you were gonna fall in love

with the girl we saw
with the New Yorker bag.

Okay, but did you see her,
though?

Anyway, where were we?

-We were, uh--
-Oh, my God!

We were acknowledging the fact

that we are both mutually
heartbroken people

who want all the benefits
of a relationship

without the miserable t*rture
of actually being in one.

Wendy, a couple hours ago,

I thought that you were
ghosting me.

I was ready to cut you
out of my life,

forget about you, move,
honestly.

Then you text me
out of nowhere,

"Hey, we need to talk.
It's very important."

All lowercase.

You can understand
how I'm freaking out, right?

I'm like, "She's pregnant.
She's pregnant."

And if you are pregnant,
then I'm ready.

Um, we used,
like, so many condoms,
I wouldn't be worried.

-Thank God you're not pregnant.
-Oh, man, I know, I know.

-Wouldn't that be terrible?
-Whoo! I was freaking out.

-Like, I said I was ready;
I'm not ready.
-Rewinding.

Do you not want consistent sex
without the emotional
attachment?

Okay, no, I do want
consistent sex, I want that,

but I also want
the emotional attachment.

Okay, how about this?

We could be each other's
guides, Milo, right?

Like you guide me, I guide you.

I could teach you
how to not be ghosted.

[laughs]
I look like I get ghosted?

-Yeah.
-Me?

-Mm-hmm.
-No. I ghost.

-I don't get ghosted.
-Oh.

You maybe look like
you could use help

not dating douche bags.

I don't think that men
are as complicated
as you want us to be.

You're playing chess,
we're playing Xbox.

-What?
-You're playing chess,
we're playing Nintendo .

-Who?
-[blows breath]

Boom.

You've never blown a cartridge?
[blows breath]

I'm sitting here,
I'm listening to you,

I'm thinking, and, you know,
you seem like a sweet guy.

You seem like
a really, really nice guy,

but I'm thinking that this is
just maybe a bad idea,

'cause I'm just being selfish,
I'm just being selfish.

I'm projecting my own fears,
and I don't wanna take
advantage of you.

I mean, you're a nice dude
and, you know, it's stupid.

So, we should probably just
sit here, enjoy this meal.

Okay, all right, after some
non-awkward silence--

Ah! You've come to your senses.
I am so glad!

Okay, let's talk terms.

Lucky for you, I come up
with this little gem.

[narrator]
This was Wendy's solution
to any future heartbreaks,

because you can't get dumped
if you were never in a real
relationship, right?

[light-hearted music]

Here's the brass tacks--
basically, we don't get jealous
of each other.

And for every night that I spend
at your place, you spend
two nights at mine.

-How is that fair?
-You live with your parents.

I don't.
I live with my mom and Larry.

And they travel a lot,
so I'm being financially
responsible.

I'm not even gonna consider
signing that

until you add cuddling.

-Add cuddling?
-Yup.

And none
of that on opposite sides
of the bed stuff.

I need, boom, % of the night
together, at least. At least.

Separation, that makes me
think of divorce.

-I don't like it.
-Most marriages
end in divorce anyway.

No deal.

Fine!
Fine, you can have cuddling.

♪ We're gonna cuddle
I'ma be big spoon ♪

♪ Sometimes little spoon
'Cause I like feelin' safe ♪

-♪ What? ♪
-You have a nice voice
and we can sing later.

You have to ad lib.

-♪ What? ♪
-I don't know.

-Okay, go on, go on, go on. Go.
-Okay, one more thing.

-This is very important.
-Mm-hmm.

The words "I love you,"
in that order,

cannot be shared with one party
to the other

unless they are used
in a non-affectionate way.

What does this mean?
Let me explain it to you.

Any example of that exemption
would be

if we were to impersonate
someone

or if we use it in a sarcastic
and/or educational

and/or non-truthful tone.

Does that make sense?

-Okay.
-We shake.

[narrator] And so,
once upon a time,
in New York City,

Milo and Wendy's non-love story
finally began.

-Everything was perfect.
-[car horns honking]

This is going to end
with one of you guys
getting your heart broken.

No, we're not, because
we're being really open

and transparent
about the whole thing.

We're not playing any games.

Okay, but in the entire history
of romance,

whenever two people start
sleeping together, like,
it gets complicated.

That's why we did the contract,
so we know what we can
and cannot do.

We set boundaries, so no one's
heart's getting broken.

Yeah, the contract
that establishes you guys
as friends with benefits?

Oh... [laughs]

This is going to end poorly
for you, my friend.

Look, it's not like
we were friends, you know,

and then we started
sleeping together,

and now we're reverting back
to friendship.

It's like, you know,
we started with sex,

and now we're turning that
into a very beautiful

and respectful friendship
with sex.

Here's where I think
it's gonna go, okay?

Act one, inciting incident--
you sign the contract.

You're laughing, laughing,
laughing, having amazing sex.

Congratulations.
Having the time of your life.

You start to get
some inside jokes.

[laughs] "I'm hilarious."

That's my impression of you
in this fun relationship.

Act two-- fun and games.

You guys start to have
the perks of a relationship

without actually having to deal
with being in a relationship,

because being in a relationship
is famously hell on Earth.

And then act three--
one of you randomly decides

you do actually want to be
in a relationship...

And then, yeah, boom,
movie's done.

I don't believe in traditional
three-act structure.

Not every movie
needs three acts.

Some are just one honeymoon act.

It's kind of risk-free
and there's ultimately--

it's just like me wearing
the pants, which is kinda nice.

But does he know that?

Plus, I think
she's as in love with me

as I am with her,
so it's gonna work out.

And the friends
that I was talking about,

they got back together
and, uh, were confused.

They were confused as to why
they got back together.

And they were like,
"Oh, we don't know

how we got back together
after all this time."

They were apart three years.

They weren't together
for three years.

They get back together, and then
they're asking me like,

"What do you think it was?"
I'm like, "I know what it was.

It was roll-over feelings.

Which is when
you're in a relationship,

you got feelings, you got
the relationship planned,

hoping it's gonna be
a family plan, right?

Then you break up, but then
you get back together

with those same minutes
from that phone

and it's like same phone.

Who this?

Whoo! Amazing!

-I think I'm gonna marry her.
-[Hank] Because she laughed
at your jokes?

[Milo] I don't think her mom
likes me, though.

-[Hank] You met her mom?
-Yeah, accidentally.

-[Hank] How?
-Bloomie's.

What were you doing
at Bloomingdale's?

-I was getting free cologne.
-You're stealing cologne now?

No, you just walk in,

and then you
get your free sample,
and then you go.

-Anyway, I see Wendy's mom.
-Wait, Wendy wasn't there?

No, but I recognize her mom
from her Instagram.

-Cool.
-So, I go over to say hello.

So I walk up to her
and I'm like, "Oh, hello."

And then she's like,
"Uh, who are you?"

I'm like, "Oh, sorry,
sorry, sorry, I'm Milo.

I met Wendy on a dating app
and we're sort of friends now.

You're Wendy's mom, right?"

She's like,
"Yeah, yeah, indeed I am.

I don't know who you are."

She didn't know who I was.

So that either means that A,
Wendy did tell her about me

and she doesn't like me,
so she's trying to neg me

by acting like
she doesn't know who I am

or Wendy didn't tell her,
because she takes me as a joke.

-Wait, do we care
what Wendy's mom thinks?
-Yes.

I mean, I want Wendy to like me,
so I want her mom to like me.

Okay, never underestimate
the will of a girl

to disrespect
her parents' wishes, okay?

Make sure you get my T-zone.

I've been told it's very oily.

Ooh, did I tell you
that I broke up with Katie F?

What? I didn't even know
that you were dating her.

You're already breaking up
with her?

[narrator] Katie F
grew up on the seventh floor

in apartment letter F
in Milo's building.

They rediscovered
each other sexually
after a romantic elevator ride

wherein Milo AirDropped
his phone number to her phone,

by mistake, of course.

-[camera clicks]
-[laughs] That's a good one,
yeah.

Is that gonna make it
to your Instagram?

What?

Is it just gonna make it
to your grid?

'Cause I'm usually
in your story, which is dope,

love that, just hoping that,
you know,

maybe we can make
the next step, go to the grid.

What do you mean?

I've posted you
on Instagram before.

-No, you haven't.
-Yes, I have!

That one time we were in Maine
at that ice cream store,
Scoop Du Jour.

We had mousse vanilla.

I remember you posted
the ice cream cone

and then you tagged me

in the photo
of the ice cream cone.

No, your name was in the photo.

Okay, that's not my face,
though,

that's my Instagram handle.

Well, what do you mean?

People are gonna be like,
"Oh, he made that ice cream
for her."

I didn't. I was there,
took the train up with you.

-Do you not get that?
-Yes.

-You do get that?
-I--

So you know,
but you're just ashamed.

No, it was on my Instagram.
I don't understand the problem.

-We should break up.
-Serious?

Yeah!
I think we should break up.

-Actions speak
louder than captions!
-Please stop yelling at me!

It's really nice,
because I realize
the role that I play

is I'm sort of like this
between-relationship doula
for women.

Am I not present with you
right now?

You're screaming at me
in the middle of the park!

-I'm not screaming at you!
-Yes, you are!

No, I was tryin' to have
a conversation with you!

This is so embarrassing!

So they could go
from, like, one guy,

improve themselves, and then
go on to the next guy.

I'm sort of like a manic pixie
dream boy in that way.

I think we need to just break up
with each other.

-What?
-I think it's over.

You're obsessed with Instagram,
with social media.

I'm not obsessed.

You have a sick obsession with
how people think about you.

What are you talking about?

It's like, "Damn,
you're awesome,

but Wendy, she's uh--
she's the one, you know?"

-Right...
-Or at least I think.

-I don't know.
-Yeah.

[Wendy] So, it's over,

because she wouldn't post
a picture of you two?

Yeah.

I think that she was embarrassed

to have people know
that we were dating.

-Hmm.
-I know.

So I had to break up with her.
Had to do it.

Oh, don't be rude
to my friend Milo.

Oh. Yeah... I don't know.

Over before it started,
on to the next one,

which is the name
of my dating podcast,
by the way.

-The one
you haven't started yet?
-We're looking for guests.

I don't know
if it's about dating yet.

It might just be about life,
but if you wanna come on,

talk about any guys
that you're dating,

that you might really like.

If it is,
can you talk about people
who break up with you,

and then still follow you
on Instagram,

and like all your photos
and your pictures?

Orbiters.
They're orbiting you.

-What do they do?
-They're orbiting, you know,
like...

Oh, my God, you're gonna poke
my eye out!

-Stop, stop.
I get it, I get it.
-Okay, whoa.

All right, but there was
this New York Times article
that I sent you.

I don't read any of the articles
that you send me.

-You never read any of the
articles that I send you?
-Who has time?

-You know what really does
annoy me, though?
-Hmm?

I hate it when someone
posts something

and you can really tell
that they're trying

-to get under your skin,
you know?
-Mm-hmm.

They'll post something
at a place that was special
to the both of you.

And then it's like,
"Oh, who's this new person?

They just invited
some new person."

-Yep.
-And they're
at Shakespeare in the Park

and they're
just having a great time
at Shakespeare in the Park

with some guy probably named
Greg or something,

who works in finance
and is a loser.

That is honestly called
"targeted offensive orbiting,"

and it is a serious problem.

It's like a lighthouse
in the deep, dark sea of emotion

that's tryin' to get the boat
back to the dock.

It's literally someone going,
"Hey, look at me.

I'm recreating this experience
that we had together

with someone else,
and I am happier doing it.

Ha ha ha ha ha."

It's like a foghorn.

-It's...
-[both] Foghorning! Yes!

-Okay, that was good.
-Oh, my God, okay.

-[chatter continues]
-[gentle music]

[Wendy] I need some time.

-I'm almost ready,
I'm almost ready.
-Silence is boring.

Shh, hurry up.
Are you ready?

I'm ready.
What are your thoughts?

I thought that was funny,
but it could be shorter.

I thought it was really long.

But it was funny, though.
It was funny.

Okay, okay.

I am still trying to figure out
what the movie's about.

Does it have to be
about something?

It's about a dude
that turns into a dog.

I'm trying to think
of what the movie's
trying to say,

because that's
just such a basic plot point.

A guy turning into a dog?

It's saying that,
wow, isn't it crazy

when someone turns into a dog?

I feel like
that's what they're saying.

No, art is art because
it lets us feel something.

Here's my gist.

I think it's about parenthood

and how it's difficult
to raise a child,

because we really take advantage
of the little moments

and how we need to savor life
a little bit more.

That's just off the top
of my head.

-I need more time to think.
-That was smart.

-Thank you.
-You're making me a cinephile.

-I know.
-That was good.

What if we were a movie?
What would our movie be?

Oh, my God,
I think it would be like
a slasher horror film

where Denzel Washington
plays you

-and Margot Robbie plays me.
-Okay.

And we both get gutted
and die together.

And then we have to solve
our own murders.

And then we come alive
in different universes

and solve who m*rder*d
each of us.

I like the different universe
aspect of it.

-That's nice.
-Yeah, and then we-- exactly.

And then we, and then we,
and then we.

-Stop, stop, stop!
-And then we--

-Clever, but, no.
-No? No hand holding?

Why? No!
Do you want my social too?

-Yeah, that'd be nice.
-I'll give you all my
credit card numbers.

Honestly, I would love that.
You pay for dinner anyway, so.

-That's true.
-[laughs]

So what about holding hands
makes you uncomfortable?

[narrator]
That's Milo's doorman Cole.

I hear he's a really handsome
and charming guy.

-Well, he's not my boyfriend,
so why would he hold my hand?
-Right.

-Can you guys go on dates
with other people?
-[both] Duh.

-That's the whole point.
-Why not?

Who pays for dinner?

-She does.
-We split it.

-Hmm, no.
-Excuse me?

-[scoffs]
-You do.

I literally have sent you,
like, Venmo requests,

and they're all sitting there,
and I am being a gentle woman

by not reminding you
that they are there.

Okay, I got one more
very, very important question.

[suspenseful music]

[bell rings]

Hang on.

Hi.

Sorry about that.
Uh, who are you here to see?

- F? What's your name?
-Brian.

-Brian, all right.
-Okay, he's also totally lying

-about not telling
people's business.
-Oh, my God.

He was the person
that told me my parents
were having an affair.

-Stop!
-Yeah.

-That's unreal.
-I know.

-I'm sorry!
-It's totally unreal because
I'm just messing with you.

-That didn't really happen.
-Are you kidding?

Sorry about that. [sighs]
Where were we?

Important question.
Ready?

What happens when one of you
catches feelings?

Uh, you mean if one of us
catches feelings?

Yeah, yeah, if.

No, no, I mean when.

It's never if.

It's never, ever if.

It's-- it's always when.

You guys are gonna have
a lot of fun...

but it's never gonna work out.

Take it from me.

[gentle music]

[sighs]

Sweet and salty.

How's that?

Hmm.

How about the Razzle Dazzle?

Does it razzle?

Does it...

[both] Dazzle?

All right, that's it.

-No. It's not.
-No. Okay.

Well, at least
you're predictable.

[Wendy] Huh?

Cookie dough.

Why would you say that?

Well, you just gotta
pick a flavor

and then just go
with that flavor.

And why would I pick a flavor
and just go with that flavor

when I can try all the flavors?

Because if you try
all the flavors,

then you never really get
to experience

just one good flavor at once.

-[Wendy] Let me
think about that.
-Mm-hmm, yeah.

Yeah, I think I'm just gonna
exercise my right

-to try all the flavors
because I can.
-Okay.

And I'm going to get
the vanilla cone.

-[Wendy] Boring. Predictable.
-That's not boring.

No, I like vanilla,
because I'm traveled, I'm wise,

I'm cultured,
I've had the other flavors.

Chocolate varies too much
brand to brand.

-Cotton candy, that's one
of the fun flavors, right?
-Yeah.

You take two bites of that,
too sweet.

Thank you.

-It's melting and everything.
-Cheers.

Okay, well, I guess
you'll never experience the joy

of having a Razzle Dazzle,
salted caramel,

-and cookie dough,
in a cup, please.
-[mouths] Okay.

I guess
you'll never experience the joy
of committing to something.

What are you guys
really talking about?

Just some metaphors.

Yeah, metaphors are great ways
to talk about things

-that you don't actually
wanna talk about.
-Mm-hmm.

Do-- do you wanna check out?

[Cole]
Three avoided "what are we"
conversations later,

Milo wished he was the flavor
that could make Wendy happy.

-I think you make me
a better person.
-[snickers]

I'm literally the same person
you've dated your entire life,

and if you're really
on the quest to look
for the one,

then you really have to stop
looking in the same place.

I think you need to give
yourself more credit.

You don't make me
a better person.

That's why this works so well.

We're like the TV show
you watch every night,

that episode of The Office
that you know line by line.

You just know what to expect.

What's wrong with that?

Okay!

Hook, Hook, Hook.
Wait, wait, wait.

Um, no, I know--
stop, I know who is in Hook.

-Rufio.
-Whoa!

-Um, yes, that's his na--
-Has a name.

Okay, calm down.

Uh, his name is, uh...

-[Hank] Three...
-Two...

[Jessie] No, wait,
no, no, no, stop!

-...one.
-Stop! [yells]

[friends shouting, chanting]
Chug, chug, chug, chug!

-Chug it, chug it.
-That's alcohol.

-No more.
-[Milo laughing]

-[Jessie] Oh, Dante Basco, duh.
-Should we split it?

-No, I think we should
do individually.
-Why?

-That's, like,
extremely difficult...
-Hank had two mains.

[Wendy] He did, didn't he?

Yeah, I'm bulking.

You ate like two people.

You got the sea bass
and you got a hanger steak.

But that hanger steak
was not for the table,
that was for you.

Okay, fine, I'll--
I will pay the tip.

-Okay.
-Okay.

-Aw! You guys!
-[Milo] Settled. That's fair.

Say "Thank you, Daddy" on three.
One, two, three.

-Thank you, Daddy.
-[Jessie] Very good.

-Why didn't you say it?
-'Cause it's uncomfortable.

-I always tell them that.
-He liked that too much.

Now that that's settled,
Wendy has big news,
speaking of news.

-Oh, does she?
-Wendy is moving to LA.

She's movin' to LA.
She just told me.

-That's exciting,
that's awesome.
-[Wendy] No...

-I-- what?
-I'm-- I'm just...

contemplating a life there...

Like, on purpose?

Hate that for you.

-LA is a haunted house...
-Oh, my God.

...full of cardboard
sunshine people.

Why did you do that?
See, you've made her mad.

-You're being a child.
-I'm not being a child.

-You're being a child.
-Mm-mm.

You look like a child right now.

The way you're drinking
is childlike.

If they're not a couple,
they're definitely fighting
like a couple.

-Well, they are.
-I don't think--
that was bickering.

-I don't think
that was fighting.
-It wasn't fighting.

You were being kind of dramatic.
That wasn't fighting.

That was a discussion.
We were discussing.

It was-- it was a salon.

Oh, uh, my ex just moved to LA.

-[Wendy] Oh, really?
-I'll give you her number.

-You guys would
totally get along.
-[Wendy] Yeah.

Oh, amazing. [laughs]

That sounds incredible.
What's up with your ex?

Cool.

[Hank] She just moved there
a few months ago.

I didn't know
you still talked to her.

-[laughs]
-I don't, really.

She just told me that
she was leaving to New York.

She told you?
Like, you guys text?

Not often, but she texted me
because we have...

a "text when a big life event
happens" type of relationship.

She's moving to LA?
What is she, an actress?

-She's moved to LA.
-She's an actress?

-No, she works in PR.
-Is she blonde?

Okay, how tall she?
Look at me in the eyes.

How-- hey!

How tall is she?

You know, that's something--
that we don't do that.

We don't have to do that.
We're immune to stuff like that.

-We are immune.
-We don't have that element
to be worried about it.

We can't even get to the point
where we fight.

-[Jessie] I'm not mad.
-You're overreacting--

-I'm overreacting?
It's called reacting, so.
-You're-- I--

-You know that I hate--
-I've mentioned that--

[Jessie] Overreacting?
Are you serious?

I am going to go.

This was so freaking
cool and fun.

-[laughs] Bye.
-[Wendy] Bye.

-[Jessie] Have an amazing
night, everyone.
-[Wendy] Love you.

-[Jessie] Love you.
-[Wendy] Later.

[Milo] You still have
her number?

Yeah, what am I supp--

Am I not allowed to have
an ex-girlfriend?

[Wendy] You need
a whole new phone now.

I'm gonna go,
um, deal with this.

-[Wendy] Okay.
-[Hank] Okay?

-Are you leaving
without paying?
-Leave a card.

-Definitely leave a card.
-But you got a lobster,
that's not even-- [scoffs]

Even the size,
what do you think?

Is there-- no way.

-No kiss? No kiss?
-No.

PDA is a no-no for us.

-Come on, just give me a kiss.
-It's gross, it's gross.

-I don't wanna do it.
-Look at them.

Are you kidding?

I think
they're overcompensating
for something.

I mean, they were literally
just fighting.

And now they're not.
I don't know.

I think they really love
each other.

And I think that
they've been dating
for, like, two weeks.

[both] Two months!

They don't love each other.
That is the honeymoon stage.

I don't know.

So?

What?
My place, your place?

What are we doing, hmm?
What are we doin'?

I think I owe you
two sleepovers, so.

Um, actually...

-I do. -You got other plans?

Okay, all right.

So what?
That's a date?

Yeah.
Yeah, I already got a date.

All right.

I have to dip my toes
back in the water.

Come on.

Actually, while I have you,

is this a good text
to send someone

or is it, like,
way too aggressive?

-Really?
-What?

Wendy, no matter
what I tell you,

you're just gonna like the guy
that doesn't like you back.

Hey, emotionally unavailable
people need love, too, so help.

We're more afraid of you
than you are of us.

That's not helpful.

Give me something more.
Elaborate, please.

Huh. You know,
be your charming self,
make small talk,

have an emotional connection,
you know, bite your lip, right?

But you can't text him.
Do not!

Seriously, you have to act
like he died.

Do not text him,
and then, boom, he's yours.

He'll fall in love with you.

Thank you.

But I have to go,
and I'm gonna call you later.

[Milo sighs]

Uh, yeah, thank you
for the drinks.

I mean, I kind of wish
you let me split it,

but, whatever,
it was really nice of you.

Um, so thank you... again.

Yeah, of course, no worries.

Uh, so drinks again next week.

[Cole] This was Mort,

a man Wendy matched with
on Meet Cute.

He lived
only one train stop away
and was a clean ' ".

Rather than seeing a therapist,
Mort co-hosted a podcast

where he interviewed
ex-girlfriends about
what went wrong,

called Let's Catch Up,
available on iTunes
and Spotify.

So, I'll see you again
for drinks next week.

We'll do drinks next week.

No, actually.

What? Why? what?

I mean, you lied.

About?

Come on.

-What?
-Mort.

-Yes?
-Mort, you said you were ' ".

I am essentially ' ".

What-- what are you
talking about?

You're not ' ".

[exhales]
Okay, fine.

I'm like -- I'm like --
I'm like a solid foot.

I'm like a clean -- ' ".

Sure, you know what?
You're right.

If I take off my shoes,
yeah, I'm six foot.

-But shoes back on,
I'm probably like ' ".
-It's okay, honestly.

' " is merely a number.

You don't wanna give
this a chance

'cause I'm slightly smaller
than I said I was?

"Slight" is generous, Mort,
but I appreciate you
keeping yourself up.

Here, come take a seat, let me
explain something to you.

Your optimism is endearing,
honestly, but let's dig deeper.

Why do you feel the need

to exaggerate certain aspects
of your profile?

-I mean, do you not love you?
-I do love me.

Oh, good.
Let's start there.

It's just that dating--
dating can be so hard.

It is.
It can be.

And I go on all these dates
and I finally meet people
that I like,

and then the more I like them,
the less they like me.

Hmm, I know the feeling.
Do you smoke?

-No.
-I don't either.

Listen, Mort, here's the thing.

[sighs] Sometimes things in life
just don't pan out the way
we want them to,

but you have to be able
to get over it and you have to
be okay with that.

[Cole] On a different couch,
in a different part
of Manhattan,

Milo was enjoying
temporary validation

from all the likes
on his most recent selfie.

He was surprised,
but not shocked,

to see that Katie F
liked his photo

despite their theatrical
Central Park breakup.

He quickly scrolled her grid,

and with no evidence
of a significant other,

her percentage of singlehood
was likely high.

[light-hearted music]

[phone rings]

Did you know that Sunday
is the busiest day for people
on dating apps?

I wonder if it's because
of the impending horror
of the work week.

-Actually, I'm sure
that's probably it, yeah.
-[Wendy laughs]

Oh, and January sixth
is the busiest day of the year.

Why is that?

'Cause people want Valentines?

No, I think it's because
people break up

after they go meet
each other's families,

'cause they realize, "I was
just in this relationship

so I wouldn't be
the only single person
at Thanksgiving dinner."

Ooh, and did you know
that you're % more likely
to be swiped right on

if you use the word guacamole
in your profile?

-Guacamole?
-Mm-hmm.

Hmm.

Do you know what men lie about?

Their height?

How did you know that?

Because I'm ' ", not ' ".

Mmm, right.

Yes, I wish I knew that.

[sputters]

Do you wanna come over?

-That's a rule breaker.
-What.

I am sleepy,
and I'm already in bed,

and I'm watching Harry Potter,
and... yeah.

But I can talk to you
until I fall asleep.

-Okay, I'll settle for that.
-Mm-hmm.

[snickers]
Wait, where did you go?

I just, uh, checked Instagram.

-Oh, my God.
-[phone dings]

-Thank--
-But, uh, yeah, yeah,
I have to go.

What?
Wait, what?

Yeah, I gotta--
I gotta go for real.

Whatever, you suck.

-[sighs]
-[knocking on door]

-[Katie] Hi.
-Hey, what's up?

-Hey.
-[phone buzzes]

-Thanks for coming.
-Yeah, for sure.

-Do I...?
-Good, yeah, yeah, yeah.

Um, so, yeah.

Easy time getting here?

[Katie chuckles] Yeah, I mean,
all of six minutes it took me.

-I took the stairs.
-[chuckles] Oh, okay.

-A little cardio, a little workout, that's good.
-Got my steps in.

-Right, right, that's good.
Do you want some wine?
-I would love some wine.

-Yeah, okay.
-Yes, one of those days.

-I've got a nice Flemish red.
-Yep.

[laughs] Okay.

-You like wine?
-Yeah.

Yeah, yeah, yeah.

You know, I indulge,
I would say.

-Um...
-[Katie laughs]

-[phone buzzes]
-[Katie] It's hard not
to miss it, eh?

-[Milo] Right. Cheers.
-[Katie] Cheers.

[Cole]
Despite the contract stating
they could sleep with others,

Milo had a rush
of morning guilt

and Wendy couldn't help
but feel a little bitter.

I guess there's something
you can learn from that.

Like don't be stupid,
don't just immediately have sex
with someone, I guess.

[Cole] But like
any healthy adult relationship,

the two addressed
their emotions head-on.

-[sighs]
-Why are you being moody?

-I'm not. [laughs]
-You're being really moody.

-No, I'm not being moody.
-Oh, my God, let's not
play this game.

Just tell me if you're mad.

If you're mad,
we can talk about it.

I'm not mad, I'm not.
I was just saying.

[Cole] While one relationship
tiptoed around their feelings,

another was about to take
a huge step forward.

Okay, this neighborhood
is very hot, very hot.

Did you notice the Whole Foods
they were building?

-They were opening one
down the street.
-Oh, on th?

-No, the one on rd.
-Uh, how's the landlord?

Oh, completely insane.

You'd be lucky if you
get your security deposit back,

but you have to ignore
all these red flags for...

natural light.

It's a little small,
right, Hanky?

[both] It's New York!

[Hank] Yeah, uh,
can I think about it?

[realtor] Well, not too long,

because this place
is gonna be snapped up.

A place like this
in this hot neighborhood,
very desirable.

Take five seconds.

Five, four, three, two--

-I'll take it!
-[Jessie laughs]

-Good choice.
-Are you serious?

-She's good.
-Okay, let's go.

You're very good at your job.
All right, let's see.

You're gonna definitely have to
move some of this furniture.

It's very sad.
Very, very sad couch over there.

And you're gonna wanna
move that up.

You're gonna have to get rid
of literally everything in here.

This is the saddest couch
in the universe.

That's scientific fact.

The sad Eiffel Tower,
"I'm a girl who studied abroad"
painting,

you'll have to move that.

-Come on. [laughs]
-You mean, um...

You mean,
we're gonna have to move that.

What are you talking about?

-I know that your lease is up.
-Okay.

It's coming up,
and you don't like
living with roommates...

-I don't.
-But what if you live with me
and I was your roommate?

[Jessie laughs]

-Are you askng me
to move in with you?
-Mm.

-In front of our new friend?
-Yeah.

-Are you nervous right now?
-A little bit.

I know, I could tell.
What do you want me to say?

-You think I'm gonna say no?
-I want you to say yes.

-Of course I'll say yes!
-'Cause I like you so much.

I like you!
I like you so much.

-What do you mean? Wait.
-[Jessie] What?

-You-- you like him?
-Yeah.

-You like her?
-Yeah.

-[Jessie] Big-time.
-Do you love her?

-[gasps]
-Do you love him?

The first time I'm gonna say it
in front of--

-He's obsessed with me.
-Yeah, I love you.

-I love you too.
-Oh, so beautiful! [laughs]

We're gonna live
in this little shit-hole
together.

Okay, but first,
you're gonna have to--

first and last month's rent
and my commission.

You know what?
Anything for you.

You're a queen.
Come here.

-You're our girl.
[smooching, laughs]
-[realtor] Oh!

-Oh, that-- that's nice.
-Thank you.

-[vocalizing]
-[laughing]

We live here now!

That's my shitty couch!
[laughing]

...to grab your attention with
its nice, broad green leaves

and its air filtering prowess.

Now give it a little touch.

-Don't-- no, no, not too much.
-Sorry.

Now it might require
a little bit more maintenance

-than the other plants...
-Mm-hmm.

...but as we all know,
nothing good comes easy, right?

Ah, ha! Do you have anything
from the Jurassic era?

-You know what, let me check.
-I'll look too.

-Let me see.
-I'll give it a quick gander.

You guys just do your thing.

I want something that looks like
it came out of a movie.

So you want a fossil?

I would also want
a fossil, but...

Is there a price tag?

-[gasps]
-[dramatic chord]

What's wrong?

-[Wendy] We have to go now.
-Why?

-I wanted to get the plant.
-[Wendy] We have to go now.

Don't forget, don't forget,
don't forget, don't forget.

-Hey, Bradley! [groaning]
-Who is--

Damn, damn... Wendy, Wendy.
Okay, basically, listen, here.

SparkNotes version.

I dated
that guy Bradley over there

and he basically ghosted me
for an unknown reason.

Maybe it could have been
because I texted him
a bunch of times.

I'm not sure, but he's here,
so we're gonna say hi.

-All right.
-We're gonna be fierce.

Be the better version of you.

-Hey!
-Hello!

Uh-oh, uh-oh, uh-oh.

I was blind, but now I see.
[imitates g*nf*re]

-I see you.
-Duh, missed it, missed it.

[imitates machine-g*n fire]
Sorry, that was aggressive.

-Hi, what's up?
-[Milo] Kind of insensitive,
given the climate.

-Okay.
-How are you?

Good. I mean, I don't know,
how is the sun, you know?

How is the sky?
It's grateful and expansive.

-Thank you, Father, up there.
-[Wendy] Thank you.

Thank you for asking me.
How are you?

-I'm amazing. Look, I'm--
-Come here, come here.

-Oh, okay.
-Mm. [sniffs]

Mm, yeah, it is you, it is you.
Sorry, sorry, sorry.

Brad, baby, I found one.

Oh, Erica.

Hey, uh, this is Wendy,
actually.

-Oh, hi.
-Hi.

-[awkward laugh] Hi...
-[Erica] Hey.

She looks just like you.

-Oh, stop, that's so--
-You're so sweet.

This is Milo.
Sorry, this is Milo.

-He's, um... He's my friend.
-Yeah, hey. What's up?

He's my, um, sex friend.

-Yeah, by contract.
-By contract, by contract.

Well, Erica's my fiancée.
[laughs]

So, we're waiting.

[laughs] Just kidding!
We're freaks!

Wow!
Did you hear that, Milo?

He has a fiancée now.

That's crazy!
It's wild!

I just-- I remember
you kind of saying something
along the lines

of, "Hey, you know, Wendy,
I don't wanna date you anymore.

I wanna date myself
and be single."

And I was like, "Oh, cool,
you go do that."

Well, last time you saw me,
I was like... [snorts] "Whoo!"

-You know?
That was me!
-[Wendy] Yes, yes.

But not anymore, not anymore,
'cause I was looking.

I was searching,
I was searching.

But, you know,
the universe provides, right?

"I was trying to date myself,"
you know,

what an egotistical thing
to say.

-No, babe, that was your past.
-That was my past.

Then they put us together
at the singles' table

at a mutual friend's wedding
and, um...

I don't know
how to describe it,
we just fell in love.

We just fell in love.

I'm so happy to say that
out loud.

-[Erica] It still gets me.
Oh, my God.
-Yeah, baby.

Isn't that great?

-Wow.
-We found the energy.

-Isn't that great?
-That's great.

You know what that is?
That's rollover feelings.

It's like rollover minutes,
but with feelings.

Huh.

It's like rollover minutes,
but it's with feelings

and you got the family plan
of feelings.

-Like the phone plan!
-Oh, my God, oh, my God!

-I'm gonna roll over
with laughter from that.
-Yeah, oh, my God!

You jokester.
So charming.
He's funny.

You're very funny.
What does he do?

-It's a new bit I'm working on.
-He's a comedian.

-Oh, I love Canadians.
-Me too.

[Bradley] That's so cool.
They are very funny.

I have some rollover feelings
about a coffee table there.

-Yeah. Oh, my God!
-I'm sorry, I stole your joke.

-Mee-lo?
-Milo.

-Milo, great. Okay.
-Milo.

-[Bradley] Bless you.
-Yeah.

Uh, good luck with the sex.
It sounds fantastic.

-Bye.
-[laughs] Goodbye.

Blessings to you.

[Cole] After running
into Bradley,

Wendy was visited
by Ghost of Boyfriends Past.

Always the heartbroken
and never the heartbreaker,

it finally clicked.

To never feel heartbreak again,
she need only do one thing.

On a different phone screen,
with no new matches,

Milo made
a life-changing decision.

[light-hearted music]

[Cole] As both were down
on dating,

Milo and Wendy visited
Tompkins Square Park,

New York's breakup hot spot,
to relieve some despair

via people who were full
of even more resentment
than they were.

[Milo] "You don't take
my food blogging seriously."

[Wendy] "I would love to take
your food blogging seriously,

but you
literally only blog things
I'm allergic to, I can't eat."

[crying] "Uh, yeah, I blog
things that you're allergic to

because I wanna raise awareness
around your allergy."

-"Oh, babe,
I need you to stop crying."
-"I'm not crying."

-"You're always crying."
-"I don't always cry."

"Can we just have
an adult conversation
for once?"

"We're are having
an adult conversation."

-"Oh, my God."
-"Stop. Stop it."

"I literally can't.
I need to go have a beer."

-"You're just not emotionally
vulnerable like I am."
-"I am!"

"And that's something
that you need to work on."

"I bought the journal
like you told me to."

-"I bought it!"
-"You never use it,
'cause I've read it."

You ever think
about how now it's so easy
to break up with someone?

Back in the day, what?

You had to, like, show up
to their house, do it in person.

Now you can just...
"It's not workin' out,
slanty face."

I, for such an occasion,
have a pre-written breakup text.

-Like a template?
-Yeah.

-Seriously?
-Yeah.

-Show me.
-No.

Why?

Fine.

-You ready?
-Lay it on me, yes.

-Break up with me,
break my heart.
-Okay.

[clears throat]

"Hey, insert name there,

thank you so much
for the last couple of dates.

They were really fun.

Unfortunately, I feel
more of a friend vibe going,

but you're such a great person,
and I really hope

that you have a great future
and a successful year."

-That's it?
-That's it.

You feel more
of a friend vibe going?

If I got that after a date,
I'd be like,

"Oh, great,
they wanna see me again."

-What?
-Yeah, that doesn't seem bad.

I think you're the only person
that would read that text
that way.

Honestly, just ghost me.

I'm not even... [laughs]
I don't wanna even get the text.

Just let me spiral,
let me make up my own story.

-Let me write that
in my Noteshelf.
-Okay, I keep it in mine.

"Ghost Milo."

It's just every time
I've liked someone,
they've ghosted me.

And at this point, fine,
I'll just be single forever.

-Are you kidding?
-It's like, what am I--
what am I doing?

You are smart, and funny,
and kind, and inspiring,

and hard-working,
and determined, and passionate.

You're gonna be just fine.

Okay.

-That was a good pep talk.
-Thank you.

I think I know what I want now.

What is that?

"I think I'm gonna be
a food blogger and..."

"You're gonna be
a food blogger?"

"I'm gonna start by blogging
about this brunch
we're going to."

-"I'm all about brunch."
-"It's gonna be so good."

"It's gonna be so good, right?
It's gonna be so good."

-"You want a ride?"
-"Okay, go."

To blogging!

-[Milo] Oh, my God.
-[Wendy] Your curls are
literally perfect today.

-Can I touch one?
-Yes, every curl has a story.

Does it?
Tell me this one's story.

What happened to this one?

-He is a first-generation
college student.
-Mm-hmm.

And he is going to be
taking care of his family.

-Oh, sad.
-Which is so--
But he really takes pride in it.

He really takes pride
and enjoys it.

-Get another one.
-All right, I want this one.

-[Milo] That one
is a billionaire, actually.
-Okay.

-[Milo]
All the other curls hate him.
-[Wendy] That makes sense.

-That's makes sense.
-Yeah.

[Wendy]
Like the Daddy Warbucks.

I don't know why I'm referencing
musicals today.

What's going on here?

-What?
-What?

You decided to sit
on the same side of the booth.

It's kind of a pretty big booth.

Uh, would-- yeah, well,
if we sat right there,

we'd be closing ourselves off
from the world.

Exactly, I like to look.
Like, "Oh, hey, what's up?"

Oh, look, that guy--
that's a great coat.

-Maybe I wanna get that coat.
-Wow.

-Oh, a taxi!
-Oh, look, there's a taxi.

We're taking in New York.

Also, the seat creases there.
I don't wanna sit in the sink.

If you don't like the streets,
don't live in New York.

Also, I like to look at you
in the eye.

I like to have a conversation
with you eye to eye.

Are you gonna pull up a chair
right there and then--

[Wendy] Exactly!
Exactly, that's so rude.

-[Milo] It only makes sense.
-Something's different.

You guys
are more into each other
than you were before.

-That-- I mean, yeah.
-[laughs] No.

[Wendy] It's, uh...

You've noticed
that we have a...

-Have a freelance.
-We upgraded.

We're freelancing
an upgraded relationship.

[Milo] Yeah,
a freelance relationship.

Oh, a free--
a freelance relationship?

Funny you should ask because...

Because a freelance
relationship is, uh...

a relationship where you are...

[Wendy] Given your status,
you have a fair amount
of benefits.

You have a certain amount
of relationship benefits.

Benefits that you can take,
and you leave the awful ones.

So it's friends
without benefits.

Depending on your employer
and your insurance package.

-Boom.
-It's a bit I'm working on.

-You got yours wallet-size?
-I did, actually.

-It's really nice.
Here, I made you one too.
-Oh, thank you.

Let me see this.

And look, laminated.

You went to Staples,

and took a little piece
of paper,

and made them laminate it?

-Why are you so invested?
-What is this? Do you litigate?

Okay, can you guys stop talking?

I called you here today
because, um...

[dramatic music]

[Wendy gasps]

Yes!

Yes!

[gasps] Yes, put it on,
put it on!

-Okay, seriously,
though, that is--
-That is--

[both] Amazing!

Yeah, I'm gonna ask her
on Thanksgiving.

-Wow.
-You wanna touch the box?

-Yeah, it's velvet.
-This whole relationship

is moving
at seventh grade speeds.

-Yeah, we're doing...
-It is, kind of.

[TV playing in background]

[Milo] Is it messed up if...

Huh, okay.

Do I owe this girl--
woman a breakup text

if we only went on one date?

[Wendy] No.

Maybe, honestly,
if you had sex with her.

-Did you have sex with her?
-No.

Well, then you don't
really need to explain anything.

It's not really ghosting
if there's no sex involved

or if you went
on more than one date.

Okay, I lied.
We had sex, we had sex.

Then you should probably
send a text.

You should send,
like, a simple breakup text.

But I feel like if I do that,
then she's gonna think

that it's because we had sex,
but it's not.

It's because...
I just didn't like her.

Oh.

She just...

I feel like that sounds harsh,
but she...

It does. [laughs]

She just wasn't it.
She just, she just wasn't it.

She kept asking
what time I was born,
and that was the only question

she asked about
my personal life at all.

The whole date.
And then at the end
of the night,

she was like,
"Have a wonderful night,"

just like in this weird tone,
like Mary Poppins tone.
[chuckles]

-Mm-hmm.
-And she lives
in Murray Hill, so.

-Oh, very dramatic.
-That is a no.

Well, why don't you just
be like,

"Hey, you know, date was fine,

we're better as friends"?
[chuckles]

I don't wanna see her again.
[chuckles] I don't wanna
see her again.

Okay, then just be like,
"Hey, I'm not looking for
anything serious."

Well, that'd be lying.

Okay, then just don't say
anything at all.

Okay, settled.
I won't say anything.

-Boom. Nailed it.
-Easy.

Boom.

Could you pass me
a fortune cookie?

No, it is bad luck to eat
a fortune cookie

before you have finished
your meal.

-Okay. That makes sense.
-You're welcome.

Just gonna... [clicks tongue]
get some dinner running.

-[scoffs] God. So smooth.
-[chuckles]

-What if we became boyfriend
and girlfriend?
-[chuckles]

Yeah, what if we were boyfriend
and girlfriend?

-No, I'm serious.
-It's a great idea.

What if we were exclusive?

But you don't want that.

Yeah, I do.

Wait, why are-- why are you
doing this?

Because I think that we would
be good together?

Mm-hmm.

And I like what we're doing.

You know, we're-- we're--
we have this great thing where

we're allowed to be single
but not be lonely.

-Like, that's the dream.
-Oh, I don't know.

I feel like we have two
different versions

of what a dream is.

Okay, well,
then maybe we should stop.

Stop what?

Stop hanging out, stop talking
every day,

stop watching TV shows together.

Okay.

That's cool, but the thing is...

I love you.

-[laughs]
-I love you.

[chuckles] I'm sorry.

You don't love me.

There's no way,
you don't love me!

How could you love me?

What do you mean
how could I love you?

What-- we spend so much time
together.

-Milo, Milo, Milo, Milo, Milo,
you love everyone.
-We're always--

You love everyone
and everything.

You're afraid.

-You're afraid.
-Excuse me?

-You're afraid.
-What are you even
talking about?

-You're afraid to be loved.
-That's not fair.
I'm not afraid.

You...

So if it's
going good, you like it,
you're having a good time,

which is what you said,
we're havin' a good time,
what's stopping you?

Okay, okay,
you wanna know what happens?
What happens when we date?

Let's just say we start dating,
all right?

And then suddenly, there are
all these expectations

and they just keep piling,
and piling,

and piling, and piling,
and piling,

and then suddenly, you know,
I'm getting mad at you,

because, you know, you're not,
you're not expressing your
feelings well enough

or you don't even wanna come
near me,

because I'm suffocating you
all the time.

And then we finally
get to the point
where we break up,

and we never see each other
again,

and we have no friends,
and we're just alone.

That wouldn't happen. [chuckles]

That wouldn't happen.

Not to us.

You're afraid of being alone.

I'm not afraid of being alone.

I love bein' alone.

I've been alone so much.

I just wanna be alone with you.

And I wanna be alone alone.

[dramatic music]

[inaudible dialogue]

-[birds chirping]
-[indistinct chatter]

-[notification dings]
-I haven't even thought about
her in what? Uh, three weeks.

-I can't even-- it-- it's so far
out of mind at this point.
-That's great!

-[notification dings]
-[sighs] I can't get Milo
out of my head.

Mm, I'm sorry, it'll pass.
Remember, half the time
you were together

equals the time it takes
to get over them.

It's math.
I'm basically a scientist.

We were supposed to be
the unsinkable relationship,
you know?

-Like the Titanic.
-The Titanic sunk, dude.

But the love lasts forever.

I'm worried I made a mistake.

No, it didn't work out,
that's okay.

Just 'cause it ends doesn't mean
it wasn't a successful thing
when it was happening.

-You know what I mean?
-Yeah, but what if I didn't
give it a real shot?

-I always do this to myself.
-Is this self-sabotage?

I mean, I really just hope
that she found somebody
that she likes.

Like, I'm good, I just hope
she's good.

What? Why are you wishing--
look, look,

you are being way too hard
on yourself, okay?

You guys weren't supposed to be
"not together" together anyways.

I mean, how can you even
break up when--

-You weren't even dating.
-[sighs] It's for the best.

I'm sure he'll just fall
in love with the next girl

he locks eyes with
on the L train.

-Have you spoken to each other?
-Have you spoken to her?

-No.
-I accidentally viewed
her LinkedIn.

Well, he viewed my LinkedIn.

-How is he?
-How is she?

-You'll see her at the wedding.
-You'll see him at the wedding.

-Are you alone?
-Wait, who are you talking to?

-Oh, I'm with Hank.
-I'm with Jess.

-Pi-pa-po.
-That's so cute.

Cute.

[both] Are you seeing anyone?

I'm just sort of, like,
dating myself right now.

Yeah, just-- yeah, and I'm
really happy about it.

Yeah, actually, this guy.

He's in finance,
he works constantly,

and he's completely emotionally
unavailable,

which is perfect,
and I'm really happy.

[both] That's great.

[both] Dating sucks.

-[indistinct phone chatter]
-[man] Uh-huh.

Absolutely.

Well, we can definitely
be there Monday if we have to.

I would never say we won't.

Okay.

Absolutamente.

No, we're delighted.

You kidding me?
This is great!

-So, hey.
-[Cole] This was
Trent Wilkinson,

an incredibly emotionally
unavailable -year-old

who lied about his age
to make the Feingold
Under list

for selling his sock company,
GotSoxx, spelt with two Xs.

He DM'd Wendy on Instagram
after finding her geo tag

at Surf Lodge in Montauk.

Wendy had spent
the last three weekends

at Trent's apartment in Tribeca

and even had
her own toothbrush.

Attention, uh, Kmart shoppers,
I'm gonna be presenting

to, like, a whole bunch
of restaurant groups

because they said that my app
is brilliant.

-Wow! That's amazing!
That's so amazing!
-Yeah! I know.

Oh, my God!
I mean, it is brilliant
and you're brilliant.

-Yeah. Makes sense right?
-Yeah. It does.

-But, yeah.
-It makes perfect sense.
When are you, um, leaving, then?

Uh, it's, like, Sunday.

Sunday night.

Sunday, like tomorrow?

Uh, yeah.

-Tomorrow, uh-- tomorrow night.
-Awesome.

Awesome, and how long are you
gonna be gone?

They said, uh, it was gonna be
like meetings,

and greetings,
and stuff like that

for, like, a couple of weeks.

-Wow!
-Yeah.

-That's amazing!
-Yeah.

No, I know, it just, uh,
maybe we could, like, uh,

just kinda slow her down
a little bit.

Yeah, I-- I know.
I-- yeah, I mean.

Just, like, pull the car over
for a bit.

-Oh.
-Bad metaphor.

Uh, just slow down.

[kissing]

[Cole] While Wendy sold
all her stock in Trent,

Milo was three stops
into the one

on his way to a John Mayer
concert.

Did I tell you about the time
that I got a fortune cookie?

-No fortune
in the fortune cookie.
-No.

Her name was Jenna Brookes,
and she was a recent graduate
of NYU's Gallatin program

where she wrote her thesis on
the life, death, and rebirth

of chivalry in millennial
dating culture.

Yeah, there was no fortune
in the fortune cookie.

-That's crazy, yeah.
-That's crazy.

-[chuckles]
-What's wrong?

-Nothing. No.
-Something's wrong,
what's wrong?

-No, I'm excited.
-No, you're not.

-Yes, I am.
-You're not excited,
something's up.

-No.
-We're going to see John Mayer.

-Yay!
-You don't seem stoked.

-No, I'm excited.
-Something's wrong.

♪ Something is wrong ♪

I'm not going to stop
bothering you

until you tell me what's wrong.

I think-- I think we want
different things.

What?

What, what do you mean?

What are you talking about?

I don't-- I don't think I see
a future with us.

No.

You FaceTimed my mom.

-Yes, that was--
-I let you FaceTime my mom.

Well, she's wonderful.
I loved her!

Oh, I wish that we-- I love her.

[automated voice] The next stop
is Heartbreak Boulevard.

I think you, uh, I like you.

You deserve someone great, so...

No, I'm sorry, I don't wanna
kiss you.

Okay, don't cry.

I have to-- I have to go.

-[Milo] Dang it!
-[Cole chuckles]

Things turn around, they change.

That sounds like it should be
encouraging,

but it's actually really
depressing.

Okay, new topic.

Uh, the podcast thing.
The podcast thing.

Did you-- did you start it?
You should start it.

Yeah.
Yeah, I'm probably gonna
do some, some episodes.

I just gotta get a microphone,

and then come up with some ideas

for episodes and the podcast.

Well, here's an idea.
You should have me on
as a guest.

Maybe not like your first guest
out of the gate,

but let me-- I quit this place,

I'm gonna spill all the tea
on everybody.

I mean, there's some stuff
that's going on in here

that I think the listeners

would wanna know.

-Oh.
-Yeah.

Come on, man,
I miss you smilin'.

You're, like,
one of the few reasons

why I stay in this place.

The phone never stops here--

-[phone rings]
-Front desk.

[Cole]
At a bar in Hell's Kitchen,

where she would never return,

Wendy listened to a man she met
at Whole Foods

talk about his screenplay
that would never get made.

[man] Yeah, so the script's
back at my place

-if you wanna come read it.
-So this is really fun.

Um, I might-- I'm gonna go to
the bathroom first before that.

-Lovely invite, thank you.
-We can go right now.

-I'm actually
right around the corner.
-Um... yeah.

You know, uh,
I could play the lead or,

-or you could play the lead.
-Yep.

-It's sort of a strong
female heroine.
-Yep.

And, you know, we're thinking...

-[dramatic music]
-[gasps]

Hello, hello, hello.

I only got about five,
so let's keep 'em comin'.

[woman ] Hey, hey, yeah, um,
okay, um,

so who paid for dinner?

He did, but I did offer
to split,

and then he insisted
on doing it,

so I was like, "Whatever,
this is terrible anyway."

[man] Will you ever see him
again?

You know, I like to go into
these things open-minded.

You know, if it goes well,
it goes well, but--

[woman ] Look, we all know
dating sucks,

but wouldn't you just rather
be with Milo

than keep this up?

[camera shutters clicking]

Is this an interview or is it
a therapy session?

-Thank you so much, goodnight.
-[reporters clamoring]

[dramatic music]

[message dings]

[message dings]

[message dings]

[keys clicking]

[dramatic music]

[keys clicking]

So, Milo, you just got
your heart broken.

How are you feeling?
What's going through your mind
right now?

Uh, thanks for having me,
I'm really excited to be here.

I am completely dead inside.

I feel nothing.

I feel like a no one, a nobody.

I haven't showered
in a long time. [chuckles]

Wow, that's amazing!

Everybody, give it up
for this guy, he's so good.

So are you wondering why maybe
the breakup happened?

Do you think it's something
that you said

or maybe something
that you didn't say

or are you just totally broken
as a human being?

I'm sort of like a cracked
iPhone screen right now.

Yeah, you could fix me,
but it's probably best to just
upgrade to the next

and better thing. [laughs]

All right, everybody,
that's all the time
that we have.

Give it up again for Milo.

He's so good, he's so funny,
isn't he great?

Isn't he amazing?

Isn't he great?

Isn't he so good?

Milo's so great, he's so good!

Isn't he great?

Isn't he amazing?

Isn't he great?

Isn't he amazing,
isn't he so good?

Such a good catch.

So funny, so good, so funny.

You're strong, you care,
you're a catch, you're humble.

You're-- you're
underappreciated.

You, um... [sighs]
You're trying.

You're trying, you're trying,
you're, um... [sighs]

Ugh, I love New York.

The only place where you can get
toilet paper,

a toothbrush, and a turkey
bacon sandwich

all in one place.

[Milo] This is a decent one,
but I really like a "bougdega"

-instead of just a plain bodega.
-[Hank] Oh, no.

-You know what I'm sayin'?
-This is, this is New York.

-This has everything.
-Yes, I know the rent
is gonna go up,

but the gluten-free pasta
is kind of worth it.

[Hank] Yeah, but I wanna see
a cat.

Oh, planning a wedding
is so stressful!

Come on, man, I don't know
why you're so stressed
about this.

You're getting married
to the love of your life.

Didn't you get
like a wedding planner
or something like that?

No, do you know how much
they cost?

I watch a lot of wedding
videos on YouTube,

I could do it for like .
But I do like a minimal fare
sort of thing.

-Yeah, thank you, thank you.
-Small invite list.

an article
Which is good, because I read We're doing it together!

that said that couples
that plan together
stay together.

What was that, a late daily?

No, it was a meme on Instagram.

How do you know that she's
the one?

Jessie.

Oh, I don't know.

I guess I don't think about it.

I guess we both just don't
overthink it.

Well, what if you're
in a relationship

and you're both like prone

to overthinking things, then?

If you need to get over
this girl,

you need to delete
all the apps, okay?

No Venmo, no Instagram.
No Twitter, none of it.

Because if you don't, you'll be
getting into this space,

which is like this weird
spiral depression

Where you become very annoying
and a hypochondriac.

-Did I tell you
that I found a lump?
-Where'd you find a lump?

-Right there.
-That's your Adam's apple.

That's not what
the internet said.

-So you're gonna reach out?
-No.

That would just make her mad,
so I'm not gonna do it.

I'm just gonna fall back,
give her her space.

-That's it.
-Really?

No grand romantic gesture?

That stuff is the
take-me-back-culture thing.

No, that's toxic,
it's a disease,

and I'm gonna be the cure,

even if that means I never get
to tell her that I love her.

Right, you've told her
that you love her.

Yeah, but I mean tell her
I love her

and mean it, you know?

Like, I love you.

Like, [grunts]
like-- what's that?

-Incense, Jessie loves it.
-[register dings]

She likes bodega incense?

[Cole]
Wendy cherished New York

for its endless encounters
with the people you love

and the places you learn
to love them.

[dramatic music]

[indistinct chatter]

[Cole] Sir.

By now, you've probably
figured out

that I am that soothing,
old voice you've been hearing

holding your hand through
this tale of commitment.

Did I mention that I also
moonlight as a voice-over
artist?

-[woman whispering]
-Hang on.

-Wendy!
-Hey!

-Hi!
-Cole, what are you doing here?

-My job.
-Oh, wow.

What's up?

-You okay?
-Yeah, I'm great.

I'm great, I'm not here
to see Milo. What?

-What?
-Who said that? [chuckles]

No, no, I'm here to--
to go to a meeting.

-I'm here to go to a meeting,
a meeting.
-Oh, here.

No, no, no, no, no,
just in the area.

It's this way. Um... [sighs] It's this way.

-Okay.
-So bye.

-Bye.
-Bye.

I love a good New York
love story.

The city, you know,
it's one of the only places

where you could--

-Hi.
-Hi.

-Um...
-What's up?

Just a quick question.
It's nice.

Um, is Milo, uh, upstairs?

Yeah, nope.

[stammers] I don't think so.

Oh, cool. Cool. Uh...

[stammers] Did he maybe say
when he was gonna be back?

If he's maybe gonna be gone
all night

or just like five more minutes?

-Wendy. [sighs]
-Right.

-I hate to be the one
to tell you this.
-Okay.

I think he's seeing someone.

Okay.

Okay.

I'll see you.

I'll see you, Wendy.

Little did she know that Milo
wasn't seeing anybody

and was, in fact,
painfully single.

And where better to doubt
your own singlehood

than under holy matrimony

at the very bar
in which they met,

where love filled the air--

the wedding of Hank and Jessie.

I'm not sweaty,
it's just really hot.

Okay, I'm nervous, I'm nervous,
I'm nervous.

[Hank] Uh, you're gonna
do great, man.

How are you so calm?

Of course I'm calm.

I'm marrying
the love of my life.

-I'm proud of you, man.
-Thanks.

I'm so proud of you.
I really am.

So what are you gonna say
to her?

-Who?
-Don't "who" me.

I don't know
who you're talking about.

I love you.

-Bring it in.
-Mm. Thanks.

And you are not an ugly
Jon Hamm, I take it back.

You are a hot Jon Hamm.

-[dramatic music]
-[people chattering]

-[gasps]
-[gentle music]

[dramatic music]

Everyone, please take
your seats.

The bride and groom would like
to share their vows

with us tonight
and with each other.

-Jessie.
-Yeah.

The first day that I saw you,
I pointed at you

and said, "I am going to marry
that girl."

-I know.
-[both chuckle]

-Jess, it's my vows.
-Okay, sorry.

-Okay.
-You go.

Mm, no, stop Not yet!
Stop, don't do it yet.

Sorry. [chuckles]

-Start over.
-Okay.

-Mm-hmm.
-First day that happened.

-Yes.
-I was doing it as a joke.

-Uh-huh.
-But you have kept me laughing
ever since.

-Mm-hmm.
-I promise to be
your best friend

and to love you always.
I love you.

I love you.

Hank, a lot of people
say that cheesy thing

where they're like,
"I don't always like you,
but I love you,"

but I like you and I love you.

And I don't even care
that you always fall asleep

the second we pick a movie,

and I don't care that sometimes

you only respond "ha-ha"
to my texts

and don't add additional info.

And I really love that we both
like that meme

about birds that look
like old ladies wearing hats.

And I just love you so much

and I'm the luckiest girl
in the world

that you love me, too.

Is that good?

You like that shit?

[Jessie laughing]

Ooh!

Fashion moment.

-Same time.
-At same time?

-Okay. [laughs]
-One, two, three.

You may now kiss the bride.

-[dramatic music]
-[audience cheering]

All right, let's get drunk.
[chuckles]

♪ Relive that moon ♪

♪ And starry sky ♪

♪ Heaven writes
A lover's song ♪

♪ The reverie of happy dreams ♪

♪ Midnight comes
A nightingale sings along ♪

♪ Melody with harmony ♪

♪ Makes a better tune ♪

♪ The night will play ♪

♪ Its serenade to you ♪

♪ Love writes a rhyme ♪

♪ And chance that we find ♪

♪ Magic and beauty ♪

♪ Begin, ah, begun ♪

♪ Dance until morning
Drifts along ♪

♪ Listen ♪

♪ And you hear the song ♪

[dramatic music]

[Wendy] Do you not want
consistent sex

without the emotional
attachment?

[Milo] I want that,
but I also want

the emotional attachment.

[Wendy] The words "I love you,"

in that order,

cannot be shared

with one party to the other.

[Milo]
You just gotta pick a flavor

and then just go
with that flavor.

[Wendy] I care about you
so much, Milo.

Will I see you again?

-Yeah.
-[dramatic music]

-Hello. Hey, hey, what's up?
-Hi, hi.

-How's it going?
-[both chuckle]

I really miss you.

I really miss you.

And I would really like it
if you were back in my life.

I'd like to be back
in your life, too.

And I promise I'm done trying
other flavors.

I just want one.

I love you so much.

I love you, too.

[dramatic music]

[Cole] Once upon a time,

in a magical kingdom
known as New York City,

there lived a happily married
couple.

Then there was Milo and Wendy
or Wendy and Milo.

Maybe it was vows,
the ubiquitous feeling
of romance,

or the magic of Manhattan,

but they finally had
true love's kiss,

and the heartbroken
learned to love again.

Their thread began again

and they finally dated
happily ever after.

[dramatic music]

For a few more months.

[dramatic music]

[notification dings]

-♪ Two, three, four ♪
-[dramatic music]

[dramatic music]

[dramatic music]