- I go for either dad bod or really athletic toned bod.

I don't know, but like when I hug,

I just feel like I can just cuddle

and like dive into their like big stomach and shoulders.

[laughs]

- Definitely want someone that's charismatic.

Someone that's funny,

willing to laugh at everything that I say.

- [Producer] So, low expectations?

- Yes! [laughing]

Absolutely.

- [Producer] Zing!

- Yes. - Got 'em.

- Perfect.

To be honest with you, I have no idea what she was wearing.

I was just so attracted to her hair for some reason,

and I just couldn't stop staring at her face.

- He was wearing full-on blazer and a suit.

It was interesting.

It wasn't too bad, but I was like, hm, okay.

- I'm Leonty, and I'm 32 years old.

- I'm Ash and I'm 27.

I'm a model.

- I'm an event manager

at one of the biggest arenas in the world.

Eight months now.

- About a year now.

- Too busy and I need to put myself out there more.

- I think mostly because I'm busy.

I put a lot of time into myself.

Ash, is she fire?

She's lit!

- Leonty, interesting. [laughs]

- Typically, athletic ones, outgoing.

You know, someone who just likes to have a good time.

- I go for a person who's kind, well-rounded personality,

and in general is just positive.

- Funny. - Funny.

I have to be with someone who's funny and intelligent.

- I think for the first five minutes,

I would definitely be nervous,

but I think once we start to gettin' to know each other,

you know, I'll bust out my humor and my wittiness.

- I'm very outgoing, I like to ask questions

to the point sometimes I like to ask questions

that will kinda shake them up.

- I hope she laughs at all of my jokes.

- I hope that he makes me laugh.

I think I'm gonna wear this.

- I'll probably rock this.

I think this looks good for a first date.

That is a great question, I don't really get into the zone.

I just make it happen.

- Can I be honest?

I just chug a glass of wine.

Yes, a little bit.

- Yeah, I'm nervous.

Date number two, date number three,

then I'll take her to my parents' house.

- Potentially a second date.

If not, friendship.

- I don't have any horror stories.

And I hope tonight is not the one.

- I have so many, but I think one of the worst

was when this guy, as soon as we met,

he started lecturing me about his politics,

like are you pro-life, pro-abortion?

And if you are not, you need to do this, blah blah blah,

and I escaped.

I actually haven't heard anyone in my life.

- German soccer player Mario Gutze.

Emmanuelle Chiriqui.

- Ron Swanson, Nick Offerman.

- I'm Pisces, no idea what that means.

- Capricorn.

Super type A, plans, organized,

if I want something, I get it.

- I've had two major relationships in my life.

One was in North Carolina, we dated for about a year.

And then just recently I broke up with someone

eight months ago here in New York City,

where we lived together for about six months.

- I probably about four serious relationships.

Each one lasting one to two years.

They will probably say that I'm a "giving tree,"

like the book.

- Definitely more on the giving side.

I just wanna make them, you know, happy at all times.

- No.

- Never.

- I hope not. - I hope not.

- [laughs] I don't think so.

I have.

- No.

- No.

- Yes.

- Probably wanting to go on many more dates,

having that feeling at the end of the night.

- We just make a great connection.

- Me wanting to go home as soon as we sit down.

- Well, I am in New York City

and I've watched "Men in Black,"

so hopefully she's not an alien.

I'm a perfectionist, so I don't think there has been any.

- I have trouble getting on bar stools

'cause I'm really short, and one time,

I just slipped and fell face flat on the floor.

- I would probably say someone who's just

always talking about how negative someone or their life is.

- If they're rude to the waiter or a bartender, red flag.

I think I gaze into their eyes and maybe like

play with my hair a little bit.

This is not sexy right now, but yeah.

- Probably taking my shirt off.

- Be smart, intelligent, good voice.

- I would say laughing all of my jokes.

And smiling, lots of smiling.

Strangely, I love hair.

Long hair.

- Their eyes.

- Beach.

- Mountains.

- Time. - Time.

- Morning person.

- Night owl.

- Active date. - Active date.

- Leather.

- Leather, but not real leather.

- iPhone.

- iPhone.

No. - Mm, yes.

- Chocolate.

- Both.

I don't like eggs.

- Scrambled.

Neither.

- SpongeBob?

I hope she's breathtaken.

- I kind of really hope he's tall

and funny and smart, maybe a deep voice.

And good fashion sense, I'm asking for a lot,

but just clean.

- Hi Ash, I'm Leonty.

Definitely lookin' forward to this date, a little nervous.

- Hi, I'm very excited and nervous to meet you.

I hope we have a good time and I hope you're clean

and you like eating.

[thumping bassline]

- Just arrived to Brooklyn.

Walkin' over to the restaurant

where I'm going to meet my first date.

Wish me luck.

- So, I'm a couple blocks away from the restaurant

that I'm supposed to meet Leonty at.

And apparently he's already there.

Early, that's a plus.

I'm a little nervous, but I think I'll be fine.

I'm more excited.

[upbeat guitar music]

- [Producer] How you feelin'?

- Great.

- I'm good.

- So we went to a restaurant, I met her in front.

And we kinda had a nice little exchange,

but a little awkward hug.

Kinda like that one arm hug in the very beginning.

- He got there before the time that we were supposed to meet

and when I got to the place, I texted him,

he came out the restaurant and we hugged

and exchanged our names.

He seemed nice, he had a good smile.

He was wearing full-on suit, blazer.

- Ash was very beautiful, very charming.

Really loved her smile.

- His hair and his eyes 'cause it was very blue

and very blond.

- Definitely her hairstyle.

I love long hair and it was just silky smooth.

- We went to this bar/restaurant in Brooklyn.

They have really good, somewhat pricey food.

- So we went to a restaurant in Brooklyn.

Great foods, great small plates.

- I think he wasn't what I imagined.

A person with more of a weight internally.

- I wasn't really expecting anything.

You know, I just kinda to wanted go with the flow

and just see where it ended.

She reminds me of a little bit of a Lucy Liu.

- He looked like this German soccer player

that I can't really think of a name.

To be honest, no.

- Yes, I can say that.

Yeah, so we met in front of the restaurant.

We did an awkward type of hug, especially on my end,

you know, that one-armed hug when you meet someone

in the very beginning.

- So, we got into the restaurant.

He was being a gentleman, pulling my chair out,

taking my coat.

And we sat down, and we actually had a bit

of a conversation even before ordering the food,

so I was just holding the menu like, oh, cool, cool.

And I had to cut him in the middle of it

and be like, should he order?

- We sat down, we ordered food.

We were actually ordered the same thing,

the rice bowl, very delicious.

And we ordered drinks, just one drinks, that was it.

- I ordered a hot toddy,

and he took a while picking out the beer.

He actually asked our waiter different types of beers

and what is the difference and all that

and he ended up with I think pretty much the most basic one.

[laughing] But it was all good.

- And then we just talked about, you know,

life and philosophies and you know,

just tryin' to stay positive throughout our careers

and where we can take it to that next level.

- And we got into some good conversation,

he was all around very positive.

And then he kept talking and talking. [laughs]

And I was just listening and I think at one point,

I was like, should he head out?

And we got the check and we called it a night.

We pegged it. - Yes.

- About two and a half hours. - About two and a half hours.

- A rice bowl. - A rice bowl.

- Great.

- Amazing.

On point.

- Nonexistent.

Being positive.

- Being positive in life.

No.

- No.

- So I paid for dinner, we left the restaurant

and we walked back to our train stations together.

- So, we walked to the train station together.

He walked me up to my platform,

and he got onto his, which was on the opposite side.

And as a train was coming on my side,

I see someone going like, Ash, Ash!

And I look over, and it was Leonty with the biggest smile,

just calling my name and being like, bye!

And I was like, bye. [laughs]

- We exchanged Snapchats as well as Instagram, social media.

And we actually had a better hug at the very end

and where I used two hands rather than one.

- We hugged, it was more like a, to me, friend hug.

Yes.

- I think so.

I think it was on the 50/50 side.

- Bubbly.

- Elegant.

That initial hug, that very first hug.

I'm an awkward guy, it's cool.

[laughing]

Used to it!

- There are some moments after each conversation,

he was gazing into my eyes and I was just like

looking everywhere but his eyes.

I had a coughing fit in the middle of the dinner

for a brief second, but other than that, not really.

- No, not at all.

I think the conversations were fluid.

- Well, like, he spilled his food, I think, a couple times.

And he like kept mixing two words together.