- My name's Emeke, what's yours?
- Winston.
- Ask him if he's had A ménage à trois.
- Have, oh!
- Go on, ask.
- Oh my god.
(ethereal music)
- I'm Winston, I'm a vet student.
- I've never been on a real sit down date.
I've been single for,
I think like almost four years now.
- I would trust a grandma with my life
so, I will trust them with my love life.
- Is there a reason why you keep your hat on like that?
- Well first of all, hello Grandmas.
- Okay.
You can call me Nana Paula.
- I'm Lou.
- and I'm Kenny.
- Okay.
Well, are you guys ready to help me land a date?
- You need to take off the hat.
- Okay, I have really bad bedhead.
- Actually, I think he looks good in the hat.
- Let's see how bad you look with your hair.
- Oh boy.
- Oh, that's a bad hair day?
Give me a break.
You ought to be a damn model.
Now take it off, take it off.
Let the guy see you without that.
- Okay, we're gonna bring your first date.
(ethereal music)
- Well somebody say hello.
- Hi, I'm Devin.
- I'm Winston.
- Nice to meet you.
- What do you do for a living?
- I manage a series of restaurants.
- Ask him when his last serious relationship was.
- Ooh, okay.
Have you ever had like a long term relationship?
- I have.
- Can you hear me Winston?
- Yes Grandmas, I can hear you.
Sorry, there's like voices in my head right now.
- Can you hear me?
- I can hear you.
- I would like for you to be funny and say.
Wow, how many exes did you say you have?
- Wow, how many exes did you say you had?
- Like three or four.
- And that's totally normal.
- He needs to loosen up.
- Loosen up Winston.
He looks too stiff.
- I think that's something that comes as you get older.
- Ask him if he finds you attractive.
- Do his parents know that he's gay?
- Do you think he'd take us out to dinner
at one of his restaurants?
- Okay, I've got three rapid fire questions.
- Okay.
- Do you find me attractive?
- Yeah, you're a cute guy.
- Do your parents know you're gay?
- Very much so.
- Okay.
And would you take three grandmas out to dinner
at one of your restaurants?
- Whose grandma's are they?
- I have no idea.
- Give a thumbs up if you're attracted to him.
- Oh yeah, we thought so.
- Don't worry abut that, I don't know what that was.
(laughs)
- How long do you think you'd date him
before you'd want to go to bed with him?
- It just makes sense that you kind of have to...
- He's trying so hard to keep a straight face.
- He's trying not to laugh.
- It's a partner...
- Make sure he wears his galoshes
If you're gonna go back to his apartment.
In other words, glove up buddy.
- How long before you'd bed him down.
- I am being asked how long I would date you
before having sexual intercourse.
And I think I'm being told to wear a condom.
- Very bright.
(laughs)
- Are you supposed to answer that?
- I think in general,
I would like to go on a few dates with somebody.
It's a lot, like to give somebody that.
- The date is over, wrap it up.
- I've enjoyed this date.
- You'd like to talk to him some more,
to get to know more.
- I would like to get to know you more.
(laughs)
- Uh, did that sound weird?
- Take your hat off
and show him what beautiful hair you have.
- It was nice meeting you.
- It was nice to meet you too.
- Take off that damn hat.
- Bye, Devin
- Bye
- You did really well.
How do you feel about it?
- I'm sweating a little bit.
- Did you like him?
- I think so.
- He needs to lose that hat.
- Well, he likes the hat.
- You gotta let it go.
- Maybe that's why sometimes he doesn't find dates
is he's wearing a baseball cap
and they don't take him like.
Oh, he's just another B-ball player.
- He's got to be comfortable.
- Are you ready?
- You can do this.
- You look good, you look calm.
(ethereal music)
- Hi there.
- What hunk of burning love.
- My name's Emeke, what's yours?
- Winston.
- Oh, I like that.
Like it just feels like very classy.
- But it also is very much a pet name.
So most people informed me that one of their relatives,
like owns an old dog named Winston.
- Oh, you're charming him right off the bat.
- Physical touch is like one of my top two love languages.
- Oh, you know love languages?
- Of course, of course.
- I totally buy into that stuff.
I would say my receiving love languages,
words of affirmation.
I like to be told that I'm a good boy, so to speak.
Not sexually.
- Do you remember his name?
- Yes, Emeke right?
- Find out how you spell his name?
- How do you spell that?
- Uh, E M E K E.
- Okay.
- What does that mean? His name.
- How would he show you his love language?
- How would you show me love?
That's a lot to ask on a first date.
- Very easy way for me to show love
is like, through dancing.
- Ask him if he twerks.
- I will not ask that question.
- Ask him.
Come on, does he twerk?
Come on.
- Sorry, voices in my head.
- Could I get thumbs up if you like what you're seeing
and what you're hearing?
- Oh! See, two thumbs.
See.
- Mention his smile, it's very electrifying.
- Your smile is electrifying.
- Is that how you really feel?
- Yeah, yeah.
Is it weird going on a date with four people,
three of whom are adult women.
- Kind of like not fair, like you get backup.
- Ask him if he's had ménage à trois.
- Have, oh!
- Go on, ask.
- Oh my god.
Somebody wants to know
if you've ever had a threesome before.
- Yes, several.
- Oh.
- Jesus.
- Have you ever had one?
- No, but I wouldn't say no.
- You better wear galoshes.
- Are you somebody who's like monogamous?
- Um, I'm Polyamory.
- Oh hell no.
Bye-bye.
- I think a lot of people like conflate it
with like wanting to be sexually promiscuous
But I think polyamory is really about
like the freedom to
build the kind of relationship you want
with the people you choose.
- Give me a thumbs up if you're ready
for this kind of relationship.
- That's not a question of how the date is going.
- He's getting polyamorous mixed up
with just a regular threesome.
- I don't think so.
- Polyamorous is just, you know.
Getting with anybody, a man or woman.
- That's a threesome.
That's a threesome
- No, no. You meet strangers.
I have friends who do this,
they meet up in hotel rooms.
- What exactly are you looking for?
- They, they.
oh god.
- What do you think you're looking for in a relationship?
- I mean, a human to touch me.
- Now he wants a whole bunch of humans to touch him.
- He looks distressed.
- I feel like you're opening like my eyes to polyamory but.
- I just thought you wanted
to just have a relationship,
not go into a full blown orgy situation.
I mean.
- Who knows.
- You better go to Costco
and buy a pack of those galoshes.
- There is a fear like, if I were to get jealous.
- And like jealousy still happens
in polyamorous relationships.
You just have to figure out like,
what is it inside you that you have to deal with?
- I like how he's explaining this.
- I want to ask, would you go on another day with me?
- Yes, I would.
- I thought he wanted a monogamous, straight.
- Yeah, but he wants to know.
- Would you?
With me?
- I would love to go on another date with you.
- It was nice to meet you.
- It was nice to meet you too.
- So what'd you think of him?
- Enchanting.
- The multiple partners kind of threw me there.
(laughs)
- Me too.
- What are you feeling now?
- A little more confident.
I feel like the jitters have gone.
- If you were sitting in the other seat,
how would you want it to go?
- Probably leave the heavy topics for the second date
but you know, maybe it's good to get them out of the way
on the first date so you're not wasting your time.
- Absolutely.
You never get a second chance to make a first impression.
So I say just let all the balls out on the table now.
- Okay.
- Let's go.
(ethereal music)
- Oh shit, another hat.
God damn it.
Take those god damn hats off, buddy.
- Hi.
- What's your name?
- I'm Ryan.
- I'm Winston.
Nice to meet you even though this is some very strange,
like pretenses to meet somebody.
- Yes it is.
- How old is he?
- How old are you?
- I'm 36.
- I'm 25.
- 10 years older than you.
- But I have done things with people
over the age of 30 before, so.
- Okay, okay.
- What do you do for work?
- I worked for the railroad.
I'm actually a conductor.
- Oh, I like.
Toot toot!
- I have never been on a train and it's on my bucket list.
- Well, maybe we can have another date on the train.
- Fun, yes.
Let's go.
- I've got a neck pillow ready to go.
(laughs)
- What does he really do for the train?
Does he drive the train?
- What do you really do for the train?
Do you drive it?
- No, so I'm basically that guy on the platform
yelling, all aboard!
- That's kind of hot.
- You think that's hot?
- Really hot.
(laughs)
- Ask him if he meets a lot of people on his job.
- Do you meet a lot of people on your job?
- I meet a lot of people.
- Have you ever like,
- hooked up, go on.
- Hooked up.
- No I have never hooked up on the train before.
- I've never done it on a train either.
- I'm getting sexual history from grandmas right now
that I don't need to know.
(laughs)
- Drink your water, drink your water.
- I like him.
- I like him too.
We need to have him take off his hat.
- They really like you, but they don't like our hats.
- He has to take his off just for a second.
- Oh my God.
- Beautiful.
- Thumbs up.
- He's sexy.
- How long would you dating before you'd have sex with him?
Condoms have an expiration date.
- Condoms have an expiration date,
how soon do you have sex with somebody?
- Well, maybe a couple of weeks.
- You're not like a first date hookup kind of person?
- No.
- Me neither.
- Ask him if he has been married.
- Have you been married before?
- As a matter of fact, I have been married.
- How did they know that?
- Grandmas are good.
- Oh my god
- I've been divorced for just over a year now.
- Okay.
- What would he do differently?
- Is there something you think you'd do differently?
- No.
- Okay.
- But if he's not gonna change anything from the past,
wouldn't the problem exist?
- I don't know.
- That led to the divorce.
- That's just a lot to talk about on a first date.
- Go ahead, do it.
- Okay.
If you weren't to change anything,
does that mean like the same fate would come?
- It's just because of the type of work that I do.
So I guess I would choose someone differently
who could handle with me traveling as much as I do
for work.
- Ah, I see.
Maybe this is too big of a topic for a first date
but some of the advice I got from my three friends was like.
You have one chance to like, kind of make a first impression
and see if you're compatible.
So, do you want kids
or are kids something that you see in your future?
Would you date somebody that wasn't sure?
- Um, I don't think that I would
just because I wouldn't want to waste that time.
- Right.
- Oh, okay.
- Alrighty, nice to meet you sir.
- Okay.
- That's really awkward.
- How'd you feel about that date?
- I think maybe we realized
that there were a lot of differences
and I wouldn't want to waste somebody's time.
But he was...
- Stunning to look at.
- I know, right?
- Who would you say is your favorite?
- If I had to pick one.
- You're not polyamorous.
- No, you're right.
- Okay, scratch number two.
Eh.
- But that was my favorite.
- No.
- No, You say no?
- Well, you know.
I disagree 'cause you know.
You're young, you should experience things.
- Polyamorous?
- Well, I'm not gonna have an orgy
I'm just saying I want to get to know him.
- I think you're in the process of
experiencing different things.
- Just listen to your gut.
Whatever you decide, we'll support you.
We'll come to the wedding, we'll bring gifts.
It's all good.
- Thank you.
I would love to have you at my wedding.
- I'll make a veil for your hat.
(chuckles)
- Thank you.
That would be, that would be awesome.
(audience applauds)