ZACH STEWART: Since I walked up the 11 floors to his apartment that viewed all of Boston Common, I knew I had met my husband.

(audience laughter) JACK SIMON GREY: And I feel the tension in the room skyrocket.

This is either about to be the most awkward experience of my life or the most romantic.

TERRILYNN MOORE SMITH: But I did see this man with snow white beard and sparkling blue eyes, and I thought, "Oh, my goodness, he is handsome."

THERESA OKOKON: Tonight's theme is "Meant to Happen."

There is nothing that enchants us quite like the possibility of a new love.

It could be a little smile, some exchanged glances, some witty banter, and just like that, it feels like a spell is cast.

Now, that spell might last a lifetime, or it might only last long enough to get us to the next train stop.

But either way, we're gonna walk away with a story to tell.

♪ ♪ GREY: My name is Jack Simon Grey.

My pronouns are they, them, theirs.

I currently live in Cambridge, Massachusetts, although I spent the first 18 years of my life in Dallas.

And then by day, I'm a bureaucrat, and by night, I do stand-up comedy.

And given that this is your first time storytelling, what impact do you think this experience will have on your comedy moving forward?

GREY: So, because I have an improv background, I'm used to getting my jokes 80% of the way there.

And then we step onto the stage, and we see what's happening.

Right?

OKOKON: (chuckles) Like, I come in with ideas and definitely prepared material, but I also value responding to the audience, and I feel like the level of polish that this experience has pushed me to have is 100% something I'm gonna be taking back into my stand up later.

And is there, like, a method that you tend to follow when you're crafting your comedic sketches together?

I look for jokes that use the mind, the heart, and the voice.

If a joke doesn't have enough mind, as in, there's not a fact or something interesting to engage with, I'll try to bump that up a bit.

OKOKON: Mm.

If there's not enough heart, then I'll see, "Well, how do I feel about this?"

You know, "Where is this taking me?"

And voice, I just like doing silly voices.

(both laughing) I've been told I have a very expressive voice quality, and it's something I love to leverage in my stand up.

I remember the first time I saw Emily with her long, chestnut brown straight hair and big brown eyes.

Without even knowing her, she seemed to exude brightness and warmth.

We met at a book club, a feminist book club, which, in my opinion, is one of the most romantic places you can meet somebody.

I found Emily to be the most incredible book club member.

She had some of the most astute observations about some of the books we all read together.

And she even made an incredible suggestion for a book to read, a book of poetry-- I had never really been into poetry before-- by a non-binary author named Andrea, sometimes Andrew, Gibson.

Now, at the time, I definitely felt the tiniest glimmers of what I called admiration for Emily.

But at the time, I was also in the middle of a job search, and I was trying to figure out a few other things in my life, and my focus was decidedly elsewhere.

One day in early January 2020, a member of our book club suggested that we go dancing.

As in, take our book club to the "club" club.

(laughter) A bit of an out of character switch up, for sure.

But I like dancing and it was a queer night, so I agreed to go.

In the days leading up to the event, one by one, each of our book club members drops out, until it was just me and Emily and the organizer.

And then Emily and I arrive at the club, and the organizer suddenly drops as well.

So it just became me and this wonderful, admirable person.

Now, this is a club.

So the line to get in was an hour-and-a-half long.

At this point, it is February and it is freezing.

But I found I didn't mind the cold, because Emily and I spent the entire time talking.

I learned that she's a scientist, a successful one at that, who had completed both a PhD and a postdoc at Harvard, and was founding her own biotech company.

I learned that she was relentlessly strategic.

She had taught herself how to play Magic the Gathering in order to better network with her nerdier male colleagues.

(laughter) Now we get into the club and I order us each a beer and a shot of tequila because when in club... (laughter) And I have to say, before this experience, I didn't have any intention of kissing Emily.

She was a book clubber.

In my world, feminist book clubbers do not kiss other feminist book clubbers.

When we all got together talking about whatever we read, it was such a cerebral academic experience that I was able to ignore matters of the heart.

But after the beer and the shot of tequila, I now wanted to kiss Emily and they wanted to kiss me back.

The next morning, I wake up to a text message.

"Hey, Jack, last night was super fun, but, you know, "we could just chalk up what happened to the tequila and we could go back to being friends."

I reply, "We could do that."

(audience laughter) I also happen to have two tickets to go see Andrew Gibson next week, the poet you recommended for the book club, and I'd like to go with you.

Now, that's a little bit of a lie.

(laughter) You see, I had known about this event for a month and thought about picking up tickets, but hesitated and the show was sold out.

But there was a waitlist and the idea of going with Emily made me feel optimistic.

She replies, "Why don't we go as friends and we'll see where this goes."

The next day I get an email letting me know I'm off the waitlist.

I pick up the tickets and I feel excited.

I'm going to be able to see this poet with Emily.

The night of the poetry reading rolls around and I'm sitting at the bar outside of the venue getting increasingly nervous.

I feel very out of my element.

I'd spent the better part of the last ten years reading nonfiction and webcomics.

Poetry is not my domain.

And this person is a Harvard-educated scientist.

At the time, I was just a barista hoping for my "user research portfolio" to catch on somewhere.

Emily shows and we don't kiss.

We simply say hello.

We go find our seats, and within moments, the poet takes the stage.

They walk up to the microphone and they simply announce, "Tonight is a night about love."

It was literally titled, "Right now I love you forever."

(audience laughter) The poet is launching into a poem about their partner, and I feel the tension in the room skyrocket.

This is either about to be the most awkward experience of my life or the most romantic.

I am desperately trying to not look at Emily, fearing that I would pop.

Instead, I look all around the room and all I see are couples and friend groups-- in retrospect, polycules-- everywhere.

(audience laughter) Holding each other.

The only anomaly in the room is this woman seated across from me and Emily with a conspicuously empty chair next to her.

I almost feel envious of that empty chair.

At least there was an answer, a sign that things didn't work out and one could grieve and move on and not be at a poetry reading with a "friend," feeling increasingly uncomfortable.

Suddenly, I look down, and placed very prominently on the seat next to me, I see that Emily has laid out her hand, clearly to hold.

I take a sigh of relief, and I take her hand and I pause.

The poet is speaking.

My heart is thudding so loud in my chest, I can barely make out the words, and yet I can understand what they mean, even in my body.

I put my arm around Emily, she puts her head on my chest, and together, we have one of the most romantic evenings.

There was a lot of things that happened in the story that felt very convenient.

The surprise tickets to the February 10 date of this poetry reading, the long line in the cold, and even the way that everyone dropped out.

It almost felt like fate.

But I can say that the best decision made was Emily's choice to hold my hand and my own to take hers.

Thank you.

(cheers and applause) ♪ ♪ SMITH: My name is Terrilynn Moore Smith.

I'm from Aurora, Colorado.

I am an author.

I am a storyteller and an artist.

What are your favorite types of stories to tell?

I love telling stories, especially from the African diaspora.

But my favorite story to tell is a Gullah-based story called "The People Could Fly."

It talks about the power of African religion.

It talks about keeping culture even under adverse circumstances, and it talks about the power of miracles.

I went to a friend's house to do storytelling for her big party that she has every summer, and one of the people in the crowd came up to me after I told the story, and he said, "I love that story.

"You told it at East High School in Denver "over 30 years ago, and I will never forget it."

And that is the power of storytelling.

So what are you hoping that tonight's audience remembers or takes away from your story?

Never give up hope.

Don't become resigned because things haven't worked out yet.

(chuckles) There's always another day.

There's always tomorrow.

♪ ♪ I am a Black woman who was labeled a "Negro student" in a nearly all-white junior high in Colorado.

I was sometimes isolated and often afraid.

It was in these difficult circumstances that I met Quade Smith, in 1970, when we were both 14 years of age.

Quade was tall, freckled, and handsome with his sparkling blue eyes and horn-rimmed glasses.

He was nice to me in an often hostile situation.

Quade was especially impressive, because of at the age of 14, he had already climbed all 53 of the Colorado Rocky Mountains that are over 14,000 feet in height.

(chuckling): Quade was amazing.

He had done all of this when he was just 12 years of age with his father and three brothers.

They are known as the Climbing Smiths.

They were sometimes featured in the Empire magazine that came to our house on Sundays.

Quade asked me out on one date.

His dad, George Nash Smith, dropped him off at my house.

Quade nervously entered our home.

And my dad, James Alvin Moore, a Denver police officer... (audience laughter) ...acted just like a sitcom dad, making sure to scare the pants off my 14-year-old suitor.

(laughter) I don't remember what we did on our date.

I do know that Quade did not ask me out again.

But I pulled up my big girl panties and asked him out on a date for the Sadie Hawkins Day Dance.

Quade turned me down.

My heart was bruised.

I didn't know why he wouldn't ask me out again.

Was he afraid to date a Negro girl?

It was a long time before I saw him again.

So, in 2019, I was absolutely shocked to get an invitation to our 45th high school reunion.

I was nervous.

I said, okay, I'm gonna do this.

So I wiggled into my Spanx... (audience laughter) and I drove to the gathering.

It was amazing to run into friends that I had not seen in 45 years.

I regaled them with tales of my having been a police officer for ten years for the city of Denver, Colorado.

I was the very first African American woman to be transferred over to the gang unit.

As I'm telling this story, Quade is actually in the crowd listening to me.

I didn't recognize him, but I did see this man with snow white beard and sparkling blue eyes and I thought, "Oh my goodness, he is handsome."

And Pam Livingston pipes in, "Isn't it so nice to see Quade Smith?"

And my heart nearly stopped.

Quade Smith, my junior high crush, is here?

Quade asked me out that evening and I found out he was even more impressive now.

By now, he had climbed over 350 of the world's mountains that are over 14,000 feet in height.

He was retired, he had helped his dad write his book.

And now, he's talking to me.

He kept asking me out.

We went hiking, and to the movies.

We just talked for hours.

He took an interest in everything that I did.

He even went with me to my mother's Alzheimer's care facility, to visit a dotty, frail old woman.

But then he came over to my house on a very cold winter's day and he slipped on my front porch and he heard a loud pop and he hobbled back into the house.

He asked me to bring him an ice pack.

I immediately grabbed that.

The next day, I drive him to urgent care.

The people at urgent care said "You need to see your doctor."

We go to the doctor's office.

The news is not great; Quade had broken his fibula.

Surgery was scheduled for the following week.

I immediately moved out of my house and into his house to nurse him back to health.

Besides, I was afraid he could sue the pants off me.

(audience laughter) Oh, this accident was serendipitous, to say the very least.

Eating, living, laughing, and loving together was an absolute gift.

It allowed me to get to know a beautiful, well-rounded human being.

Quade expressed interest in marrying me.

Ha!

He took me to his favorite jewelry store and had me help him pick out my ring.

The ring was delivered several weeks later.

He didn't know that I'd seen it be delivered, and he didn't know that I'd seen him put it away.

But he didn't propose, and he didn't propose.

Another month and another month go by, and I got nervous.

I was a nervous wreck.

Had he changed his mind about marrying me?

Then one night, he pops up out of bed.

He's rumbling around in his dresser drawer.

He comes back to bed, and I must tell you, he was wearing his very best outfit-- nothing at all.

(audience laughter) (laughing) So, he pops back into bed, and he looks at me earnestly.

He says, "You are my very best friend.

"And my go-to person, "and I want to spend my life with you.

Will you marry me?"

(sighs) I laughed.

(laughs) And of course I said yes to the naked guy.

(laughs) So, on the spring equinox in 2023, I got to say "I do"... (crowd says "aww") ...to my very best friend.

And I must tell you, I absolutely believe in the power of Cupid's arrow.

And I am absolutely smitten.

(cheers and applause) ♪ ♪ STEWART: My name is Zach Stewart.

I am 30 years old.

I live in Watertown, Massachusetts, and I work in quality assurance for a biotech company.

And I understand, like, from storytelling, you've sort of moved into stand-up comedy, and you're, like, a bit of an up-and-coming comedian in the Greater Boston area.

Can you tell us a bit about that and about how that transition happened?

STEWART: About two years ago, I decided to take a stand-up class, and I really loved it.

I just loved the freedom that I had with stand-up versus storytelling in terms of being able to talk about whatever I wanted or transition, and trying to kind of merge those two spaces.

Mm-hmm.

STEWART: And I've really grown to love it as, like, an artist and creating something on stage, but also as a producer, giving opportunities to other queer comics in the area.

So can you talk about what impact you're hoping to have in the queer community through the comedy shows that you are producing?

I'm hoping to give more visibility to all of these performers.

There's so many amazing performers in Boston that are queer that are really doing some groundbreaking things in comedy, and it's hard for them to get the amount of stage time as some of their straight counterparts.

Mm-hmm.

Also, I want to develop this audience that feels connected to stand up comedy, that's rooting for us, that's creating a fan base.

♪ ♪ I love romantic comedies.

My favorite in college was Sex and the City, and I never thought it affected my dating until I saw my laptop, and it was full of folders and files on notes of every guy I dated in my twenties.

Like a gay, unpublished Carrie Bradshaw.

(laughter) I needed to collect every little piece of data so I could, like, regale my tales to my friends at brunch.

Like, I never dated Charles or George.

I dated the guy whose feet kind of smell.

(laughter) It was only until they proved their worth is when they were granted names.

This is a story about wallet guy.

(audience laughter) Wallet guy and I met over a dating app, and he had asked to do a FaceTime date before we met.

And it was kind of weird.

There were a lot of awkward silences, and I didn't really understand his humor, but I didn't really think we were gonna see each other again.

And he texted me the next day to go on a date.

We go to his apartment to watch reality tv and eat takeout, and I'm starting to understand his deadpan style of humor.

And he's telling me all about his mom, and I just know she's gonna love me, you know?

(audience chuckles) And it's crazy 'cause he's a resident at a local hospital, and a psychic once told me I was gonna marry a doctor.

(audience laughter) I don't know, it seems like fate.

And the whole time, my mind's kind of in two places.

I'm, like, looking at him and I'm thinking, like, am I smiling?

Am I smiling too much?

Is this a sad story?

Should I look more empathetic?

Am I nodding?

Am I nodding too much?

And I think it's because I'm not fully present on the date.

Because since I walked into his apartment, past the concierge, up the eleven floors to his apartment that viewed all of Boston Common, I knew I had met my husband.

(audience laughter) I was already befriending the concierge.

I was rearranging the furniture.

(laughter) I was planning dates with my friends to go to the park and then go back to my-- I mean our-- apartment.

(audience laughter) The date went great.

He walked me to the door, he gave me a kiss, and he said, "I'll see you later."

I get to my car, and I don't have my wallet.

And I'm looking through my car, but then I realize I paid for metered parking with my debit card inside wallet.

So I go back upstairs and we start going through his entire apartment.

We're flipping couch cushions, we are raiding the fridge.

We are going through the medicine cabinet.

It is nowhere to be found.

Eventually, he looks at me and he goes, do you think I stole the wallet?

Which I hadn't thought of till he said it.

(laughter) But I honestly did not care if he was a wallet thief.

I just didn't want him to think I thought he was a wallet thief.

'Cause, you know, this is just a blip, you know, his money, my money.

(laughter) Soon it will be our money, and we can just laugh about this.

(laughter) So we look through the apartment again, and we can't find the wallet.

So I go home, and at this point, like, the anxiety of ruining the date is worse than the anxiety of losing the wallet.

He texts me the next day and says he found the wallet.

And I was like, "Oh, when can I come pick it up?"

And he goes, "Oh, whenever.

I'll just leave it with the concierge."

And I quickly respond, "I'm good to get it whenever... ...you're free."

Because I think this is our second date, right?

This is my romcom moment, people.

(audience laughter) This is a little bump in the road.

And then we all laugh about it.

And then three to five years from now, bam; I'm a doctor's wife.

(laughter) It's been five days.

Wallet guy has been tied up at the hospital, which is something that I'm gonna have to learn to get used to.

(audience laughter) I have no cash.

I work from home, but my car is out of gas, so I'm just ordering Grubhub for every meal.

The same driver's at my door, day in, day out.

(audience laughter) I have not seen any friends.

I have not been up to much, and I'm noticing that wallet guy's responses are getting kind of shorter, and it's taking him longer to respond.

And I'm like, is this a weird vibe?

And then I realize, what if he thinks I planted the wallet?

Maybe I did-- like, not, consciously.

(audience laughter) But what if subconsciously I planted it?

Or what if I saw it while we were looking for it, and I just, like, ignored it?

Like, what if instead of this being a romcom, this is a psychological thriller, and I am the villain?

(laughter) What if I'm Glenn Close in Fatal Attraction?

(laughter) But I had to Grubhub the rabbit soup?

(laughter) And, like, I do not know if things unraveled because I was weird looking for the wallet.

I don't know if he thinks I'm some sort of mastermind that had left breadcrumbs back to the second date, or I don't know if he just didn't like me that much and didn't want to see me again.

But I knew that I wasn't going to figure that out daydreaming and fantasizing about what we could have had.

So I text him that I did, in fact, need my wallet.

The next day, I go to his apartment.

He hands me the wallet, gives me a two finger salute and sends me on my way.

I think about wallet guy a lot.

Not about being with him.

Being a doctor's wife seems very stressful.

(laughter) But I do think about how I was when I was with him.

I was willing to bend over backwards to be the kind of person I thought he wanted, when I didn't even know him.

I can't lie to you people and say that when I talk to someone, I don't jump three to five years into the future.

But I do try to keep my feet on the ground and my wallet in my pocket.

(audience laughter) Thank you guys so much.

(cheers and applause) ♪