Sharing Stories of Breakups and Bad Dates on Valentine’s Day

Sharing Stories of Breakups and Bad Dates on Valentine’s Day


For every hopeful story of love, there is a crushing tale of pain. For every soaring moment, an awkward stumble. If Valentine’s Day is a celebration of love in its entirety, shouldn’t we acknowledge the dark side of romance too?

On a frigid February day, we made our way from Midtown Manhattan to City Hall, wandering into food halls and shopping centers for warmth and asking strangers to tell us about their worst dates, breakups and Valentine’s Days.

There were plenty of tales of woe and sadness, but they were told with humor and hope. We took comfort in the words of one woman, who was sunbathing in full winter gear in Bryant Park (but who, sadly, did not want to be photographed). “The great thing about getting old is you can forget all the bad stuff,” she said.

And in the meantime, know this: We’ve all been there.

CreditKrista Schlueter for The New York Times

Patrick Smith, ‘25 to 54’

Driver, Queens

What’s the worst thing that you’ve witnessed in this car?

I had this bride and groom, and I guess he wasn’t following the directions he’d been given because he took forever to get to the church. He was waiting for his family. His bride had said, “Forget about your family. You get there on time. Get there first.”

After the wedding, her and him got in the car and we drove out to a spot by a country club, and she cursed him out. And then when she was finished, she said, “O.K., let’s go back to the church.”

CreditKrista Schlueter for The New York Times

Elyse Fox, 28

Activist and filmmaker, Brooklyn

What is the worst Valentine’s Day you’ve ever had?

I was with my ex for about five years. He was being so secretive that I thought he was hiding something cool and it was going to be a big surprise. And I came home and there was nothing.

Was that your last Valentine’s Day together?

Yes. It certainly was.

What’s the worst date you’ve been on?

I went on a date with this guy. He asked me maybe one question, “How are you?” And from then, it was only about him. Sometimes he still reaches out to me. He texts me to brag about himself.

What’s the worst breakup you ever had?

My ex was cheating on me for a good amount of time. Whenever he did something sneaky, he would come home with a lobster dinner for me or other really big things. I pieced it together.

Was that the same guy as the one who didn’t plan anything for Valentine’s Day?

Yes.

CreditKrista Schlueter for The New York Times

George Taxi, 48

Flower guy outside the Marriage Bureau, Brooklyn

What was your worst breakup?

When I was in high school, I broke up with a girl because I had a fire in my house. I really didn’t like her much, so I used that as an excuse. “My house went on fire, I lost everything, my head’s not right.”

How did she take it?

Not well.

So your worst breakup was perpetrated by you?

Well, one woman broke up with me over the phone the day after Christmas.

How was that Valentine’s Day?

I was pretty brokenhearted. The day didn’t matter.

CreditKrista Schlueter for The New York Times

London Brison, left, 22, and Kameron Porter, 23

Dancers, Brooklyn and Atlanta

What’s the worst Valentine’s Day you’ve had?

Mr. Porter: I got a hot-air balloon for my girlfriend, and she hated it. We went up for about 10 minutes and she yelled, “Take me down, I hate this.” She broke up with me as soon as we got to the bottom. I still had to pay in full. It was $150. For 10 minutes.

What’s the worst breakup you’ve had?

Mr. Brison: Believing in it so strongly and then both of us realizing that it’s not working at the same time. It was hard fighting that and not coming to terms with it. We knew we couldn’t do it, but we were trying to.

How long were you with this person?

A year.

And how long did it take to break up?

A year. But really, though, it was a good relationship for six months and then paths changed, careers changed.

CreditKrista Schlueter for The New York Times

Jack Crosley

‘Old enough to have gone to college in the ’70s,’ performer and officer of the courts, Manhattan

What is the worst date you’ve been on?

I knew this girl in college. Years later, some guy is riding a bicycle down the street. “Are you Jack Crosley?” I’m like, “Yeah.” “My roommate has pictures of you all over our house.” She was a photographer.

“Really, what’s her name? I remember her. Give me her number, I’ll call her up.” I call her. She says, “Wow, I can’t believe it.” I pick her up at her place for a date. We go to a cocktail lounge on St. Marks Place. That’s just the first stop. I had a whole evening planned.

I go to the bathroom. I come back and she’s talking to some other guy, who was a real loser. She goes, “Me and Sammy are going to have sushi. Do you want to come?” I made it very clear: “You two go off. I had a whole night planned, and I can do it without you.”

What’s the old saying? “I can feel alone and alienated without your help.”

CreditKrista Schlueter for The New York Times

Jonnesha Bellamy, 21

Retail merchandiser, Charlotte, N.C.

What’s your worst Valentine’s Day memory?

Two years ago, I was talking to this guy and I got him a gift. A big six-foot bear and some candy. Then we broke up a day before Valentine’s Day. So I spent all my money for nothing. The bear was like a hundred dollars. I still have it.

At least you had the candy.

Yeah, that was a benefit.

CreditKrista Schlueter for The New York Times

Gavin Pomerantz, 25

Artist developer, Brooklyn

What is the worst date you’ve been on?

I brought a girl to a Japanese performance art show, and she wasn’t really digging it. And she just kind of left. We were in Red Hook, so it was far away, too.

Were you upset? Did you offer to leave with her?

No. Nothing really affects me in that kind of way.

What’s the worst breakup you’ve gone through?

My first breakup ever. I was in high school. I thought I was going to marry this girl. She was the first girl. I lost my virginity, everything. One day she was like, “I don’t want to do this anymore.” I lost complete trust in people for a while.

CreditKrista Schlueter for The New York Times

Hilary Yeh, 24

Artist’s assistant, Queens

What was your worst Valentine’s Day?

Two years ago. I had just gotten out of a relationship, and we had been together for three years.

Did you celebrate the holiday as a couple?

When we started dating, we were still in college, so I think we were too young to properly celebrate it. I grew up with divorced parents and neither of them ever remarried, so I wasn’t introduced to that type of tradition.

What’s the most awkward date you’ve been on?

First dates are always quite awkward. I’m a slow burner, so it takes me a lot of time to be socially comfortable with somebody, especially if we’re there for the purpose of having an intimate relationship. But I don’t think any awkwardness can’t be fixed with time.

CreditKrista Schlueter for The New York Times

Lavar Hernaiz, 33

Cleaner, Bridgeport, Conn.

Are you a fan of Valentine’s Day?

I’m not into Valentine’s Day. Every Valentine’s Day I’ve been alone. Except when I was younger.

Who were you with then?

I dated a girl for like 15 years. We have two kids together.

Did you two have any awkward romantic moments?

We were in a park in front of her house, and we had two feet of snow that day. I couldn’t go in her house. Her mother didn’t want me to. So I put our names in the snow in real big letters so the airplanes could see them. After I did that, I tried to really impress her by jumping off the bench and doing a back flip. I landed on my back.

CreditKrista Schlueter for The New York Times

Lauren Graham, 35

Photo shoot producer, Brooklyn

How do you feel about Valentine’s Day?

I was single for so long, for eight years, so it was kind of silly. Now I’m married, but I’m always gone for work on Valentine’s Day.

What’s the worst date you’ve been on?

I had an awful Tinder date. You never sign for a dinner first, but I did. While we were waiting for appetizers, we started talking about politics. He said, “Are you liberal?” And I said, “Yeah, and I don’t want a bunch of men telling me what to do with my body.”

He said, “Well, honestly, though, how many rapes end with children?” And I thought, Oh no, I don’t want to be here anymore. I kind of nodded at everything after that. But I also kind of said my opinion on everything because I didn’t care anyway. What did I have to lose?



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