The good, the bad and the funny: Brooklynites share their dating stories ahead of Valentine’s Day

valentine's day dating stories
Brooklynites reflect on their dating highs and lows ahead of Valentine’s Day.
Photo courtesy of Katerina Holmes/Pexels

Valentine’s Day is right around the corner, and Brooklynites are getting in the mood by reminiscing on some of their best, worst and most memorable dating experiences, to say the least. Nearly three million people call Kings County home — and with that, comes a lot of good, bad and laugh-out-loud funny. (See also: cringe.)

Here are some dating horror — and success — stories, to get you in the V-Day spirit.

The good

Not all dating stories end in tragedy.

Brooklynite BelRaye Osborne told Brooklyn Paper that she ended up marrying her childhood sweetheart after meeting in a church choir. Osborne and her husband, Tru, grew up knowing one another but it wasn’t until she told a friend about her crush on him that they started seeing each other more seriously. 

The pair recently celebrated their seventh anniversary with dinner at Joya, a Thai spot in Downtown Brooklyn — and one of the first spots they went to when they started dating. 

Osborne said that, since they’re both big foodies, Brooklyn restaurants are at the core of their relationship. 

“It was like we were recreating those memories and Brooklyn restaurants are a big part of that,” she said. 

Valentine's Day - BelRaye and Tru Osborne have a first date that ends with a happily ever after.
BelRaye and Tru Osborne’s first date ended with a happily ever after. Photo courtesy of BelRaye Osborne

The Osbornes now work at the same East New York school, have a life-coaching business together, and are even planning to release a joint music project soon. They’re also raising their children, Titan, Thunder and Temple — who they delivered on the side of the road together in a wild once-in-a-lifetime experience.

When asked for dating advice, Osborne said she would tell local singles — especially those on online dating apps — to learn to love themselves before really figuring out what they want in a partner.

“It was important for me to make sure I knew my worth and my values. Self-love has to be a priority,” she said. “Be you. Go for it, as long as you are making sure you are doing what’s authentic to you.”

The funny

Brooklyn musician Martin Vaillancourt recalled a first date that left him and his partner a little uncomfortable, but ultimately revealed a similar, sinister sense of humor.

Vaillancourt, a white man, and his date, a Black woman, went to a comedy show for their first hang. The pair was late to the show, forcing them to sit in one of the front row seats where each comic took a shot at them during the crowd work.

Martin Vaillancourt shared a laugh with his date that turned into a memorable dating experience.
Martin Vaillancourt shared a laugh with his date that turned into a memorable experience. Photo courtesy of Martin Vaillancourt

The musician said it was all fun and games until one comic started asking more questions about him and his date, including where they met, how long they’ve known each other and what they did for work. Vaillancourt — who worked at an auction house at the time — told the comic so, and he fired off with a joke about slavery.

“So is this some type of slavery kink?” Vaillancourt recalled the comic asking.

“Everyone laughed and she took it like a champ,” he said. “If anything, the joke brought us closer because it was hysterical and so jarring.”

The duo later decided to split, but not without a hilarious first date story. 

The (pool) obsessed

Natalia Gaytan’s most memorable first date shows just how unique Brooklyn’s bar patrons can be. What started as a night out at a Williamsburg watering hole ended in a date with a pool-obsessed Brooklynite looking to shack rack up.

“I was alone watching some dudes play by a pool table when one of them came up to me and we started chatting,” she said. “He ended up telling me that he only ever went to that bar because he wanted to prove he was the best at pool.”

Gaytan bonded with a man she met at a pool bar but that turned out to be their only common ground.
Natalia Gaytan bonded with a man she met at a pool bar but that turned out to be their only common ground. Photo courtesy of Natalia Gaytan

The two ended up going out four more times — each time at another pool bar, where Gaytan said her date would spend the entire night trying to prove himself to other players. Eventually, the pool shark struck out.

“He was interesting but I wasn’t interested by the second date,” she said. “I just kept saying yes, hoping the pool obsession would go away.”

The confused

Amber Rhae Dycus matched with someone she said was “very sweet,” but their first rendezvous ended in what she called an “ethnic misunderstanding.”

Dycus, who is Native American and Chinese, matched with a guy who thought they shared ethnic backgrounds. To celebrate their common upbringing, her date planned for the two to go to an Indian restaurant. She said the conversation came to a halt when he realized she was Indigenous and not South Asian.

“He wanted to take me to a place that would remind us of our Asian roots,” she said. “To say the least, he was surprised and upset.”

A case of mistaken identity made Dycus feel like maybe he wasn’t what she was looking for but she still reached out to thank him for a great date. “A few weeks later, he responded [that he also] had a great time but it would seem we don’t have much in common and I truly wasn’t his type after all.”

The straight-up bad

Alexis Hutchinson’s most memorable first date proves that persistence isn’t always rewarded. The Brooklyn-based writer matched with someone on Hinge, and decided to give the guy a shot.

On the way to a restaurant where she made reservations, he texted her to say he was stopping at Chipotle because he was hungry. Hutchinson rerouted to meet him for dinner, only to find out he was already eating by the time she got there. 

Poor manners aside, Hutchinson says the conversation fell flat — but things really came to a head when her date made an interesting confession. Hutchinson’s date told her he worked in tech, but that he wanted to make his living creating clothes for felines, because, “cats need clothes, too.”

Alexis, a Brooklyn-based writer, takes the cake with the most jarring first date experience.
Brooklyn-based writer Alexis Hutchinson’s story proves that persistence isn’t always rewarded. Photo courtesy of Alexis Hutchinson

“At this point, I’m over it, but I persisted,” she said. “I tried to have a normal conversation but instead he’s singing, tapping on tables, telling people their food looks good and digging his hands in my plate.”

The pair finally made it to the original restaurant, where her date racked up a $70 bill she got stuck paying. Hutchinson was ready to call it a night but she had already purchased movie tickets for them both, so she persisted once more.

“At the theatre, he is talking full volume throughout the movie,” she said. “I was fed up but I kept going.”

Next up was an interrogation into Hutchinson’s romantic history, her friend group, and on whether or not she found Jared Leto attractive. Hutchinson said her breaking point was when he got upset that she said she has a lot of Black female friends.

An annoyed Hutchinson finally made her great escape into an Uber — but not before Mr. Moocher told her that he had a great time and would like to see her again.

The nitty-gritty

According to the U.S. Census, roughly 2,590,516 people consider Brooklyn home, making it a jungle for those looking for love. While more people could mean more options, Rabbi Dr. Jack Cohen, a dating coach in the borough, said this could actually make it harder to date.

“Modern dating is harder than previous generations because of too many choices,” he told Brooklyn Paper. “At your finger, you have access to thousands and thousands of resumes. You’re never happy.”

Cohen broke down what it’s like to date in modern culture and shared some common trends he sees.

“People are looking for someone to add to their life. No matter how successful you are, you are looking for someone to share your life with,” he said.

valentine's day dating
Looking for love is even harder than it seems in a borough as populous as Brooklyn, according to one dating expert.Getty Images

He advises his clients to first write down what they want in a relationship, then analyze themselves and the person they are dating to figure out what questions to ask them. Most importantly, he reminds them to date with their heads and not just their hearts — especially if they are looking for a longterm relationship. 

“If you know how to ask the right questions, then you should know if the person is for you after two or three dates,” Cohen said. “Marriage requires sharing time, space, money, and attention. To get married you need to be able to sacrifice.”

Whether Brooklynites are looking for a forever match or just taking things slow, Cohen said the best matches come down to a “soul connection.”

“Can you handle their imperfection? Do you admire them? Do you admire their aspiration in life,” he said. “There’s a soul connection and that’s critical.”