In today’s dating world, everyone has a story to share. But some stories are memorable not just for the laughs, but for the surprising twists they take. Recently, we got a story from a young woman in New York who thought she’d met the perfect match on a popular dating app. Their expensive first date seemed like it would be romantic, but things took an unexpected turn. What started as a funny dating mishap quickly turned into a surprising discovery, leaving her wondering if she’d judged him too soon.
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“I met this guy on a dating app. When we matched on the app, he seemed perfect. He had this all laid-back confidence, and a profile that was actually funny — a unicorn on dating apps. He was adventurous, loved dogs, and had a playlist that could rival mine.”
“We started chatting, and I don’t know how, but we immediately hit it off. Inside jokes were piling up, and soon it felt like we’d known each other for ages. He even remembered my favorite coffee order and joked he’d have it waiting on our first date. So, yeah, my hopes were high.”
“And at first, it all seemed...dreamy. He invited me to one of the best seafood spots in NYC, the kind of place with a waitlist that could outlive your favorite pair of shoes. I was 20 minutes late (classic), and he even waited outside the entire time just so I wouldn’t have to sweat it out trying to find the place.”
“The moment I arrived, he was charming and warm, all smiles as he opened the door for me. He even helped me out of my coat like he was some gallant gentleman from a black-and-white movie. I thought, ’Wow, maybe I’ve finally found someone who’s different.’”
“Then we sat down, and for the first 15 minutes, everything was perfect. We ordered, shared some laughs, and I felt that hopeful little buzz you get on a really promising date. The evening had all the right vibes. So, to see if we were actually compatible, I casually asked what kind of partner he was looking for. And, well — that was his trigger.”
“His face shifted, like I’d flipped some hidden switch, and suddenly he was off. He spent all dinner talking about how ’ungrateful’ his ex was. He detailed date after date where he’d ’gone above and beyond’ for her, and how she’d dared to break up with him. It went on and on, like an episode of some terrible dating reality show. My optimistic heart started to sink like the Titanic, but I kept thinking, ’Maybe he just needs to vent?’”
“By the time he started criticizing her Christmas gift ideas, though, I knew. This was not the magical, expensive first date I’d been dreaming of. The funny, charming guy I’d been talking to vanished, replaced by someone who looked ready to testify in court.”
“That’s when I knew it was our last date. I told him upfront that discussing exes is taboo for me. And offered to split the bill, because the bill was a whopping $700, but he refused, insisting that the girl shouldn’t have to pay the bills.”
“A few hours later, I got angry texts from him saying he was ’done with women who couldn’t appreciate a real man.’ Oh, please. A real man doesn’t spend an entire dinner going on about his ex! I texted him back, politely (or as polite as I could be while borderline fuming) and told him, ’Look, I think we just have different expectations. Good luck!’”
“Thought that would be the end of it. But nope. Cue the paragraphs. He started calling me shallow and selfish, claiming I ’wasn’t open-minded enough to understand his truth.’ His truth? Sir, your truth was three hours of self-pity with a side of garlic bread.”
“The next day, he texted again. Now he wanted an ’explanation’ for why I didn’t want a second date, and I thought okay. Let’s give him one. So, I wrote back, ’Honestly, I just think we’re looking for different things. Also, you spent most of the dinner blaming your ex. It’s just... not attractive.’ And I sent it. Done and done, right?”
“Wrong. A few minutes later, another notification. Now he was offended, outraged. He started listing his achievements, ’I make six figures, I own my own car, I’ve traveled.’ He ended with, ’Do you know how hard it is to find someone like me?’”
“I thought about replying with, ’Well, my friend, it looks like we both dodged a bullet,’ but instead, I just blocked him.”
“So, naturally, for the next two weeks, this became the story I told everyone. My friends, coworkers, even strangers at the coffee shop got the full saga of ’Mr. Angry Ex Rant.’ I mean, it was way too funny to keep to myself. If you’re from New York, you know how wild the dating pool is, everyone has a story that could rival a rom-com or a horror movie. Finally, I had my own gem to contribute.”
“Then I shared it with my yoga friend, expecting the usual laughs and ’Wow, he sounds terrible’ responses. But she just looked at me with raised eyebrows and said, ’Wait, I actually know this guy.’ My jaw practically hit the mat.”
“As it turned out, he really was that impressive guy I’d been so drawn to on the app. She explained that, in past relationships, he’d been put through the wringer. His ex, she told me, had drained him emotionally and financially, only to leave him for one of his own friends — a guy who just happened to be some high-powered finance exec. Apparently, she’d even cheated on him toward the end. So, yeah, *ouch*.”
“Hearing that hit me like a truck. Suddenly, his odd behavior on our date made a lot more sense, and the guilt set in fast for blocking him after the first date. Here I was, spinning him into a punchline for my friends, without any clue what he’d been through. Now, I’m at a total loss. Do I just let it go? Or should I unblock him, apologize, and maybe even suggest a second date?
I honestly don’t know what’s worse — sticking to my guns and feeling guilty, or reaching out and risking more monologues about the ex-girlfriend.”
It’s completely natural to feel guilty after learning someone’s background, especially when that context explains behaviors that initially seemed like red flags.
However, remember that everyone has their own baggage, and while his experiences may explain his venting, they don’t entirely excuse it. In healthy dating, we bring our best selves, or at least try to, instead of focusing on past wounds. His intense reaction on your date may indicate he still has unresolved pain that could affect any new relationship.
If you feel inclined to reach out, consider doing so with compassion but without expectations. You might express understanding of his past struggles, while also being clear that moving forward, you’d expect openness without lingering bitterness. If he’s working through his past, he may need time alone to heal fully.
Ultimately, follow your gut: you deserve someone who brings positivity and emotional availability to the table, as you do.
Bright Side received another heart-wrenching story of betrayal, when a husband left his wife with a newborn for three weeks and moved in with his colleague, because the baby was “too loud”.
