When I was in college in Boston, I matched with a guy from Harvard. He mentioned it often—casually, not quite a red flag, but definitely a recurring theme. I didn’t care much. I’d grown up on the Dartmouth campus, so the Ivy League mystique had worn off long ago. We agreed to meet for dinner, and things started off fine. But when the waitress came, he tried to order for me without asking. I politely corrected her, and he explained he “knew what was good” since he’d been there before. That was the first sign. The rest of the night confirmed it.
He spent the entire meal talking about Harvard—how great it was, how impressive he was, how lucky I was to be sitting across from him. He never asked a single question about me. Every time I tried to steer the conversation elsewhere, he looped it back to himself. I learned about his professors, his internships, his future plans. I didn’t learn anything about his character. It was like dining with a résumé. I nodded, smiled, and counted the minutes until dessert. I’d never felt so invisible while sitting in plain sight.
When the bill came, I offered to split it. He looked genuinely offended, as if I’d insulted his legacy. I insisted, and he reluctantly agreed. As we left, he placed his hand on my back to “guide” me out of the restaurant. I recoiled instinctively. It wasn’t the gesture—it was the entitlement behind it. Outside, he leaned in for a hug. I stepped back and said, “Thanks for dinner.” That was the end of it. No second date. No lingering curiosity. Just relief.
I can’t remember his name now, which feels poetic. He spent the whole evening trying to impress me, and left no lasting impression. I do wonder if anyone ever found his arrogance as attractive as he did. Maybe someone out there mistook it for confidence. But for me, it was a masterclass in how not to connect. Charm isn’t about credentials—it’s about curiosity. And he had none. Just a spotlight he refused to share.
Looking back, I’m glad I went. It taught me to trust my instincts, to value mutual interest, and to recognize the difference between prestige and presence. I’ve had better dates since—ones filled with laughter, questions, and genuine connection. That night reminded me that being impressive means nothing if you’re not also interested. And that no Ivy League name can substitute for basic kindness.
So here’s to the dinner dates that teach us something. To the quiet exits, the firm boundaries, and the freedom of walking away. To knowing our worth, even when someone else can’t see it. And to the reminder that the best conversations are the ones where both people matter.
