Girls, have you ever rejected someone but then regretted it?

This isn’t my story, but my mom’s. She still talks about a college classmate who eagerly courted her, but she turned him down for years. Eventually, he started dating another girl, and they’re still together with a beautiful family, living happily. The guy — still good-looking — tells my mom at every reunion that he would have made her the happiest woman in the world. Once I asked my mom why she rejected him, and she said, “I couldn’t date a redhead!”

He was a sweet, kind guy, but the timing was off—I was swamped with exams and couldn’t fit in a date, let alone a relationship. A month later, he started dating my best friend. His startup became so successful two years later that he sold it and now all they do is spend money. They post photos from the Maldives, and I keep wondering why I didn’t say yes to that date back then.

I didn’t give him a chance solely because my parents suggested I date him. He was the son of my dad’s colleague and was introduced to me a bit awkwardly at a garden party. We were in our twenties, he was tall, handsome, and nice, but I felt embarrassed that my parents were matchmaking, so I showed no interest—and I still regret that.

Things were going well, but he said "I love you" too soon, so I told him it was moving too fast for me. Today, he’s a successful doctor who regularly travels to Africa to operate on children and dotes on the girl he dated after me.

I didn’t give a decent man a chance because I was head over heels for a useless alpha jerk. The man tried for years without success, then one evening sadly told me he couldn’t wait any longer. I thought it was so childish and dramatic. Today, he’s raising three beautiful kids with his lovely wife, and I’m single at 45, doubting I’ll ever have a normal, loving relationship after the trauma caused by that alpha.

He was smart, funny, and kind, but he didn’t look good—he had acne, wore glasses, and was a bit chubby. Meanwhile, the school heartthrob was chasing me, and I married him. At our 20-year reunion, I showed up with my bald, out-of-shape husband, while he arrived tall, fit, glasses-free, with thick hair, wearing an expensive suit and arm-in-arm with a stunning woman 20 years younger. I guess that’s what karma looks like.

I rejected him because I knew he’d been intimate with his ex, and I wasn’t ready for that yet. Years later, we ran into each other (he looked better than ever and had a successful company), and I told him my concerns. He said he was so in love with me he would have waited years until I was ready. He’s now engaged, so that ship has sailed.

We were best friends, he confessed his love, but I didn’t want to risk our friendship. We lost touch, got married, then divorced. I ran into his ex-wife at a concert; she said they divorced because she knew he still loved me. The next day I called him, and we tearfully planned to meet—but he never showed up. That morning, he had a heart attack and passed away.

I rejected him because he asked for my number in front of my friends, and I got embarrassed, thinking it was cooler not to give it. He’s now a famous singer, and I keep banging my head against the wall whenever I see him on TV.