31.
Proposed to my college girlfriend when I was 20 and she was 21. We had been dating for a year and she got pregnant. I thought we were in love because everything was great and I genuinely loved her. I had a great job and so I proposed because I wanted to marry her and start a family. She then broke down and started crying, she told me she had been sleeping with her ex boyfriend for the past month. She then said that she didn’t know who the baby belonged to so went and got an abortion without consulting me or him. She got back together with him and I spiraled into alcoholism for the next few years.
Im about to turn 30 now, went back to college 2 years ago and no longer use drugs or alcohol (besides weed sometimes). I’m starting life over again at 30 after all that, and having to take care of my grandfather who had a stroke. Life is fuckin weird. –rapey_tree_salesman
32.
My ex girlfriend declined when I proposed a couple years ago. It was surprising because we had discussed marriage before and she said that she wanted me to propose. I even got her father’s blessing before he passed away and proposed to her surrounded only by close friends, family, and funeral home staff. I feel like I did everything right but sometimes that isn’t enough I guess. –dennismiller2024
33.
I was casually dating a guy in a rock band. He just knew he was going to “make it big” and be a rock star, and I always thought he was a little bit crazy, but heck, it was all fun and games because I was young and that’s what I was looking for. I loved to follow his band and dance the night away on weekends, partying with my friends in whatever nightclub he was playing, a great way to forget about school and studying for a few hours. When he popped the question, I was so surprised I burst out laughing! I was 22 years old, just graduated from college and was about to start my career. I was starting an internship and was leaving the country for a year, and he asked me on bended knee while I was literally packing my suitcases. He figured I was giving him an ultimatum and was threatening to leave him unless he finally broke down and offered to marry him. It was especially odd because we had never spoken about being together in the future, and I had never even introduced him to my family. His proposal was so unexpected and inappropriate, I simply asked him to leave my apartment and promised I’d send him a postcard from Europe. I couldn’t get that door closed behind him fast enough! –LucindaYolanda
34.
We were only dating for six weeks. He also proposed in the middle of sex with no ring, like literally stopped mid-thrust and asked. –Anyanka-goes-rawr
35.
I was 17 in high school, he was 16 in high school. He came to my house one day and I was taking a nap. He just let himself into my house, woke me up (I’m the only personhere) and drops to one knee and pulls out a cheap ring, probably from some kind of coin machine at a mall. My words were “I just want to go to bed.” and he started crying, saying he didn’t want to lose me. I told him to go home. We’d been dating for like a year and continued dating like it didn’t happen. Sometimes I wonder if that was even real, it seems so bizarre. Also, he cheated on me the entire relationship and a few years after we broke up got busted for statutory rape of a minor. So. Good riddance! –blahblahbrandi
h/t: Reddit
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