Worst relationship moment:
I had bought an engagement ring, to propose to a girl I had dated for almost 3 years. I was 24, she 23 years old.
While on a saturday day on the town, I had planned to have a dinner with her in a real upscale restaurant, and pop the question right after the main course, so that either the dessert would be comfort food or a celebratory piece of cake.
Somewhere, between appetizer and dessert, she dumbed me. I was declared to be on the friends zone, that it was all over between us and that I could come collect some of my stuff from her place in the next week.
This came pretty much like a lightning from a blue sky. We had talked of going for an international vacation in a few months, and even selected a destination. We'd met eachothers parents. We pretty much spent every weekend together, and saw eachother often during the weeks despite living almost 20km apart.
Fast forward two weeks, and I see her out on the town with my best friend, apparently having the time of their life.
So I wrote her a letter, wishing her a happy life in it as sincerily as I could with my heart of the gutter, and added a copy of both the proof of purchase with the date underlined and receipt for returning the engagement ring to the shop. When she tried to call, I didn't answer. She didn't call again, and frankly I was happy that way. If she was sincere in leaving me, an engagement would have been a colossal mistake. And if she did that in the name of some kind of powerplay, or in an attempt to make me jealous, then she wasn't the girl I wanted to spend the rest of my life with anyways.
My former best friend... let's just say I didn't keep in contact, and he didn't bother to either.
Happier moments: well, when a girlfriend later on decided to repay me for being a driver and pack-mule for her and her friends on a whole day of shopping - in a clothes exchange booth that had thick walls and proper doors...But even better was a picnic with the same girl on a fjord cliffside in Norway, watching a sunset. Seriously, the fjords are amazing.