Not me, but my twin brother:

He met his first (and only) girlfriend in middle school at the age of 12. For the next decade and a half, they were inseparable - always glued at the hip. Sometimes it was really cute to see them together and other times it was annoying, but nevertheless it was clear these two were meant for each other.

One day, he comes over my apartment and just wanted to talk. Okay, sure - the beer is in the fridge. Anyway, it was a really awkward exchange and he eventually tells me he plans on proposing to his girlfriend. I congratulate him, tell him they are an amazing couple, and will be very happy together. He doesn't seem so sure but after a while, he snaps out of it and everything is normal. We are both joking together and talking about the proposal. He worked in construction and didn't make a lot of money, but he showed me the ring and he must've saved for years to pay for that thing.

Anyway, three years later, he STILL hasn't proposed and I bring it up casually at a family reunion. He says he always gets too nervous and can't get the words out. I try to pump him up as much as I can and he eventually tells me he will take her to our beach house (30 minute drive) for a romantic evening on the beach and do it THAT NIGHT.

As they are driving there, they are both really quiet and my brother realizes something is up but doesn't really think much of it because he is so nervous about the upcoming proposal. They have a silent night with very little talking which is finally interrupted by his girlfriend bursting into tears. She tells him that she has waited for so many years for some type of progression in their relationship (probably referring to a proposal) and tells him that she thinks it will be best if she moves back home and they stop seeing each other. My brother just sat there in silence with his head in his hands at the table. She starts to collect her stuff and asks why after nearly 17 years of a relationship that he isn't even going to fight for her. He casually holds up his hand with a small black box in it - with the ring in it. She takes one look at it and begins to sob even more. Confused and hysterical, she left my brother there alone for the rest of the night while she drove back to her parent's house.

He was crushed and hasn't been the same since, although he did go on one date about 2.5 years later.