5.

This sad situation:

“A more gay, funnier, and subverted side to this story, but I did a sort of non-traditional proposal to an ex-girlfriend of mine when I was in my mid-20s, because she loved surprises and I REALLY wanted to surprise her with this. She got all flustered and scared, because her family was all homophobic conservatives and she never did end up telling them that she was dating a girl (I have a pretty masculine name) and she was worried about me because she didn’t want me to get insulted or hurt by her family.

It ended with her trying to think up the best hypothetical ways to tell her family that she was ‘marrying a girl’ with the least awful result because she didn’t want to reject me since she really did love the idea of us being married, and me telling her that if she wasn’t ready to marry because of whatever reason then she can say no. It ended with us not being engaged that day.”

u/EntertainmentAny763

Source: https://www.buzzfeed.com/ryanschocket2/rejected-engagement-proposals-reddit