We had a mutual break up after a few months and remained close afterwards. In college, my now wife and I decided to take our friendship to the next level. We were married a few years later and now have two kids.
There is no awkwardness between any of us and the three of us frequently go out to dinner together.
Everyone is lighthearted about it and my wife makes jokes all the time. My sister-in-law is now married So, yeah, that worked out.
My current SO significant other and I were very close friends in high school and we would always set each other up with dates and stuff. She set me up with her younger sister and things were going great until she cheated on me. We broke up, and my SO was on my side of the whole thing and completely supportive. I was shocked to learn that she had feelings for me since second year college. It was definitely weird at first and my family would often crack jokes about it.
We have been together for eight Dating friends girlfriends sisters now, married for 2.
One thing led to another and six months later here we are. My Dating friends girlfriends sisters has been dating an ex of mine for the last two years, and the ex has plans to propose to her at the end of the year. However, she adored my family, so she continued to hang around with them - parents, brothers, etc.
Fast forward another year or two, and they get married, so now my ex girlfriend is my sister-in-law Friend turns out to be a big asshole, me and the sister start dating.