Has anyone ever dated anyone years after breaking up, and does it tend to end badly if so?
This isn't someone I dated as an adult, we were teenagers and dated for two years. Break up was devastating to me as a teen (first relationship) but we stayed in contact on and off over about 15 years. Particularly if one of us has a really bad time we reach out and connect because we get each other in a way others don't, the couple of years we spent together were very significant for us both. We supported each other through some really difficult stuff.
Anyway, we are both currently single at the same time. I think I was probably always the one that got away for him. I feel as though situations like this might be likely to end badly? But I'm not sure if the fact we were so young mitigates it a bit, in that it's not like one of us had an awful personality trait or was abusive and the other managed to escape. We both had difficult lives and it was the wrong time then. I guess I'm not sure if it's mad to think that the same person years later could be worth a shot?