I don't regret any of my break ups (the relationships needed to come to an end) but I do regret dating "John" because we were close friends for like 5 years before we started dating. After two years, I broke off the relationship because even though we loved each other, we weren't in love. A few months later, I met and started dating my current husband. John wanted to get back together, but I was honest and told him I had started dating someone else and I didn't want to be a jerk and string him along. He said okay and I didn't hear from him anymore. Flash forward a few months to a pre-marital counseling session where we discussed our exes. After hearing about John, my husband was like, "Wow he sounds like he was really cool. Maybe the three of us could hang out someday". I dunno. I know they'd hit it off (they share a lot of the same interests and neither have many male friends because they're not originally from this area) but I feel like it'd be weird. The only way i could see ever hanging out is if a lot of time went past, like several years and ex was in a happy, committed relationship and we were hanging out in a group. One of my friends is in a situation similar to mine. She was best friends with a guy for years, they dated, then broke up. She's been in a relationship with another man for about 2 years, but whenever she and current boyfriend drive to her hometown, they hang out with her ex. She talks to her ex regularly and she still calls him her best friend. This summer her ex is going to be studying abroad in Korea, and she and current boyfriend are going to stay with him. Thoughts?