I have a friend I’ve known for 21 years. I met him at uni when I was 17 and he was 18, we’re now 38 and 39.
When I first met him, I really liked him but was painfully shy, so I never said anything. We spent time together doing classwork, chatting in the library, exchanged numbers… but nothing came of it. He soon met someone who became pregnant, and we lost contact for a while.
When he was 20, he got back in touch, he and his partner had split up. We met up, kissed, dated a little. I was still shy, and at that age I didn’t feel ready for a relationship with someone who already had a child, so I held back. Things fizzled out.
A couple of years later, we reconnected again, same story. We dated, kissed, spent time together, but neither of us expressed deep feelings, even though I was secretly crazy about him.
There were a few times when we would bump into each other on nights out and would end up back at his parents house - but we just talked, and kissed and he would drive me home in the morning. I always knew how much I liked him and I think thats why i never slept with him, i was so scared he would break my heart.
Then he met someone else, had another baby, and our contact became very occasional, always platonic. After that relationship failed he contacted me again and we had a night together - we didnt sleep together but it was a great night, i dont remember who stopped contacting but either way - it fizzled out again.
I later met someone myself and was in a 14 year relationship, and he also settled down. Over all of the years we stayed in touch via Facebook messages and texts, purely friendly, chatting about life, kids, relationships, offering advice, wishing each other well.
My marriage has recently ended (not my choice). His long-term relationship has also ended (not his choice) they were together for over 10 years and have a 1-year-old.
Since we’re both single, we’ve been talking a lot more than usual. There’s been some gentle flirting and talk of meeting up. He has three children (21, 17, and 1) with three different women. I have two children (10 and 8 with my soon to be ex husband). Our lives are complicated.
I don’t know if I’m kidding myself that something could happen after all this time. He hasn’t said he wants a relationship, but he often talks about “what could have been” and wonders what might have happened if things had gone differently.
I do like him, I’ve always liked him, but I also know we’re both coming out of major breakups and have a lot going on. I'm in no rush for anything. I'm not interested in filling a void, im not interested in being a rebound either. But I also know that there have been quite a few missed opportunities over the years and I don't want to waste another 20 years wishing I had told him how I felt.
Has anyone else been in a similar situation where a long term friendship turned into something more after years apart? Did it work out?