Is there a future with my ex?

My ex and I dated for two years before breaking up. I was devastated. I knew he was the one – and he was the only real love I'd ever experienced. He had some deep-rooted emotional issues to work out on his own. We both experienced a lot soon after the breakup, traumatic deaths in both of our families, which briefly brought us back together, then it was done again.

Flash forward five years with no communication and boom – there he is. Reflecting, showing empathy, and opening up like he never did before. It’s been nice to hear from him, but it has also brought back some (good) feelings. We have both had relationships since the breakup that have not worked out. He also has a couple of kids now. I’m writing because, if the opportunity presents itself after some time, I would like to see if something is still there. I guess I don't know if I should be open to that, considering the past emotional roller coaster, but at the same time, it seems so different now. I could very well be getting ahead of myself, but it's kind of nice to think about. Is there a future with someone who has children with other people? Is the whole "if you love something set them free; if they come back, they're yours" statement true?

– Case of the ex


"Is there a future with someone who has children with other people?"

It's very possible. It might be a different kind of future than you imagined. It would require empathy and communication, and you'd have to be open to spending time with someone who needs to prioritize others. But of course there could be a future with this person. It's worth learning more about him and his life to see if it interests you.

"Is the whole "if you love something set them free; if they come back, they're yours" statement true?"

Eh, I don't know about this one. Maybe? As we've learned from recent letter writers, some people get "set free" and then show up once a year with ambiguous texts or Facebook likes. Passive communication is so easy these days, and it doesn't always turn into anything. But in your case, you can pay attention to how it grows. It's too early to know what all of this means.

Something to consider: If you know you're developing feelings for this person again, you may want to bring them up sooner than later. We've had a lot of letters from people who spend months – sometimes years – wishing and hoping for a person to want them, only to find out that it's not going to happen. If you know you want to try for more, let him know.

– Meredith

Readers? What's possible here?