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Dear Captain,

I had a friend I first met about 15 years ago. We got on amazingly well: mutual friends called us “one mind in two bodies” because our personalities were so similar. We understood each other almost perfectly and could talk and laugh for hours about things nobody else quite got. We then had an extraordinarily intense romantic relationship: we were ridiculously in love and had an incredibly deep connection. It ended because I was super needy and honestly wasn’t ready for that sort of relationship. We were both heartbroken and intended to get back together one day, but life took us in other directions. We tried to stay friends but I wanted too much from him; he felt he had to keep me at arm’s length. I told him I had too many messy feelings to have a healthy friendship, he begged me not to go, I said I hoped to be back one day, there were tears on both sides and we went our separate ways. This was in 2008. Resolving to take something positive from what happened, I worked hard on myself, addressed the co-dependency issues that had driven ALL my previous partners away, and now I’m married to an awesome guy I’ve been with for 10 years.

This January, we finally got back in touch. I apologised for some hurtful things I’d said when I was in a lot of pain over losing him. I told him how I’d changed for the better. I said if he forgave me for being a jerk I would love to rekindle that awesome friendship if he wanted to, now Other Feelings weren’t an issue any more. He replied to say it was a lot to take in (naturally) but he would answer via email, not to worry if that took him a while and, in the meantime, how was I?

Since then we’ve exchanged several messages but often he takes days, even weeks to reply so we haven’t really got a good conversation going (except one night when we texted about random stuff until 2:15am, which showed we still have that great connection and same weird sense of humour). Because communication has been so sporadic, it’s hard to gauge what sort of friendship we might have if at all. When he does reply he’s warm and affectionate, laughs at my jokes and sends me cool stuff he knows I’ll like. But because of our complicated history I’m unsure how well I can walk the line between “yikes, co-dependent ex-girlfriend is messaging too much!” and not having enough contact to re-establish a friendship.

I’m trying to give it time – maybe he’s just not ready and could be navigating A Swamp of Unexpected Feelings himself. But I feel with this sort of situation it’s important to be honest and open from the start about what you want, like I was in my first message to him. I gently reminded him he said he’d email me and while he didn’t have to, I’d appreciate knowing where things stood between us. He said he was busy but could do it next week… which was several weeks ago now and don’t feel I can ask again. Me badgering him when he needed space was why we stopped being close in the first place.

I’m feeling a bit lost about how to handle this situation. At the moment I’m playing it by ear, replying to messages when they come, trying not to send too many back, giving him space when he doesn’t reply. But while I’m thrilled to be back in touch, there’s this elephant in the room, it’s…uncomfortable, and I don’t believe he’s going to send me that email – it’s been nearly 2 months. How can I figure out what the relationship is between us without making him feel pressured to talk about things he clearly doesn’t want to talk about?

Hopeful Friend

PS I searched for similar letters but the closest I found was you advising not to reach out to an ex for friendship until your feelings reached the point of “oh yeah him, I wonder how he’s doing, would be fun to catch up.” Which is what I did… but now I don’t know what to do next.

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