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.

Hello, Hopeful Friend,

What if “having a pleasant conversation now and again” is “the situation” with this friend? What if this is the good part, right now, where you’ve changed and let him go and made this whole happy life without him, and he’s made a whole happy life without you, and now you both know that, and you had a pleasant time catching up a bit, and that is better than the 12-year silence you had, that’s the win.

You used to chase him and he used to run away.

Then you didn’t speak for 12 years.

Now you’re back in touch and you’re already at “Per my last email, what is our ENTIRE DEAL?” levels of investment and it sounds like he is…not. i.e. THAT is the deal with your friendship.

Answering “Would you like to be friends again?” with “That’s a lot to take in…” and waiting weeks between communications is not a signal that says “Fuck yes, old friend, let’s dive IN.” He’s glad you’re happy now. He was glad to catch up a bit. He’s maybe testing the waters a little by sending the odd meme or joke – “Can we do this? Can Hopeful Friend be cool? Do I actually want to reconnect?” – But the friendship is probably not going to become the huge, important, dramatic connection it was in the past, and if you chase him again he will run away again.

Prescription:

Do something nice for yourself to celebrate how far you’ve come in 15 years.

Every time you start feeling anxious about this friendship, do something nice with friends who do not leave you hanging, friends where you know where you stand, friends who don’t have this fraught history, friends who are not exes. Also, do something nice for and with your excellent spouse. You have people in your life who don’t make you feel like you are chasing them, who don’t leave you hanging. Celebrate and appreciate them. Put your energy there instead of into re-forging this old connection.

Assume your friend is not going to send that email. Live your happy, functional, much -better-after-15-years life like he never will. If you find yourself obsessing or getting very anxious and overly-invested in this, check in with your mental health team for support.

Texting with exes late into the night is not a reliable recipe for getting over them. GENERAL ANNOUNCEMENT. “Oh, I’m married, I just want to be friends!” I believe you! And yet, texting with exes late into the night is not a reliable recipe for getting over them.

Do not “just follow up” or otherwise contact this guy. Do not chase him. Do not seek to define this. If he wants to be friends? He knows where to find you. He has choices.

But also? Don’t beat yourself up for getting excited, or for feeling your feelings about being back in touch. He was truly important to you. Having him acknowledge how much you’ve changed would probably feel pretty great, as would having this great friendship again. It’s probably not going to go like that, but it doesn’t make you silly for wanting it or for hoping.

“He’s not that into being friends anymore, I need more from friends” is an okay need to have, an okay thing to decide if he doesn’t ever get back in touch, or does so only sporadically. “I’m glad to have re-connected but this person still makes me feel a lot of anxiety” is an okay thing to decide. It doesn’t have to come out in ultimatums, nor does it mean you failed or that anyone is bad, or that the good things you shared weren’t real and important. It does probably pay to remember that you parted ways for a reason, and even though you did a lot of work on yourself since, “restored friendship alliances” are not the automatic prize for that. You get to show you’ve changed by showing that you’ve changed and then living the life that you’ve changed for yourself. That’s success whether this old friend stays in your life or not.

Let go, remove pressure, and don’t do work for people who are not working at being good to you. You’ve already done so many hard things to reshape your life into its best one, I’m confident that you can do one more. ❤