I used to have a friend that turned into a friend with benefits and we would hang out/hook up a couple of times a month. We’d sometimes see each other at group events also, and had a bunch of mutual friends. I valued him as a friend above anything we did physically. We eventually stopped hooking up and I started dating someone. I haven’t seen him in a year and a half, but every couple of months we’ve texted each other, and once or twice emailed each other. I’d really like to see him and catch up with how things are with him, but I have a boyfriend and I’m not interested in anything romantic or physical with him.
So my question is: How should I go about asking if he wants to meet up? For a drink or something. Will he think it’s weird that I want to hang out if I have a boyfriend? I really just miss him as a friend. Should I not even bother? It just seems a bit crazy that two people who used to be good friends can’t catch up, just because there used to be something physical between them.
LemonVibe 
[Do you know how your boyfriend would feel about you hanging out with a former long term FWB? I’m not saying he should tell you whether or not you’re “allowed” to go, but it seems like a dangerous situation. If you really want to hang out with this friend, I suggest starting out with something like lunch, or another situation during broad daylight with no alcohol involved.
[Ugh, why? I’ve lost touch with plenty of friends over the years. Why is it so important just to catch up with him once?
I mean, if you really want to know what’s going on, why not friend him on Facebook or something? I’ve started to realize that I have several levels of connections on Facebook. On one end are the people whom I know casually and whose lives I am superficially interested in keeping up with. Would I ever make the effort to physically hang out with them? Doubtful. Would I be sad if I lost touch with them forever? Meh… probably not. But I’d definitely wonder what they were doing from time to time.
Why not make this guy one of these connections? I mean, you obviously don’t intend to become good friends. Just let it go. The potential awkwardness is, in my opinion, not worth the one-shot hangout.
[I get the idea. A part of me misses some exes for strictly friendship reasons. Doesn’t make it appropriate for me to go see them. I agree with what Ms. Roosevelt said, how does your boyfriend feel? I’m guessing this won’t be one of those things where everybody is cool with it.
[I had a similar situation. Had a FWB for about a year until I met my boyfriend. Then the FWB and I pretty much lost touch completely. I miss the fun we used to have, sure.
But.
I’m not sure he and I should ever hang out again. I mean, with a group of people or at a party, fine, but he and I, one on one, to catch up or “hang out”, I just don’t think much good will come from that. Not because I still have feelings for him or anything, I just don’t think my boyfriend would like the idea much, and I don’t miss my friend so much that I’ll ever be disappointed we can’t be friends again.
Sometimes, you have friends for a while, and then they’re out of your life. There’s lots of reasons. For you, the reason was that you met your boyfriend and didn’t need the relationship you had with your FWB anymore. Be happy with your boyfriend. Email or text your friend to keep in touch. Say hay on Facebook. Invite him to group events. But I can’t advise that you try and start up your friendship again. It’ll probably make your boyfriend insecure and that’s not what you want if you really love him.
[I agree with what’s already been said. There’s really no reason to get together one on one. It’s only going to be awkward.
If you really miss him as a friend, then be social with him in a group situation, but don’t let yourself be alone with him (especially when there’s alcohol involved). If you really are friends, then that will be enough for a while. If not, you’ll realize it.
You love your boyfriend, and that’s a little bit of a trust violation, no matter how you look at it.
[Just don’t do it. If I were your boyfriend, it would bug me whether you say that it’s innocent or not. It also seems a little odd that you are more focused on how the former FWB would feel about you wanting to meet up with him rather than how your current boyfriend would feel about it.
[If you truly value your relationship, just catch up over facebook chat. You might intend for it to be a one-time innocent meet up, but there’s just too much potential to damage your relationship. Your boyfriend may not be able to see your intentions as clearly as you can, and it’s only respectful for you to tell him that you used to have sex with this guy if you’re intending on seeing him again.
[I guess I don’t understand why everyone is so against the idea of you sitting down and talking with him (that is all it would be, right?). There’s a reason that those people are your past whether it be exes or former FWB. Just because you were sleeping with them before doesn’t mean that you’re going to do so again! I know that any time I’ve met one of my exes, I’ve never wanted to put myself in that pot again. I’m still very good friends with my ex-wife, but I’d never go back to her. Sometimes you just realize that you were always better off as friends.
But, for the love of Gouda, DON’T sit down with him for drinks and such! I agree with everyone else in that regard. A social setting, like a lunch date with friends would give you a chance to catch up without putting yourself in any risk of making a mistake due to unseen circumstance.
As far as your BF is concerned… well, that’s tricky. Any way you look at it, if you really want to meet up with this guy, I think your BF deserves to know the history of it. It’ll make him uncomfortable, but this way you’re laying it all out on the table for him. You’re letting him know that your interest in this other guy is purely friendship based. It’s the give and take of trust. You’re trusting him with the knowledge of your past and he’s trusting you to keep it in the past. When I first started dating my GF, she’d go hang out with the guy she was dating before me every now and then. I didn’t like it, but I don’t own her and trusted her to want to be with me. That trust paid off because not only have we been together for 5 years now, but after seeing him, she’d tell me how things went and even told me of the time he tried to pull some shady stuff (needless to say, SHE didn’t want to hang out with him after that). I trusted her and so she knew she could trust me as well. I’m not saying your BF is going to like it. He may not even want it to happen, but you at least deserve to let him know what the history is before you meet up with this guy.
As far as how to go about setting you former FWB’s mind at ease, just tell him. You two were close enough at one point in time, you shouldn’t have any problems just laying it all out there. Explicitly mention that you don’t want anything physical. If it’s friendship you’re after, there shouldn’t be any confusion about it.
But before you get to that point, talk it over with your BF.
[Based on your follow up post where you said that you didn’t want to be friends again, I don’t understand why you can’t find out all that information by just chatting and emailing him like you usually have. The pieces of information where you say, “I valued him as a friend above anything we did physically” and yet, “I don’t really want to start up our friendship again” and yet, “I’d like to go out for drinks and catch up” confuse me.
This is coming from your friend’s potential perspective but I usually don’t hang out with people who don’t want to see me again afterwards (i.e. be actual friends.) But that’s just me.
[Don’t meet up with him. Nothing good can ever come from introducing an ex into your current relationship (or any future relationship). C’mon sister… FOCUS!