Ok, so. “Mike” and I have been dating for about six months. Not exclusive, but I don’t think he’s dating anyone else, at least not nearly as seriously as me. When we had the exclusivity talk, he said he wasn’t looking for meaningless sex, but he wasn’t looking for a relationship, and he definitely wasn’t looking for monogamy (but he also admitted that wants and needs can change over time). I don’t know about his previous love life too much, but I know he spent his 20s in LTRs with strong-willed women, one of whom he lived with, two of whom left him for women, one of whom cheated on him….with the woman. I think he doesn’t want to feel tied down, or like someone’s keeping tabs on him. He likes his space and his time and can only handle people for so long, kind of like me. I want to find out why he feels the way he feels about relationships, but that’s an issue for another time.

When we’re together, he’s super boyfriendy. Hand-holding, cuddling, forehead kisses, all of that. I know it’s likely more habitual than anything, and I’ve pointed this out to him (because it’s kind of in opposition to what he claims to be looking for), so I’m not delusional about this. This question isn’t about whether you think he’s into me or whatever. I’m pretty level-headed about all this. I mean, six months is enough to know or not, you know? (No, but seriously, you’d be proud of me for handling my shit on this one.)

In the fall, I was dating other people—a lot of other people—but we never discussed any of it because I didn’t think we were going anywhere, and it was the early stages of everything, so who gives a shit? You assume the people you’re just starting to date are dating other people until you have an explicit discussion about it. So from then on, we’ve just kind of had an open thing going, not labeled, but more than casual. We text during the week; there are emoticons used. He’s really sweet, and easily the most emotionally mature man I’ve ever dated (except for the whole wanting to prolong relationship limbo indefinitely thing, which brings me to…)

So, I deactivated my OKCupid account, not for Mike, but because everyone else was awful and I’m happier when I’m not on it. Except this one guy wasn’t totally horrendous. We went out last weekend. We had a good date, he lives in my neighborhood, great guy. We’re going out again at some point next week. I don’t get the feeling that he’s approaching things the same way Mike is, so I don’t think he’s dating multiple people at the same time, etc. etc. Of course, I don’t know this until we talk, but it’s only date two. Is that too soon to talk about that? Should I mention that I’m dating someone already? I feel like I have an obligation to this new guy to tell him, since it’s been six months with Mike, and it’s a “thing”.

And then there’s Mike. We haven’t talked about this in a long time. We haven’t had an updated state of the situation or whatever yet, and I think it’s time. Not to be all “where is this going because if it’s not going X, then I’m done,” but more like “Ok, so this is still what’s going on, right? We cool?” I assume he still doesn’t want to be monogamous, which again, is fine with me because it goes both ways, but do I have to disclose that I’m dating other people? Especially since I feel it necessary to disclose it to the other people? I feel like, yes to a certain degree. It doesn’t mean I want to lock it down, or label anything, but I feel like continuing the way we’re going, which is basically inside a vacuum, is going to end in disaster. But I also feel like having this discussion acknowledges that we care about each other, and that our situation is more involved than originally planned. And I don’t want to scare Mike away, because we’re really great together, and I’m totally fine doing this gray area thing and seeing other people until he figures his shit out. I’m up for keeping it open, as long as we both agree to be open and honest with the other people we date (and maybe just not tell each other about our exploits, but those are details to be ironed out later)… but wouldn’t that sort of mean we’re in an open relationship?

I asked a friend of mine who’s in an open marriage about this also, so I’m waiting to see what he has to say, but I’m curious about everyone else’s take on this. I’m just trying to navigate this so I can avoid unintentionally hurting anyone’s feelings, including mine.