I was married for ten years in a relatively loveless relationship. She and I split up close to four years ago, and the divorce was final about a year ago. A few months back I decided to start dating again, so I joined a few online dating sites, and I went out on a few dates here and there. One of those was with “Mary,” and we hit it off very well. I’ve been seeing her quite a bit, but she and I had an understanding from the beginning that we were just dating and that both of us would probably see other people until we got to the point of wanting to commit (if that would happen at all).
So while dating other people, I met “Sarah,” with whom I also have a lot in common and good chemistry. Sarah and I haven’t been out on as many dates as Mary and I have, but I feel that Sarah and I have more commonalities then Mary and I do. The conundrum: Mary and I have slept together a few times, and, though I really like her and I could definitely see having a long-term relationship with her, I would like to get to know Sarah better before deciding whom to get more serious with.

If I were forced to choose right now, it would be Sarah as I believe we would be a better fit than I would be with Mary. But I feel that, if I continue to see Sarah, I’ll be cheating on Mary, even though Mary maintains the “just dating” status. If I end up saying goodbye to Mary in favor of Sarah before Sarah and I really get to know each other, I may end up losing them both. If Sarah finds out that I’m now being intimate with another woman, more than likely it will be over between us. What do I do? — “Just Dating” Two Women

Aunty Lisa says

The conundrum here isn’t that you’re “just dating” two different women. The problem is that you’re “just” dating one of the women and you’re doing a lot more with the other woman. It’s an unequal playing field. The only way to make it equal is to either stop sleeping with Mary or be honest with Sarah that you’re dating and sleeping with another woman. Since you believe that Sarah, if she knew you were having sex with someone else, likely wouldn’t want to continue dating you (and you’re probably right), it seems like your best bet to continue getting to know both women while also leveling the playing field is to stop sleeping with Mary.

How do you do that exactly now that you’ve opened that part of the relationship? Well, it might be too late. But your only shot is to be honest and say: “Mary, I really like you and I think we could potentially have a long-term relationship, but I’m still dating other women and, since I am a sexually monogamous person, I’ve realized that I need to not sleep with anyone until I know that I’m ready to exclusively date that person.” As I said, it may be too late to make that proclamation and spare hurt feelings — you can imagine that for a woman (or, anyone, really) it would feel like a rejection to start sleeping with someone and have that person tell you the sex needs to stop. But if you lose Mary over being honest with her and trying to respect both women you’re seeing, then you know she wasn’t the one for you. And moving forward, you know about yourself that you can’t start sleeping with someone until you’ve decided you want to date her exclusively.

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