Dating Two Women At Once

Wednesday | April 20, 2016

Love Letters Dating

Dating Two Women At Once

I’m having trouble choosing between two women. Let me give you a little back story first: I was married for 10 years, and it was a relatively loveless relationship. We split up about four years ago. The relationship was long dead but it was still very hard for me to make the decision to start dating again because I took my marital vows very seriously.

A few months back, I decided to start dating again. I joined a few online dating sites and went out on a few dates here and there. One was with “M.” We hit it off and had chemistry. I’ve been seeing her quite a bit since, but she and I have had an understanding from the beginning that we were just dating and both would probably see other people until we got to the point of wanting to commit, if that happened at all. So while dating other people, I met another very nice woman – we’ll call her “S.” S and I haven’t been out on as many dates as M and I have, but I feel that S and I have more in common than I do with M. Both women have great qualities, I’m attracted to both of them, and both of them started off with the understanding that we were just dating.

Here’s the conundrum: M and I have started to get physical and have slept together a few times. I really like her and I could definitely see having a long-term relationship with her, but I feel I haven’t given S as much of a chance. The other problem is that if I was forced to choose right now, it would be S, as I believe we would be a better fit then I would be with M. But S and I haven’t had enough time to really get to know each other. So now I don’t know what to do. I really like both of them, but I always consider myself to be a monogamous man and feel that if I continue to see S, I’d be cheating on M, even though M continues to say that we’re just dating. If I end up saying goodbye to M in favor of S before S and I really get to know each other, I may end up losing them both. If S finds out that I’m now being intimate with another woman, more than likely it would be over between us.

– What do I do?

I just realized we’re dealing with S and M. OK then.

I’m tempted to tell you that you should continue things with M while you get to know S, but you sound so stressed about the overlap that I think it’s time to make a decision. Some people can date around and make decisions over a long stretch of time, but you are uncomfortable with this much multitasking. It was fine when you were on get-to-know-you dates, but once things got physical, you became uncomfortable.

I can’t promise that S is the woman of your dreams, but here’s the thing – you hope that she is. You mention twice in your letter that you prefer her to M in important ways. It’s clear that you’d like to get to know her without distractions.

Let M go and focus on S. Again, there are no guarantees with S, but you have to take a risk and go with your gut.

– Meredith

Readers? S? M? Both for now?

Dating

Featured Comment

why not just have a conversation with S and see what she’s looking for in this relationship? Does she want something more serious? Does she want to be exclusive? If you’re going to make decisions between two women, it might help to get out of your head and have conversations to find out what they want, but specifically S since you see something more lasting with her. Find out if she’s on the same page.

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