“Am I Cheating on the Women I’m Dating?”


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

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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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. I don’t see that big of a problem, you don’t like Mary that much, and are just stringer her along in case something better comes a long, now that something better has come along you don’t know if something better likes you as much as you like her so you still want to keep Mary as a safety net. Just dump Mary, and take a chance with Sarah, and if it doesn’t work out start all over again.

    1. Avatar photo muchachaenlaventana says:

      yes, this exactly.

    2. Avatar photo Addie Pray says:

      Yes, what Bagge and Wendy said. Also, hi everybody! I’d just like to say I walked to work today without a coat. IT’S SUMMER, BASICALLY! REJOICE!

  2. Monkeysmommy says:

    Christ on a cracker… You really couldn’t figure it out that you should stop boinking Mary if you want to “just date” both women? Does Sarah know you are dating Mary? Honestly, it doesn’t sound like there even IS a choice, if Mary maintains she wants to “just date”…. I swear, it sounds like you just wanted a pass to keep having your cake and eating it too.

  3. I was recently in a relationship like this. It’s better to let Mary go and find someone that is looking for the same things as her, not drag her on like you are.

    Maybe you should stop dating for a hot minute and reflect on what you want. “Settling” or “Leading someone on” usually stems from other issues.

  4. dinoceros says:

    I feel like there’s a lot of unnecessary drama here. If you’re not exclusive with someone, then it’s OK to see other people. But the truth is, casual dating has an expiration date. You’ve reached the point where at least one of them is not going to be interested in continuing seeing you based on the way things are. You do need to be honest with them so they can make a decision based on the current situation. The options are trying to see them both and telling them, which means you may lose one or either… or selecting one and dumping the other. This is the standard process of casual dating — it can’t go on forever.

  5. fairhairedchild says:

    LW, Wendy is right on all accounts, especially about learning what you are and aren’t ok with for future relationships.

    I can empathize with this LW because I was in a similar situation where I had a person that I was sexually exclusive with, but I also was able to date, and if the dating lead to wanting to have sex, I had to notify and break it off with the FWB first. After a while of the casually dating some people, but exclusive sex with a different person, I figured out that I couldn’t do that because it felt like cheating to me still – even if I was given “permission” to see other people.

    I even told the one guy I had casually been dating that I had someone I was exclusive with for sex and he was ok with it and told me he was dating other women too so it didn’t bother him. That made me feel even MORE indecisive about going ‘the next step’ with him.

    In the end I broke it off with everyone, and found that I can’t do the open relationship/FWB style because it felt too much like cheating for me when seeing anyone outside of the sexually exclusive relationship. I also felt like it really held me back from “trying” to really find out if I was compatible or not with someone I was casually dating because I had that “fall back” person I would see and get sexual benefits as well.

    So break it off with Mary, or at least be up front with her that you need to cool it so that you can be more focused on a different relationship that you don’t want to screw up if she finds out that you are also casually dating, and sleeping with, someone else.

    1. I just went through this exact thing! We should be friends.

  6. Anonymous says:

    No you’re not cheating. You entered the relationship with Mary as a polyamorous relationship with the possibility for monogamy. Since ye have not become monogamous you are not cheating on Mary. Next thing is are you being honest with Sarah. Did you tell Sarah about Mary and enter the relationship with Sarah as a polyamorous relationship. If not you’re not being honest and you’ve messed up. You also need to keep bringing up the fact that it’s a polyamorous relationship with Mary if you want to continue it. By the sounds of it you are holding onto the idea of being monogamous with Mary out of fear not affection. If you can’t handle being polyamorous you should end it. If she can’t handle it you should end it. Next you need to be honest with Sarah. Find out what u want and go from there. Lastly don’t be a little b***h and face your problems head on don’t beat around the bush because it’s awkward for you.

    1. dinoceros says:

      I don’t think this is polyamory so much as how people are typically not exclusive when they first start seeing someone and often date several people prior to becoming serious with one.

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