I’m a man currently in separate relationships with two different women. I love both of them. Neither of them knows about each other and each would be devastated if they discovered that I was in another relationship. As a monogamous man, eventually I’ll have to choose one of them to pursue long-term. Each woman has their pros and cons. How do I choose between them?


Adapted from a personal conversation. 22 Mar. 2019.

Ethical Issues

Before we talk about how to decide which to choose, we’ll have to broach the bigger problem: you’re behaving selfishly and practicing non-monogamy unethically. The key giveaway: you know that the women would be “devastated” if they discovered the truth and so you’re effectively misleading them each moment you don’t tell them. This is a lie by omission. As the person who has information that the others need in order to make fully informed decisions about the future of your relationships together, it’s your responsibility to tell them.

One might attempt to argue that this isn’t a permanent state of affairs, therefore you can wait until conditions change. As soon as you choose one of them, then you breakup with the other and the problem solves itself. There is no other relationship in the present moment that you need to admit to. However, this presents two more ethical problems:

1. The woman you will be breaking up with will want to know why. From her perspective, she’s in a perfectly loving relationship. While you’re off making your decision and choosing the other woman, this woman is under the illusion that her relationship with you still has a future. When you come to break up with this woman, she’ll be blindsided and ask what’s wrong. What do you say? You then have the choice of lying to her—maybe you tell her that you met another woman—but then you’re still behaving unethically. Or you could refuse to justify yourself, which is your right, but you would still have to live with the fact that you mislead that woman for a long time and never reconciled the truth with her.

2. The woman you choose will have had no idea that another woman ever existed. Sure, you’ve solved the ethical dilemma of the moment, but you’ve still committed a sin against your current partner. In effect, you started your relationship based on a lie. She’ll think she knows you as a certain kind of person, but you have a significant part of your life—an entirely different woman that you were dating concurrently and loved enough to stress over—that you’re not revealing to her. You’ll always have to hide that part of you.

This second problem touches upon a deeper point about openness and honesty within a relationship and why they’re such important concepts. If you want to fall in love deeply, then you must open yourself up to vulnerability. You cannot trust a person to love you for you if you fake who you are, and lying about or omitting important facts that would otherwise reveal your personality means that your partner doesn’t love you—they love the persona that you’ve created for them. Aside from the ethics, you’ll have to deal with the negative emotional repercussions. Can you ever trust that you’ll always be loved by your partner if you refuse to open yourself up them, knowing they might discover your secrets and think differently about you? Can you live your life with someone knowing that there are certain subjects you’ll have to be forever on-guard about, having to maintain two different stories in your head: the truth and the lie you tell your partner?

Your partner deserves to know the truth about you. They deserve to know your true personality. And you deserve the kind of person who will love you when you show yourself unreservedly, nakedly, wholly to them.

When To Tell

Now that we know we have an ethical problem, how do we solve it? First, let’s think about how we should have dealt with the problem in the ideal case so that we can prepare for the future, if we ever have the good/bad luck of falling in love with two people at once again.

Ideally, the best time to tell a partner pertinent information is as soon as possible. It’s okay to spend a little time to sort through ethical problems the first time we encounter them in a relationship—no person should ever be expected to have all the answers to life’s quandaries all the time. But you should know enough to reach the decision to tell them fairly quickly.

It’s also okay to spend a little extra time figuring out the best way and time to tell them. Obviously it would be inappropriate to blurt out the truth as soon as you see them—though that would still be an improvement over not telling them—or in some other setting such as a public engagement where they might suffer embarrassment. As long as you’re not stalling because you can’t handle the emotional stress of telling them, it’s fine to wait until the subject becomes relevant. The easiest way to do this is to simply create the relevance: tell your partner that you have something serious you need to talk about, reassure them that you love them, and allow them to set up a time to talk. They can then choose a time that’s appropriate for them.

That’s all well and good for the ideal scenario, but the real question now is about when to tell especially that you must reveal that you’ve already mislead your partners for some time. But actually, the answer is the same: tell them as soon as possible. Come clean, let them know that you only recently came to terms with the ethics of the situation, and then be prepared to empathize with their emotions and deal with the repercussions of your behavior. Because really the only alternative is to continue lying to them. The longer it goes on, the larger the lie becomes, the deeper the ethical hole you’ll be digging for yourself, and the more your partners will be upset if they ever do find out. From a purely pragmatic or hedonistic standpoint, this is about minimizing damage and pain. It’s never too late to atone.

How To Choose

Finally, we can talk about how to choose between two women.

Considering that I tend to focus on non-monogamous relationships, I should at least address this. First, I am not an advocate for non-monogamy. I believe people should be informed of the ways non-monogamous relationships work and they should decide on their own if non-monogamy is right for them. In this particular case, you’re already in a non-monogamous structure, but by accident. So this is a good opportunity to ask yourself if you want to return to monogamy, or if you might consider pursuing non-monogamy (albeit ethically, going forward) since you’ve already experienced a bit of what it’s like. It should be noted, though, that the likelihood is very low of maintaining these relationships as they are—which were started under monogamous pretenses—within a new non-monogamous framework. You’d probably have to start over with new partners, if that’s the path that you choose.

Most likely, you’ll want to continue down a path that leads to monogamy, so how do you choose between two women that you love? There are pros and cons of each. Each you love, but you love differently. You can see two different futures unfold, but you don’t know which will be best. And there’s a third, looming option: what if you’re more interested in the idea of a relationship in general than you are of being in a relationship with these particular women (or if your hidden desire at least confounds your decision-making ability)?

I once knew a man who chose between women by making an Excel spreadsheet of pros and cons and counting them up. It actually worked out quite well for him. That’s the logical path and is an option for a peculiar kind of person (which you may be). But then, when it comes to relationships, I’m much more of an emotional person. So to me, that kind of logic implies that the connection with a particular woman is less important to you than what benefits the woman provides. It would be difficult to tell a person, “I chose to love you because I sat down and thought real hard about whether we’re a good fit for where I want to be in life, and decided we are.” Though, again, there is a peculiar kind of person who would enjoy hearing that. To each their own.

To me, the decision should be emotional. Ask your emotions, “Is this person good for me? Do they naturally make me feel love for them? Do I feel loved by them? Do I believe that love will grow?” Hopefully, you’ll be able to tell a person, “I love you not because I thought long and hard about it, but simply because I am compelled to love you. It’s inexplicable, indescribable; it simply is.”

But then what if you’re able to feel that (or even think the logical case) about both women, neither more than the other? Well then I’d argue that you truly are non-monogamous, at least for the moment, and should expect to be in this space until some external force pushes you to choose one over the other. You might as well internalize it and live with it (ethically, by fully informing both partners), and read more of the material on this blog to figure out how it works.

This approach also allows you one very interesting option, and would probably be the one I’d choose if I was in your position: if you’re dating two women who expect monogamy, then tell them exactly what you’re thinking and let them choose for you. In other words, if we’re all following the ethics of full openness and honesty, then your partners deserve to know that you’re facing this kind of dilemma. If they knew your thought process, then it might force them to consider what kind of life they want with you. And if they’re making that decision, then it would only be fair if they also had the freedom to date other partners in order to determine what might work best for them.

That way, at least everyone is on the same page and is behaving fairly in regards to each other. Your partners may simply cut off the relationship, knowing that you’re facing this dilemma, or because they intrinsically disagree with non-monogamy. They might choose other partners instead of you (perhaps both of them, leaving you alone). They might decide for themselves that non-monogamy is pretty great, and this is a good foothold onto a new phase of life.

Whatever comes, you must be emotionally prepared for it. It’s nobody’s fault that you fell in love with two women at once—it’s a blessing that you found something twice that’s so hard to find even once, and it’s also a new and difficult challenge. That’s life. Instead of avoiding it, you might as well dive directly into it, take your punches, learn your lessons, open yourself up to vulnerability, and grow as a person. You’ll come out stronger in the end.

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