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What Happens When You Try To Date Two Women At Once?

I’m no stranger to the idea of having two girlfriends. When I was a teenager, I often refused to commit myself to a single woman, preferring instead to keep my options open. There are definitely advantages and disadvantages, but usually (in my experience) there are more problems created than problems solved by this type of arrangement.

As a bit of a disclaimer, I do not think that anyone should ever be dishonest with the person they’re dating. If you’re not being exclusive, I beg you to not let any of the women you’re involved with think that you are. It’s not only hurtful, but it can cause its own subset of problems. For the purposes of this article, I am going to assume that the women you’re involved with know about each other – because they should.

This also applies to the idea of dating a man and a woman simultaneously (for my bisexual ladies). It may work for some people, but here are a few reasons it doesn’t really work for me.

There will be jealousy.

If there is any part of the relationship that involves deeper feelings than just sex, there is going to be jealousy from one of the partners. Even sometimes if there’s only sex, someone is going to get their feelings hurt, and there’s not a lot you can do about that.

Some women might not feel jealous of other women, and I applaud you. We shouldn’t really feel jealous of each other, because from a fundamental standpoint, we are all equal. But just because we “should be” equal doesn’t mean that jealousy can be kept away that easily.

If you’re trying to date more than one person at a time, you’ll have to anticipate at least one of those people being jealous about the situation. This even extends to “committed open relationships”; even if we do not “allow” ourselves to feel jealous, the part of the brain that controls this particular emotion is not easily shut off.

There will be confusion.

At some point in time, there’s going to be the question of which person means more to you. Whether this is because of one of the women giving you an ultimatum, or it’s a result of your heart becoming attached to one (or both) of them, this confusion is likely to cause pain – not only for you, but also for your partners. This can even be true for the one you “choose” in this situation.

Even if you keep the confusion to yourself, there will likely be a question in the mind of the people you’re dating as to who you feel more attracted to, more attached to, more turned on by… Well, you get the picture.

This confusion isn’t necessarily a bad thing, as it’s important that we question our motives when it comes to life, love, and everything else. But if your confusion begins to take over, you might have to take a step back from both women – which will likely cause even more pain.

There will be competition.

A little competition is healthy in life. It motivates us to do better, to be better, and to aim higher. But if the women you’re seeing are too competitive in respect to each other, this can be dangerous. Sometimes this competition will result in someone feeling inferior, or someone getting seriously hurt (like physically hurt – some women can get violent when they’re jealous!).

Of course, this competition and jealousy can lead to even more confusion. After all, it’s hard to quantify our emotions, and just because we know someone is the “better” choice doesn’t mean that’s the person we’re going to pick. We might end up settling, in one way or another.

There will be a back-up plan.

This sounds like a good idea, sure. As someone with occasional severe anxiety, the idea of having a Plan B is hugely reassuring. But a quick look from the other side of things can show just how dangerous this “back-up plan” thing really is. After all, how would you feel to know that you were someone’s back-up plan? Chances are, this is how your back-up plan will feel – and she might reject your offer to be second choice.

No woman wants to feel like a booby prize, or at least not any woman with self-respect and self-confidence. Being a runner up is no fun for her, especially if you are that person’s first choice.

There will be doubts.

When and if you do choose one of these women, there will always be the question in her mind as to whether she was the first choice or the second choice – and that can make the exclusivity more difficult once it comes up. We would like to think that, once we make a choice, we’ll be confident in it – but that’s not always the case.

You’ll doubt yourself, too. You’ll wonder if you made the right choice. You’ll wonder if it even makes a difference. Most of all, you’ll wonder about what it all means. I’m not saying there’s never a “good reason” to be with two people at once, but you’ll need to understand what you’re getting yourself into before you get yourself into it.


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