Woe Is Me! is a series in which The Swaddle team indulges your pity party with advice you’ll probably ignore.

Is it ever okay to date your ex’s best friend? We just broke up and I think her best friend is very similar to me, and quite the opposite of my ex. How do I not complicate this?

— Scoping Things Out

SM: I think it’s totally okay to date your ex’s best friend, but there’s a big BUT here. It’s a tricky situation with a lot of scope for jealousy, insecurity, and conflict — so all the three people involved need to be very sensitive and empathetic about the others’ feelings. Unfortunately, because you’re also in a way the third person in this equation, you need to make sure you’re extra sensitive towards both your ex and her best friend and don’t end up triggering a conflict in any way. That being said, you should also think about why you want to date your ex’s best friend. In my opinion, it’s something you should go ahead with only if you feel really attracted to and into this person. If the reasons are that she’s the opposite of your ex, or very similar to you, they might not be strong enough to actually pursue this, and make it through all the conflict that this kind of situation would inevitably entail.

KB: Thank you for the gift of the easiest task I’ve had to do all week: the answer is absolutely not, under any circumstances, should you pursue this. The only way this can possibly be uncomplicated is if you drop this idea right now and find another dating pool other than your ex’s friends. You asked if it’s “ever” alright to date an ex’s best friend, and the answer is that there is probably some tiny sliver of circumstances, where emotions are ever so perfectly aligned, where this would work for everyone and cause no emotional damage. But in the vast majority of cases, this would lead to a trail of broken hearts and friendships. Drop it and move on!

SK: I’m as conflicted as you: the practical part in me thinks it’s okay and the overlap shouldn’t complicate your desire for someone else, but the morality of this falls in a bit of a grey area. I think it totally depends on a) how you ended things with your ex partner and b) if your ex still has feelings for you. You mention your break-up was fairly recent — if it was on good terms, mutual, and there was no foul play from your side at least then I think you’re in the clear, at least morally. On the contrary, if it was quite mucky and you were crushing on your ex’s best friend even while you were in a relationship with her, then no! That’s just plain rude, insensitive, and super problematic. Plus, if your ex still has feelings for you, irrespective of whether the break up was good or bad, lay off for a bit before making a move on their best friend!

If you don’t want to complicate this, introspect all of the above, and if you still choose to go ahead because you’re madly attracted to this best friend, then have a conversation with your ex-partner. It should come from you, rather than them hearing it from someone else. Avoid resorting to explanations like “I have a right” or “I’m free to date whoever you want.” Long story short: just be a nice person!

RN: Categorically, this is a no. But in the interest of taking your feelings seriously, here are a few things to consider: Are you genuinely interested in the best friend, and do you have strong feelings for them? Or are you seeing them purely in terms of their compatibility with you and how different they are from your ex? If it’s the former, I understand that it’s complicated and can empathize with the fact that you can’t help how you feel, but I would still say that you can help what you do about it. If it’s the latter, this is not okay and is actually quite selfish. You could potentially jeopardize a close friendship by introducing yourself between them and pitting their personalities against one another, which is bound to create tension one way or another. It is also pretty inconsiderate of you to think about this immediately after your breakup.

If it’s just compatibility you’re looking for, cast your net wider than one of two types of people (ex’s best friend and best friend’s ex) who are out of bounds? Also ask yourself: did you break up with your ex because you wanted to be with her best friend? Does her best friend think the same of you? Is your ex aware of this being a possibility? Is everyone in on this and have you spoken about it with either or both of them? These are things which complicate things, whether you like it or not, because this is a situation which involves more people than just you and someone can end up getting very seriously hurt. You need to take responsibility for that possibility. By asking “how do I not complicate this,” it looks like you’ve already made up your mind and are seeking validation for your choice. But sorry, I’m voting no on this! But hey, there’s technically nothing stopping you, and I only hope that nobody gets hurt if you do go ahead with this.

DR: Hello! Breaking news: there are more than two kinds of people in the world. And also, someone being “similar” to you isn’t the default formula for a successful relationship. Sometimes, people happily spend their lives with someone that could be considered “opposite” to them, and sometimes, relationships based on the similarity between two partners don’t work out. So, rather than looking for “similar” or “opposite,” I think what you should look for is compatibility, perhaps? Also, what you like about this person other than your “similarities” might be an important thing to think about.

When relationships end, we’re often left with negative feelings towards our ex-partners, which can extend to their personalities too. The more time passes, the less intense these feelings get — and vice versa. Since you mentioned having just broken up, is it possible you are acting upon those negative feelings by wanting to date someone you’re describing as the “opposite” of your ex? And, maybe I’m overthinking here, but are you sure you don’t want to date your ex’s best friend out of spite towards your ex?

Look, social dynamics are complicated, in general — but we can’t avoid complications if we want to follow what we want. In this situation, as in any other, I’d say the complication would be worth it if you’re sure you really want to date this person — simply because you like them, and not because of any leftover feelings from your previous relationship. That would be unfair on this person you want to date. However, word of warning: these “social complications” can also make life difficult — so do weigh if it’s worth it for you before taking a step. Good luck!