Crushing on my friend’s ex
When budding romance clashes with existing friendships
ok.. hear me out. i know this is going to sound bad, but i recently started talking to this guy over the summer. we really hit it off, and i think i'm starting to catch feelings. the problem is, my friend dated him last year and things didn't end well. he knows we are friends, but she doesn't know we've been talking. should i tell her? am i a bad friend?
Dear distressed-in-the-dms,
First, apologies for the delay. Even if this matter has been resolved, Auntie’s entire family wanted to pitch in to answer this for other readers. Our undergrad population isn’t that huge, so catching feelings for a friend’s ex is not an uncommon situation.
We must analyze why things didn’t end well between him and your friend. Perhaps he cheated, physically and/or emotionally? Or was it simply incompatibility? Or something else? I assume you know these details.
Our advice assumes your friend is able to look beyond her acrimonious breakup and be truly happy for you. If this isn’t the case, please think carefully about why this is so. What did he do? How did it affect her? If she ices you out over pursuing this relationship—either for reasons you agree with or reasons you don’t—would you understand why, or do you feel it would be unjustified? Would you feel betrayed in her shoes? Even though you seem pretty set on pursuing this crush, we encourage you to think through these important questions first.
One final note before you decide to move forward: we encourage you to reflect on whether your crush is likely to hurt you the same way he hurt your friend. Maybe this is not an issue, depending on their shared history, but it's worth thinking about beforehand.
Now we address the core of your question. First of all, you are not a “bad friend”—you caught feelings and are wondering how to act on them. The fact that you’re asking for advice suggests that you’re a conscious friend. To this end, we believe that you should tell your friend ASAP. It won’t be easy. To set the tone beforehand, consider texting them and saying that you want to talk about something important one-on-one. It’s best to keep it direct.
If you want to go forward with this, here’s how we suggest structuring the conversation:
The introduction: Keep it brief and say that you have to say something important first without interruption.
The body: Explain that you have romantic feelings for her ex, and that you recognize it can create an awkward dynamic if he’s around her.
The mitigation: Emphasize that while you’re in the talking stages, you won’t ever purposefully make her uncomfortable. This includes talking about him constantly or bringing around the guy without letting her know.
The conclusion: You highly value this friendship and you hope that if she ever feels uncomfortable, she’ll let you know. Also, you hope she can eventually be happy for you in the scenario this relationship works out, even though that’s a lot to ask from her.
The addendum: if the relationship ever starts to look more serious, you will restart dialogue with your friend, perhaps even at a predetermined time. As an example, maybe you promise to have another, more serious conversation about this situation in a few months, if applicable.
This outline might seem strange. We are not suggesting that you “hide” your crush from your friend. Rather, we suggest you compartmentalize your friendship and your romantic interests while you can. If your crush progresses into a full-blown relationship, maybe tensions will have cooled enough for your friend and then-boyfriend to have cordial interactions. Maybe not, though—the Matter family would need to write a whole other answer for that situation. That’s a very tough situation.
Honestly, there’s a pretty high chance that after this conversation your friend will be openly angry or surprised with you. If we were her, some of us might just walk out of the conversation. It will be scary, but having open communication like this will let her express her anger and confusion without it bubbling up. If your friendship is strong, we’re confident that you’ll find your way back. Also, don’t count your chickens before you hatch—you haven’t even gone on a date with the guy!
Bottom line: if you’re doing this, talk with your friend ASAP, and then see what transpires with your crush. Don’t do it the other way around.
Best of luck,
Auntie’s Family