Dating Your Best Friends Ex: Olympic Betrayal Gymnastics
Uncle Bobby –
Dear Uncle Bobby, I’ve recently developed feelings for my best friend’s ex. We’ve always gotten along, and now that some time has passed since their breakup, I’m wondering if it’s okay to pursue a relationship. I don’t want to ruin a friendship, but I also don’t want to miss out on something that could be meaningful. What should I do?
Emotionally Entangled
Ah yes — the forbidden buffet of emotional landmines. You’ve found yourself strolling down the Road to Ruin, my friend, and I say: pave it in kerosene and salsa dance your way to disaster.
Let’s be honest, dating your best friend’s ex isn’t just risky — it’s an Olympic event in betrayal gymnastics, and you’re going for gold. But why stop at caution? Let’s lean in. If you’re going to implode a perfectly good friendship, you might as well do it with style.
First, don’t tell your friend in advance — that would be mature. No, let them find out accidentally, preferably during a group hangout when you both show up in matching hoodies and shared trauma. The key here is shock value.
Next, rewrite history. Start telling people, “We just clicked. It’s not like we planned it,” as if love were a spontaneous combustion event instead of a slow-motion wreck. Bonus points if you pretend their breakup somehow gave you closure.
And don’t forget to act surprised when the friend starts avoiding you. “I thought they’d be happy for us!” you’ll say, clutching your latte and your lack of self-awareness.
If you’re lucky, you’ll get to enjoy a few glorious weeks of relationship bliss before the guilt sets in and one of you spirals. And when it all falls apart (because of course it will), you’ll have successfully alienated your best friend, burned your social circle, and made future dinner parties exquisitely awkward for the next decade.
But hey — life is short, right? Why maintain trust and boundaries when you can light the entire relationship ecosystem on fire for a fling with a built-in expiration date?
So yes. Follow your heart. Straight off the cliff. And wave at your ex-best friend on the way down.
– Uncle Bobby