Tessa ReneeCrisis:
Dear Tessa, I was swiping on a dating app and ended up matching with my ex’s best friend. He’s cute, funny, and actually seems interested. But is this too messy, or should I go for it?
— Torn Between Cute and Chaos
Congratulations, babe, you just unlocked the toxic level of the dating game. Matching with your ex’s best friend is like playing with fire while holding gasoline: thrilling, dangerous, and guaranteed to make someone’s group chat explode.
Let’s get real: is it messy? Absolutely. But sometimes messy is the point. If you’re still hung up on your ex, then swiping right on his bestie is just a petty rebound in cute packaging. That road leads straight to drama-ville, population: you. But if you’re genuinely feeling the connection and not just trying to send a smoke signal to your ex, then maybe, just maybe, it’s worth exploring.
Here’s the line: don’t do it to get even. Do it because you actually like the guy. Otherwise you’re just the villain in someone else’s story — and spoiler, they’ll all paint you that way anyway. If you can handle the whispers, the side-eyes, and possibly being the topic of his next boys’ night roast, then own it.
Final Thought: Dating your ex’s best friend isn’t wrong if it’s real. But if it’s just revenge in disguise, you’re not building love — you’re building drama.
Disclaimer: Menace Mail is written with equal parts sarcasm, savage honesty, and a little too much iced coffee. These answers are not licensed therapy (shocking, I know), just unfiltered perspective. If it stings, maybe that’s the point. It is pure satire and for entertainment purposes only. The scenarios, “advice,” and commentary are exaggerated, over-the-top, and not meant to be taken literally. If you’re here for actual relationship guidance, you’re in the wrong inbox and on the wrong blog.
Tessa Renee
