Should You Ever Date Your Bestie's Ex?

Maybe or maybe not. Here's why it's complicated.

By
Published November 17, 2025
Kiersten Essenpreis

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Picture this: your close friends divorce after 40 years of marriage. “I’ve got maybe 30 years left,” he tells her after Christmas with their kids and grandkids. “I’m not happy, and I need more from my life.” You spend a year answering her sobbing 1 a.m. calls. She finally starts to laugh again. She goes out on three dates via the dating app OurTime. Then it hits you — after decades of shared dinners, pickleball games, holidays and weddings together, you miss him more than you could have imagined.

Or, what if your bestie doesn’t want him anymore? Or she’s come out as gay? Or she died last year from cancer? What if she’s sworn off sex and relationships for good? What if she declares, “You can have him”?

The questions now haunting you at 1 a.m.: Can you be friends with your bestie’s ex? Could you — gasp — date him?

Allison became one of my best friends back in ninth grade at our tiny Washington, DC, high school because we were simultaneously, and unknowingly, dating the same football player. For 45 years, my coda has been like an 11th commandment: THOU SHALT NOT DATE A BEST FRIEND’S EX. Because girlfriends are forever, and men come and go. Because loyalty matters. Because dating a bestie’s ex gets complicated.

But but but —

I adore Allison’s husband. He’s intelligent, funny, kind, handsome. I’ve watched him be a loving partner to her for three decades. I’d never try to break them up. But if the relationship died organically, I’d be tempted to pursue him, because he’s exactly the kind of partner I want.

As we get older (and older), there are fewer men to choose from. Especially men we’ve known inside out, and liked, for years. The should-you-date-your-bestie's-ex equation, like everything with aging, gets more complicated.

Suzanne Noble, 64, a sex and relationships expert and host of the wildly popular United Kingdom-based Sex Advice for Seniors podcast, actually introduced her ex-husband to a close friend after their divorce. The “new” couple has been happily together for well over a decade.

“Blessing your bestie and your ex — even playing matchmaker -— in the right circumstances makes sense,” Noble explains. “I’m happy my ex is with someone he loves and is a much better match for him than I ever was.”

Even so, there are five good reasons NOT to date your bestie’s ex. And ONE very good reason to do so.

First, the five cons.

1. Strain on your friendship. No matter what, this new romance will inject a weird vibe between you and Ms. Bestie. Is it worth it? Because besties ARE forever and men do still come and go, even Mr. Fabulous.

2. Tension between the two of you, your children, and his children. Justified or not, kids like their moms in neat little boxes. This pairing will explode their ideals of you, your bestie and him. Their kids may want to stick up for mom — or express their disgust with their dad and you. Your kids and theirs will become quasi-siblings. Be sure they can handle it.

3. Awkward family gatherings. Picture Thanksgiving with everyone around the table. Or … celebrating her birthday? Mother’s Day? My stomach clenches at the complexity of it all.

4. Self-conscious, comparative sex and relationship dynamics. Ugh! Does your self-esteem have the grit to know she had sex with him about 1,000 times more than you ever will? And maybe he liked sex with her better — they were younger, fitter, more energetic. You already know this couple very well. Can you take knowing their history even more intimately, and having it affect your daily thoughts and interactions?

5. Risk of an extremely messy breakup. Oy vey. Imagine the “I told you so” comments? But at least she’d know what you are going through.

“Love is complicated,” adds podcaster Suzanne Noble. “Good men are hard to find. Speaking personally, I’d probably avoid dating a bestie’s ex. But if he made the first move, if there had been a noticeable spark there, if it had been several months or years since they were together, if I had the blessing of my bestie … never say never.”

That’s a lot of ifs. But they’re all important to consider.

My old bestie, Allison, and I were not the only ones to date the same boy in our high school. Everyone invariably dated each other’s exes. You’d break up on Thursday, and by Friday night’s party, your lab partner would be smooching with your former boyfriend. It was brutal. It also built resilience.

Before we turned 20, we experienced the agony of being jealous, possessive and thin-skinned. Instead, we accepted that relationships end, and new ones start. We learned that demanding private grief and controlling who loves you and who they love next are understandable but self-destructive indulgences that fortify your heart in the long run.

Humiliating high school breakups coupled with torrid new romances taught me to let go of relationships when they’ve run their course. This lesson from youth has been far more valuable than ones in calculus or Spanish verb tenses.

Now, the long-awaited pro. You like your bestie’s ex. He’s a known quantity. So are you. The love feels genuine and grounded. You and your intended explain it all to your bestie, her children, your children, her mom. Everyone is okay with you trying to be a couple. Then — should you date your bestie’s ex? Not just yes, but hell yes. Life is too short not to.

What do YOU think? Should you date your bestie's ex? Let us know in the comments below.

Leslie Morgan Steiner is the author of four books, including The Naked Truth, which explores femininity, aging and sexuality after 50, and The New York Times best-selling memoir, Crazy Love. Visit her via her website, Facebook, Instagram and LinkedIn.