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Divorce Regrets: Celebs Who Wish They’d Stayed Married

Divorce Regrets: Celebs Who Wish They’d Stayed Married
  • PublishedMay 3, 2025

Oh, look at this—another batch of celebrities lamenting their divorce decisions like it’s some kind of surprise. You’d think a few million bucks and a hefty PR team would keep them out of these messy situations, but here we are. Bill Gates, Kris Jenner, and Will Smith lead the pack of stars who’ve openly shared their regrets about splitting from their partners. Yes, folks, even the elite aren’t immune to the pitfalls of love gone awry.

Let’s kick things off with Bill Gates, who, after parting ways with Melinda French Gates in 2021, admitted in a recent interview that he feels profound regret over the end of their 27-year marriage. The tech titan stated, “I wish I had done more to keep us together,” which is rich coming from the man who once had it all. Meanwhile, reality queen Kris Jenner opened up about her split from Caitlyn Jenner, saying she wishes she’d fought harder for their relationship. Can you believe it? The momager who orchestrates every detail of her children’s lives couldn’t orchestrate her own marriage? Shocking.

Then there’s Will Smith, who, in the wake of his tumultuous divorce from Sheree Zampino, expressed a deep sense of remorse, claiming, “I wish I would have worked harder to keep my family together.” It seems the Fresh Prince isn’t so fresh when it comes to relationships. And don’t even get me started on the likes of Jennifer Aniston, who has reflected on her past marriages, hinting that she might have chosen differently if she’d known how things would unfold.

These revelations raise an eyebrow, don’t they? Celebrities with access to the best therapists, life coaches, and relationship experts still manage to crash and burn spectacularly. It’s almost as if they think money can buy happiness—or at least a second chance. Spoiler alert: it can’t.

As we trudge through this celebrity regret parade, it’s clear that fame doesn’t shield anyone from the heartache of divorce. From the classic “what if” scenarios to the cringeworthy public apologies, these stars are serving up a hot mess of self-reflection. Who knew that even the elite feel the sting of lost love?

So, what’s the takeaway here? Maybe, just maybe, love is a battlefield—even for those perched on Hollywood’s highest pedestals. And that, dear reader, is why we can’t have nice things.

Sources: Celebrity Storm and People Magazine, E! News
Attribution: Creative Commons Licensed

Written By
Kai Montgomery

Kai Montgomery is a trailblazing journalist with a talent for breaking down the latest celebrity news with a sharp and unique perspective. Their work blends boldness with authenticity, capturing the essence of Hollywood's most talked-about moments while never shying away from the hard truths. Known for their fearless reporting and eye for detail, Kai brings a fresh voice to entertainment journalism. Outside of writing, they’re an avid traveler, lover of street art, and passionate about fostering inclusivity in all aspects of media.