Love in the Age of Legal Contracts: What Celebrity Prenups Really Mean

It’s the question that follows every celebrity proposal: Do you really love each other if you’re signing paperwork first?

Baylen Dupree, star of“Baylen Out Loud,”just joined the growing roster of famous faces willing to answer that question with a resounding yes. After marrying Colin Dooley in May 2026, Dupree confirmed she’d signed a prenup—and her perspective on it is refreshingly candid.“I’m just excited to make everything joint,”she said on the May 26, 2026 episode of the“Howie Mandel Does Stuff”podcast.“I don’t care about the money. I just care that we’re united.”It’s a sentiment that flips the script on how prenups have traditionally been framed: not as a hedge against disaster, but as a practical conversation between partners who are serious about building something together.

The celebrity prenup landscape is surprisingly fractured. While Khlóe Kardashian has spent years evangelizing prenups as essential financial armor—”Everybody needs a prenup!”she told E! News back in June 2011—plenty of A-listers have opted out. Justin Bieber and Hailey Bieber married with no legal agreement in place. Jessica Simpson, who married Nick Lachey in October 2002 without one, later told Dr. Oz that she regretted that decision. On the flip side, Gabrielle Union made a prenup a dealbreaker when she married Dwyane Wade, learning from her 2001 marriage to Chris Howard that protecting your own assets matters.“When you have your own stuff, you don’t need to worry about anyone else’s stuff,”she explained in February 2014.

The real story here isn’t whether you sign or don’t sign—it’s what your choice says about how you’re approaching partnership. Some couples, like Christina Hall and Josh Hall, skipped the prenup entirely in 2022, only to face a contentious split in July 2024 where asset division became a public battlefield. Others, like Gwen Stefani, learned the hard way: no prenup with first husband Gavin Rossdale meant she and he were entitled to equal halves of everything earned during their 13-year marriage. When they split in August 2015, sources said Rossdale agreed to an“unequal split”favoring Stefani—but she didn’t take chances the second time around. Before marrying Blake Shelton in July 2021, she had a prenup locked in.

What Dupree’s openness about her prenup hints at is a cultural shift: the death of shame around having these conversations. Stassi Schroeder, the Vanderpump Rules alum, put it beautifully in February 2020:“I feel like people look at prenups as like a dirty thing that we shouldn’t talk about, but honestly, I feel like there is some romanticism to it. Being able to be so close to someone that you’re willing to have those uncomfortable conversations…it’s brought me closer to Beau the more that we talk about it.”

That’s the real takeaway. Whether celebrities are signing prenups or betting everything on love, the ones who seem to thrive are those who’ve actually talked about it—who’ve treated the question as what it really is: a conversation about values, not a vote of no confidence. Dupree gets it. And maybe, just maybe, the rest of us should too.