Some celebrity breakups don’t follow the standard route of a quiet period of self-reflection, sad playlists, and vague Instagram posts. There are plenty of celebrities who walk away from marriage and dive straight into romances that get everyone talking. Especially when their new man is quite a bit younger. It doesn’t really matter if these relationships were true love or chaotic rebounds. One thing is certain: these women did not care to move on in a subtle way, and why should they?
Madonna treated the rulebook like a rough suggestion
Madonna was married to Guy Ritchie for 8 years, but after they split up in 2008, she didn’t exactly pretend to be a demure divorced 50-year-old woman. In fact, for the next decade, she was linked to multiple younger men, including Jesus Luz and Brahim Zaibat, who were both almost 30 years younger than Madonna. That definitely made people uncomfortable, but Madonna isn’t exactly known for caring to make anyone comfortable. She has been publicly dating Akeem Morris since 2024, and they’ve been rumored to be engaged. Akeem is 38 years younger than Madonna, so even younger than her previous younger lovers. But hey, she’s Madonna, she does what she wants.
Kris Jenner went from a 20-plus-year marriage to Corey Gamble
Kris Jenner separated from Caitlyn Jenner in 2013, and they got officially divorced the following year. 2014 was also the year that Kris started dating Corey Gamble, who is 25 years younger than her. At first, people were saying that this is ridiculous and temporary, what could they possibly have in common? But they’ve been together this whole time and publicly profess their love for each other. That’s a relationship that’s been pretty strong for over a decade, so perhaps the public was too quick to judge them.
Robin Wright’s post-Sean Penn chapter looked very different
Robin Wright and Sean Penn had a long on-again, off-again relationship for years and finally got a divorce in 2010. After that, Robin started going out with Ben Foster, who is 14 years younger. They even got engaged at one point, but ultimately broke up in 2015. And while this relationship didn’t last, Robin talks about that period of her life very positively and with a lot of warmth. She says that she felt happier and more herself than before.
Jennifer Lopez got labeled fast, even though she said age was not the point
Jennifer Lopez was married to Marc Anthony for seven years before they divorced in 2011. She then went on to date Casper Smart (18 years younger than Jennifer) and briefly dated Drake (17 years younger). She then married her old flame Ben Affleck (3 years younger), but they got divorced in 2025. Tabloids were quick to notice that Jennifer seemed to be into younger men, but Jennifer pushed back, saying it’s about a person, not their age at all. As of 2026, Jennifer has been happily single and not really looking to date at the moment.
Sam Taylor-Johnson is the example people still discuss in all caps
This famous couple has a 23-year age gap, but that’s not even what shocks the public the most. It’s that Sam Taylor-Johnson left her marriage of 11 years in 2008 and met Aaron around the same time on the set of a film when he was only 18. They got engaged in 2009. Welcomed two daughters in 2010 and 2012, and got married later in 2012. The public and the tabloids often get into long passionate discourses over this relationship, and it’s not hard to guess why. But they’ve been happily together this whole time.
Julianne Moore quietly did this before it became tabloid bait
Julianne Moore isn’t often mentioned in the list of people who left their marriage for a younger lover, but that’s probably because there was no drama involved and her personal life seems to be very calm for Hollywood standards. She divorced John Gould Rubin in 1995 and later on married Bart Freundlich in 2003. Yes, Bart is 11 years younger than her, but they’ve been together for over two decades now and are still going strong.
Cher has made younger-men headlines so often it is basically a side career
Cher has been dating younger men for so long now that it doesn’t even feel scandalous anymore. After she divorced Sonny Bono, she dated many young men, including Gregg Allman (only 1.5 years younger), Val Kilmer (13 years younger), Tom Cruise (16 years younger), and Rob Camiletti (18 years younger). She’s been in a relationship with music executive Alexander Edwards since 2022. Edwards is 40 years younger than Cher. The media keeps a close eye on this relationship, and people keep commenting that that’s a very big age difference. Cher, however, says that age is simply not an issue for her. She’s Cher after all, she’s got her own opinions, and she doesn’t care what anyone else has to say on this matter.
Halle Berry’s dating history also shows the pattern, though with less of an age gulf now
Halle Berry and Eric Benét divorced in 2005. It was a very public and very painful breakup for Halle. She then moved on to date Gabriel Aubry, who is 10 years younger than her. She had other relationships after him and eventually found love with musician Van Hunt, who is only a few years younger than her. So it’s not quite a shocking age gap marriage, but Halle still fits the pattern of choosing to date younger after a divorce and not making age difference a huge deal in the relationship.
Susan Sarandon belongs here, with one important technicality
Susan Sarandon was never married to Tim Robbins, so he was never her husband. He was her partner for over 20 years. But when they broke up, she dated Jonathan Bricklin, who was 31 years younger than she was. They broke up after 5 years together, and Susan describes herself as single and unattached.
