EXCLUSIVE: A-List Age Gap Regrets — Why Showbiz's Most Glamorous Women are Looking Back in Anger at Dating Older Men
A-List women reveal age gap regrets as they reflect on relationships with older men in showbiz.
April 19 2026, Published 7:00 a.m. ET
RadarOnline.com reveals stars who raised eyebrows when they dated much older guys. Here's what they think about it now.
Hilary Duff
Thirty-eight-year-old Hilary Duff's new song Mature, about a younger version of herself dating an older man, has many fans believing Hilary is referring to ex Joel Madden, who she started dating when she was 16 and he was 25.
"I took a few artistic liberties just to make the song work structurally, but the gist is the gist," she admitted. "I was looking back on this relationship and thinking about whether this guy had a habit of dating younger women or whether I was 'special.'"
Hilary Duff said her song 'Mature' looks back on dating Joel Madden when she was 16.
Demi Lovato
While Demi Lovato has credited then boyfriend Wilmer Valderrama with helping her get sober, the 33-year-old, who dated him when she was 18 and he was 30, has changed her thinking on age-gap romances.
"For me, I was a teenager. And so to me, that's gross. If you are 50 and 60, you're fine," she said. "Even 30 and 40, that's not gross at all. But, I think when you're in those development years, you should absolutely not be with somebody that is older than you by that much. It's just unhealthy and toxic."
Demi Lovato said her relationship with Wilmer Valderrama felt 'unhealthy and toxic.'
Kylie Jenner
After meeting when Kylie Jenner was just 14, she and rapper Tyga, then 22, went public after her 17th birthday. They dated for a couple of years, then split amicably.
As Jenner, now 28, said on an episode of Life of Kylie: "I decided that I'm really young. I don't want to look back in five years from now and feel like he took something from me, when he's really not that type of person."
On 'Life of Kylie,' Kylie Jenner said she did not want to feel Tyga 'took something' from her.
Keke Palmer
"I was 15, he was 20," Keke Palmer, now 32, said of the older man she began dating while starring as a teen corporate exec on Nickelodeon's True Jackson, VP. It seemed fine at the time, she explains.
"In my mind, it was like: 'I got a full-time job ... Can't nobody understand me but a grown man.'" Only later did she realize the relationship was inappropriate, revealing, "The power dynamic put me in a place that harmed me in ways I couldn't have known."
Keke Palmer said starring on Nickelodeon's 'True Jackson, VP' coincided with a relationship she later called harmful.
Kaia Gerber
Kaia Gerber, 24, who has dated several older guys, including Austin Butler, 34, and Pete Davidson, 32, recently opened up about how being involved with men who were more established in their lives negatively affected her.
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Kaia Gerber said dating Austin Butler and Pete Davidson led her to change her 'personality and values.'
"I would completely just change my personality and values for someone," she said. "I always dated people older than me, so I was very willing to give up everything... which is actually not how you build respect and trust, and is not good in the long run."
