Shawn Southwick, Larry King

Age is just a number for celebs (unless it comes to landing jobs when you’re a woman creeping into the latter half of her 30s). The red carpet doesn’t discriminate in the romance department, and young stars have notoriously shacked up with men old enough to be their fathers. The age-old trope of a middle-aged movie star dating a young, pretty blonde is older than the aging celebrities who make it a cliché, but are these relationships actually meant to last?

For many, ultra-young wives are a second, third, fourth, or eighth try at love (sorry, Larry King!). Celebs such as Steve Martin and Michael Douglas have formed tight-knit relationships with their younger spouses, while other young stars, such as Amber Heard, have struggled to deal with the dynamics of a partner in another peer group. There’s only one thing the relationships in this story all have in common: all these men married women young enough to be their daughters.

Clint Eastwood and Dina Ruiz

Dina Ruiz, Clint Eastwood

Clint and Dina Eastwood (formerly Ruiz) had a really long run — 17 years to be exact. The couple wed in 1996 and hid from the Hollywood spotlight in the seaside town of Carmel, Calif. Somewhere along the line, their 35-year age difference may have gotten the best of them, because according to People, a fundamental difference in values prompted the couple to call it quits.

Eastwood, who was 65 at the time of his second wedding in 1996, is notoriously private. This was reportedly at odds with Dina’s reality show, Mrs. Eastwood and Company, which raked in an average of 1 million viewers per episode. Eastwood occasionally appeared on the show, which also featured his daughters, Morgan and Francesca Eastwood, but he was reportedly furious that Dina put the kids on TV. Halfway through the first season, Clint reportedly stopped wearing his wedding ring, and the couple allegedly moved into separate rooms in their home.

During this rough patch, Dina reportedly turned to high school friend Scott Fisher for emotional support. Fearing their relationship wasn’t platonic, Erica Fisher (Scott’s wife) reached out to Clint. Erica and Clint sparked a romance, and Dina went to rehab for a broken heart — or so say some sources. In the following months, Dina hooked up with Scott and eventually married him in 2016. Basically, the Eastwoods and Fishers played out a really dramatic episode of Wife Swap.

Doug Hutchison and Courtney Stodden

Courtney Stodden is one of those celebs whose career is perplexing. The former beauty pageant queen is seemingly famous for being famous — or maybe she’s famous because she married middle-aged Lost actor Doug Hutchison when she was just 16 years old and he was 51. They share a whopping 35-year age gap. Stodden’s unconventional marriage led her to reality fame on shows including Couples Therapy and Celebrity Big Brother. Her relationship has also been tabloid fodder, especially when you consider the fact that her parents had to cosign on her nuptials since she was legally too young to consent.

Stodden proceeded to give the nation heebie jeebies by regularly sharing uncomfortable tidbits about their controversial union, including calling the then-51-year-old a "tiger" in bed. Following their disastrous split in 2017, Stodden momentarily issued a public Instagram plea begging Hutchison to take her back, but then allegedly changed her mind again. They were married for a short six years, but to be totally fair, that was a huge chunk of Stodden’s young life.

In 2017, her mother allegedly admitted the union was a total mistake. It was a few years too late, but what do you expect from the woman who allegedly had an emotional affair with her daughter’s husband.