Last month, Twitter had a field day when Dennis Quaid announced his engagement to a woman 39 years his junior. The 65-year-old actor proposed to 26-year-old Ph.D. candidate Laura Savoie after just five months of dating. He and the blonde beauty were vacationing in Hawaii when he popped the question. As if flexing his youthful hipness to his millennial fiancée, Quaid proposed via selfie, according to an interview with Extra. “She was actually taking a selfie of us,” he told Extra, “and I put the ring in front and said, ‘Will you marry me?’—and then she fell down.” He described the romantic moment as “kind of spontaneous” and “very much a surprise.”
However, fans and cynics alike were quick to point out that the couple’s love story sounded awfully familiar. In the 1998 hit movie The Parent Trap, Quaid plays dashing vineyard owner Nick, whose tween daughters (both played by Lindsay Lohan) are disturbed that his gold-digging fiancée (Elaine Hendrix) is, you guessed it, 26 years old. Even 20 years ago, the idea of Quaid marrying a stunning twentysomething was concerning enough to drive the entire plot of a feature-length film. Cheers abound when Nick gets back together with his age-appropriate ex-wife, played by Natasha Richardson (who, it should be noted, was still almost 10 years younger than Quaid).
Hendrix poked fun at her former costar on Twitter, retweeting the Page Six article about his engagement with the comment, “Watch out for those twins.” The meta tweet—made even more hilarious by the fact that Quaid himself has 12-year-old twins from his previous marriage—racked up over 500,000 likes.
Though Quaid’s relationship is packed with the kind of irony that guarantees online virality, he is far from the only leading man with a creepy penchant for dating much younger women. From the recurring joke about women aging out of Leo’s dating pool when they turn 25 to the decades of contention surrounding Woody and Soon-Yi, the May-December romance is an apparently timeless Hollywood fixture.
Here are others worth mentioning, in order from smallest age gap to largest.
Zach Braff, 44, and Florence Pugh, 23 — 21-year gap
Braff and Pugh were recently spotted getting cozy where else but a grocery store, canoodling in the same place that people buy their food. With critically acclaimed roles in Midsommar and Little Women, this is a big year for rising star Pugh.
Leonardo DiCaprio, 45, and Camila Morrone, 22 — 23-year gap
Ah, Leo—the poster child for exclusively dating twentysomething supermodels. He and Morrone, a model and actress, were first photographed together in December 2017 when she was 20. They’ve been going strong since.
Tommy Lee, 57, and Brittany Furlan, 33 — 24-year gap
It’s a tale as old as time. The Mötley Crüe drummer and the one-time Vine star struck up a romance after the rocker thirst-followed her on Instagram. They began dating in 2017 and walked down the aisle on Valentine’s Day of this year.
Michael Douglas, 75, and Catherine Zeta-Jones, 50 — 25-year gap
This A-list couple just celebrated their 19th anniversary yesterday. To celebrate the occasion, Zeta-Jones shared a letter on Instagram from Douglas’ famous father, Kirk Douglas. The elder Douglas advises, “To stay married, you must obey your wife! Keep practicing what I do with my wife.”
Dane Cook, 47, and Kelsi Taylor, 20 — 27-year gap
This eyebrow-raising couple celebrated their two-year anniversary of dating in May. Cook recently joked about his much-younger girlfriend on The Tonight Show Starring Jimmy Fallon, telling the talk show host, “Once in a while, I’ll say to myself, ‘You know what, where have you been my whole life?’ and then I realize she wasn’t alive for the first 28 years of it.” Yikes.
Sean Penn, 59, and Leila George, 27 — 32-year gap
The Academy Award-winning actor was first linked to George, an actress, in 2016 when she was 24 years old. Age-wise, the Australian-American beauty falls just between Penn’s two children with Robin Wright—Dylan, 28, and Hopper, 26. Her father is Law & Order actor Vincent D’Onofrio.
Richard Gere, 70, and Alejandra Silva, 36 — 34-year gap
Gere and Silva, together since 2014, are expecting their second child. The news broke earlier this month, only nine months after Silva gave birth to their first son in February.
Woody Allen, 83, and Soon-Yi Previn, 49 — 35-year gap
Allen was in a long-term relationship with Mia Farrow when news of his courtship with 21-year-old Previn became public in 1992. To make an unseemly relationship all the more disturbing, Previn was Farrow’s adopted daughter from a previous marriage, essentially making her Allen’s stepdaughter. The scandal was tabloid fodder during Allen and Farrow’s messy separation.
Mel Gibson, 63, and Rosalind Ross, 28 — 35-year gap
The volatile actor and his girlfriend have been dating since 2014. They share a two-year-old son, Lars—Gibson’s ninth child.
David Foster, 70, and Katharine McPhee, 35 — 35-year gap
At 70, Foster is twice the age of his new wife. The music mogul married American Idol alum McPhee in June after two years of dating. Foster was previously married to Yolanda Hadid, mother of Gigi and Bella Hadid.
Mick Jagger, 76, and Melanie Hamrick, 32 — 44-year gap
The legendary Rolling Stones front man (and notorious womanizer) has been in a relationship with American dancer Melanie Hamrick since 2014. They—somewhat amazingly—have a 3-year-old son together.
Don McLean, 73, and Paris Dylan, 25 — 48-year gap
This unlikely couple began dating in 2017, shortly after McLean divorced his wife of 29 years, Patrisha Shnier. Dylan’s résumé includes modeling for Playboy and Maxim and appearing on a 2017 episode of Catfish. In a gushing Instagram post, she calls the “American Pie” singer, “my baby, my beauty, love of my life, my everything.”