When, in the hazy, beautiful summer of 2018, it was revealed that international pop star Ariana Grande was dating Saturday Night Live comedian Pete Davidson, the public response was one of giddy excitement. Here was this self-deprecating, goofy Staten Island native with one of the most beautiful and talented women in the entertainment industry—and they seemed to really be in love! Davidson, then 24, was not 100% new to the tabloids—he had previously made headlines for his relationship with Cazzie David, daughter of Larry—but his swift engagement to Grande catapulted him to cover-story status. He handled the new wave of obsessive attention on his personal life with an easy, unbothered confidence, inspiring Twitter users to give his whole vibe a very nice name. The Grande relationship was good for both his public perception and his career—it introduced him to a new audience and gave people a reason to tune in and watch him on SNL every week.
Unfortunately, Davidson’s tabloid journey did not end there. Grande and Davidson broke off their engagement last fall, and since then, Davidson has been photographed with a series of other high-profile brunettes ranging from Kate Beckinsale and Margaret Qualley. And with each new set of paparazzi photos—who could forget that meme-worthy Rangers-game makeout—the public’s estimation of Davidson has seemed to go down. Last week, when Page Six reported that Davidson was spotted exiting the apartment of 18-year-old model Kaia Gerber (daughter of Cindy Crawford and Casamigos co-founder Rande Gerber), Twitter commentators groaned. “Kaia ... noooooooooooo,” wrote New York contributor Chris Black, which nicely sums up the collective response.
If Page Six is correct in their implication, and Davidson is, in fact, dating Gerber, and the two are not "just friends," as a source stated, then this would be his fifth relationship with a beautiful celebrity woman in the span of two years. Is that bad? Well, everyone has their own opinions about what is good and bad, and we don’t need to get into those here. But I think we can all agree that with this potential new (very young) girlfriend, Davidson is quickly approaching what will henceforth be known as the Wilmer Valderrama Line.
It is rare for circumstances to converge in such a way that “dating a lot of beautiful and famous women” becomes a negative for a man. Before he married human-rights lawyer Amal Alamuddin, George Clooney had relationships with approximately nine million actresses and models and one former WWE Diva and people were like, “great.” Leonardo DiCaprio literally named his group of friends the “Pussy Posse” in the 90s and only recently have people even started to be like, “hmm.” In the history of Hollywood, being considered a playboy has almost always been a positive, or at least it hasn’t had a negative impact on the alleged playboy’s public image and career.
For a rare few, however, the dating stuff becomes the main story. This has been true of David Spade, who has the reputation of being a goofy comedian who somehow has a new famous girlfriend once a quarter. Since the late 90s, when he was starring on SNL, the 5’7” Joe Dirt star has dated Teri Hatcher, Pamela Anderson, Lara Flynn Boyle, Heather Locklear, Julie Bowen, Carmen Electra, Nicollette Sheridan … the list truly goes on. In 2017, he dated Glee star Naya Rivera! (Do you remember the pool photos?) His image as the regular boyfriend of unbelievably attractive women is so cemented in the public consciousness that even today, TMZ asks his ex-girlfriends what his secret is. (In 2017, Locklear provided the obvious answer: BDE.)
Then there’s John Mayer, whose fame quickly grew not just because of his music, which is fine, but because he spent most of the 2000s telling magazines all about his relationships with Jennifer Love Hewitt, Jennifer Aniston, and Jessica Simpson (never forget “sexual napalm”). Mayer has had more trouble with his reputation than Spade, thanks to those admissions and other inappropriate, racist statements he made during interviews with Playboy and Rolling Stone. He has recently acknowledged his perhaps permanently damaged public image on his friend Andy Cohen’s late night show, Watch What Happens Live!
“You’re friends with Jennifer Lawrence, who just doesn’t want anything to do with me,” he told Cohen on the show last summer. “Look, I don’t have the world’s greatest track record when it comes to celebrity relationships, so it’s amazing to watch your friends humor me on a friend level, but also keep a fair distance from me… if you are someone who cares about your image—and you take this job because it looks right, you don’t take that job—dating John Mayer at this point is conceptually just sort of a no-no.”
He was basically correct. When Katy Perry broke up with John Mayer in 2015 and moved on with Orlando Bloom, people seemed to think that was great, which is really saying something.
But few have struggled more to make the playboy image work for themselves than Wilmer Valderrama, who played the decidedly unsexy Fez on That 70s Show. As Valderrama was gaining recognition for his role on the show in the early 2000s, he started dating a string of famous actresses, and the tabloid drama quickly eclipsed his work. In the span of just a few years, Valderrama dated his co-star, Mila Kunis. He dated women who were friends with one another, like Mandy Moore and Minka Kelly. He dated Mischa Barton at the height of her O.C. fame, and a newly 18-year-old Lindsay Lohan. Then he dated Ashlee Simpson, who released the song “Boyfriend” after Lohan accused her of stealing Valderrama away. All of this ostensibly really happened! In 2009, tabloids even reported that Valderrama was “getting cozy” with Rihanna.
Valderrama, benefitting from an internet before social media was widespread, likely could have sailed through his dating choices relatively unscathed. But then he went on Howard Stern and talked about his ex-girlfriends in upsettingly vivid detail. He also seemed to be lying in several instances. Valderrama appeared on the show in 2007, and said he had taken Mandy Moore’s virginity when she was a teenager. “The sex with Mandy was good, but it wasn’t like warm apple pie,” he added, confusingly. (Moore quickly rejected Valderrama’s version of events.) He also claimed that Ashlee Simpson was a “screamer” and that Lindsay Lohan’s breasts were real. And he rated Jennifer Love Hewitt an 8 out of 10. (Hewitt denied ever dating him.)
Shortly after the appearance, E! News ranked Valderrama as one of the “Top 9 Worst Boyfriends in Hollywood,” alongside John Mayer, Anne Hathaway’s con-artist ex Raffaello Follieri, and uh, Mel Gibson. Hollywood careers fall apart for all sorts of reasons, and Valderrama came of age at a time when it was much easier for his white co-stars like Topher Grace or Ashton Kutcher to capitalize on the success of That 70s Show and land film roles. But his reputation for dating Lindsay Lohan and all of her contemporaries and loudly discussing it certainly couldn't have helped his career, and once the series went off the air in 2006, it was years before he showed up regularly in another hit show. He continued to work on TV in smaller roles, slowly escaping public consciousness, until he started dating the pop star Demi Lovato when she was, you guessed it, newly 18. In recent years, since their break-up in 2016, he's seen renewed career success, with recurring roles on NCIS and Grey's Anatomy, and has refrained from comparing women to desserts. But for many, his image remains stuck where it was in the early aughts.
Can Davidson avoid this fate?
In a few weeks, Davidson will turn 26. His rumored new girlfriend Kaia Gerber, meanwhile, turned 18 in September. This is certainly Valderrama territory. But we don’t yet know exactly what is going on. According to TMZ, Davidson and Gerber were spotted having brunch at Sadelle’s in New York last Tuesday. On Wednesday, Davidson was photographed leaving Gerber’s apartment in Soho. So maybe they’re "just friends." Maybe we’ll never know! Currently, Davidson is dropping in and out of SNL while filming movies, his career seemingly unhurt, if not bolstered by his high-profile dating life; for better or for worse, his personal drama has become a running bit on the show.
But public perception is a tenuous thing. Personally, I think it would be best for Davidson to avoid commenting and to one hundred percent never go on Howard Stern again. (The last time he appeared on the show, he was still with Grande, and he said nice things about her, and only commented on their sex life once, in the form of a self-deprecating joke. This performance leans more toward the much preferable David Spade end of the spectrum.)
He should also avoid tell-all interviews with Playboy and try not to rate women on a scale of 1-10. And I think it would be good for him not to be photographed with any more 18-year-olds after Gerber. A 24-year-old Wilmer Valderrama dating an 18-year-old Lindsay Lohan was one thing. A 30-year-old Wilmer Valderrama dating an 18-year-old Demi Lovato was another.
If Davidson can adhere to these guidelines and also refrain from commenting on the concept of virginity in his lifetime, he can safely avoid crossing the Wilmer Valderrama Line.
Got a tip about this or any other celebrity mysteries? Email Allie at email@example.com , or contact her on Twitter .
Sign up for our newsletter to get the best of VICE delivered to your inbox daily.