The Tao of David Spade: Hollywood’s Unlikeliest Pickup Artist

David Spade, 52, is rumored to be dating ‘Glee’ stunner Naya Rivera, 30, who is following in the footsteps of Pamela Anderson, Heather Locklear, and many more Hollywood beauties.


When you have to explain that your newly public relationship isn’t an April Fool’s joke, it might be time to re-evaluate your romantic life. Such is the sad tale of David Spade and Naya Rivera, a 52-year-old comic and 30-year-old former Glee star who I still only half-believe are actually doing it. On March 31, pictures leaked of the alleged couple cuddling in Hawaii. “The pair went for a short swim, hugged, and had lots of body contact in the pool,” a source dished to Entertainment Tonight. “They kept to one side of the pool where there was the most covering from prying eyes. Outside of the pool, they sat on lounge chairs and talked animatedly. They spent about an hour poolside together... They were very happy. They looked pretty comfortable together.”

Unfortunately for Rivera and Spade, the news of their possible coupling got way more press than Mad Families, the film they worked on together earlier this year. Written by Spade and starring Rivera, Charlie Sheen, and Leah Remini, Mad Families is exclusively available on Crackle, and has a 36 percent audience score on Rotten Tomatoes.

Spade and Rivera were presumably in town for “Here Comes the Funny,” a comedy tour featuring Spade, Rob Schneider, and Adam Sandler. Honestly, Naya Rivera and David Spade dating is the only possible explanation for the actress traveling to Maui to see a Rob Schneider show. That’s the kind of lineup you’d only endure for your 52-year-old boyfriend.

Rivera hasn’t exactly confirmed or denied her relationship with the former SNL cast member, addressing the rumors via Instagram story. “Holy shit, guys. The Easter bunny and the fucking tooth fairy are for sure dating. I just saw them,” she joked. If Rivera’s blasé attitude seems sort of dismissive toward her possible man-toy, just remember that there’s no way in hell David Spade knows what an Instagram story is.

While the veracity of this May-September romance is technically up for debate, I was ultimately convinced by an old Naya Rivera interview with Entertainment Tonight, in which the Glee alum confessed, “I like long hair on a white boy.”

Ladies, be careful what you wish for.

Explaining why the idea of Naya Rivera dating David Spade seems like a prank is sort of a cheap shot. Suffice to say, Rivera is a beautiful former Hooters waitress turned accomplished actress, mother, and memoir-writer. David Spade is 22 years older than her, and the kind of guy who stars in Grown Ups but still thinks that Grown Ups 2 is a good idea. Aside from playing Glee standout Santana Lopez, Rivera has made a name for herself as the rare celebrity who’s actually willing to spill the tea. Her 2016 book Sorry Not Sorry: Dreams, Mistakes, and Growing Up, joins the very short stack of celebrity memoirs that are actually worth reading (the only other book on this list is Bachelor villain Courtney Robertson’s I Didn’t Come Here to Make Friends). Rivera bravely wrote about her abortion, spoke candidly about her breast implants (“the best $8,000 I’ve ever spent”), and heavily implied that her ex-fiancé Big Sean cheated on her with a “little girl” whose name “rhymes with ‘Smariana Schmande.’” The next time you feel guilty gossiping about your ex to your friends or on social media, remember that Naya Rivera enshrined her Ariana Grande shit-talking in the Library of Congress.

But David Spade isn’t just an over-the-hill comedian who wears fedoras and does Capital One commercials—he’s an over-the-hill comedian who wears fedoras, does Capital One commercials, and has slept with some of the most beautiful women in Hollywood. Like Wilmer “Drakkar Noir” Valderrama and John “David Duke cock” Mayer, Spade is one of Hollywood’s hardest-working bachelors.

To be a celebrity lothario, you must either clear your schedule—dating is a big-time commitment!—or have a schedule that’s conveniently already clear. Just ask Valderrama, who took a seemingly involuntary hiatus from acting to focus on dating Demi Lovato. Spade, who would likely self-identify as a C-Lister, has taken full advantage of his decades spent adjacent to the spotlight. He’s dated models, Playboy playmates, and an entire ensemble cast of actresses: Tara Reid, Heather Locklear, Pamela Anderson and Teri Hatcher, to name just a few. While many of these rumored dalliances were just flings, Spade dated Modern Family actress Julie Bowen from 2002 to 2003—a whole year!

Of course, high-speed dating comes with its own specific obstacles, which, for David Spade, included the time that Jack Nicholson stole his girlfriend. “Nicholson asked Lara Flynn Boyle out in front of me, while we were all smoking a doob somewhere,” Spade recalled in a 2015 interview. “She got mad because I didn’t stick up for her,” he explained. “I said, ‘I’ve been in this town long enough to know when I’m outranked. You’re either gonna go out with him or you’re not.’ She goes, ‘No way. He’s worse than Trump!’” Apparently, Spade only learned that Boyle had taken Nicholson up on his offer—and that the two had gotten in a minor car crash together—via a phone call from The National Enquirer. “She and I didn’t talk too much after that.”

But don’t feel too bad for David Spade. After all, there’s an entire dark corner of the internet dedicated to praising his romantic prowess and analyzing his ability to score with leading ladies. As far back as 2008, Gawker wondered, “David Spade: World’s Greatest Ladies Man?” TMZ processed this interrogative through their horniest filter, asking, “How Does David Spade Get So Much Ass?”

How indeed? Apparently, David Spade was born this way.

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According to a 2008 Los Angeles Magazine story, a teenage David Spade was shocking classmates with his sex appeal long before Naya Rivera’s lifetime: “The entire student body at Saguaro High School knew he was the campus Casanova, a walking stick of catnip for every cheerleader and homecoming queen.” When pressed on his powers of seduction, Spade offered a bit of sage advice, “Be normal and kind of have your shit together. And be consistent and reliable. Just not a flake. Really, the thing is, not to be a superflake. Don’t be an asshole. Don’t be super cocky. Don’t be a show-off. Everyone for some reason feels the need to show off.” Dating in 2017: Have your shit together and don’t describe yourself as a Trump supporter on Tinder. Also, you probably shouldn’t refer to your dick as “a white supremacist.”

With the face of John Mayer, the inexplicable luck of Wilmer Valderrama, and the punctuality of David Spade, you could be canoodling with Naya Rivera or getting dumped by Katy Perry in no time.