Comedy Casanova: A Closer Look at David Spade’s Storied Dating History, From Lara Flynn Boyle and Heather Locklear to Naya Rivera

David Spade and Naya Rivera‘s pool PDA pics in Hawaii certainly made a splash with the millennial set last week, with some Glee fans seemingly coming of age in that exact moment as they saw a star of one of the seminal hits of their generation pair off with…

That guy from Saturday Night Live, like, 20 years ago. Chris Farley‘s BFF. The dude who isn’t Rob Schneider in Grown Ups.

In reality of course, Spade is incredibly successful, having starred in some of the most beloved and/or successful comedies of the ’90s and 2000s, as well as two sitcoms that made it into syndication, Just Shoot Me and Rules of Engagement. He’s also no has-been, churning out movies and TV cameos, talk show appearances and stand-up at a rapid clip, and he released his first memoir, Almost Interesting, in 2015.

But at 52, the perennial bachelor is also at a point when prancing around with 30-year-old Rivera, a star of the subsequent generation, is going to cause more conversation than his love life has in the past. And what a love life it’s been.

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