Inside David Spade's Dating History

David Spade is probably most known as a standup comedian and former cast member of "Saturday Night Live." Along with those impressive credentials, he's also been in dozens of movies and TV shows, including "The Wrong Missy" and "Grownups." He even starred in the popular television series "Just Shoot Me." But there's something else Spade has become famous for — some might even say legendary — and it appears to have nothing to do with his acting abilities. Or does it?

Spade might not look like leading man material, but there's something about the comedian and actor that draws in the most sought-after women in Hollywood. Could it be his witty charm or his approachable demeanor? Maybe it's as simple as his feathery mane of blond hair. Whatever it is, the funnyman has been spotted holding hands and getting cozy with dozens of gorgeous women, leaving many people shaking their heads in disbelief.

With a list this long, there's bound to be some conflicting accounts, but despite the fact that one of Spade's exes deemed him "undateable" and others have flat-out denied a relationship existed, there's plenty of photographic evidence to support the unions — not to mention, one of his "leading ladies" had Spade's love child. And still others look back on their time with the "Joe Dirt" star with fondness, including one starlet who credited Spade's, ahem, manhood for the reason he scores all the women. Here are the details on the past girlfriends of David Spade.

Though we don't see a lot of blockbuster hits these days with the name Lara Flynn Boyle attached to them, she was an "It" girl in the late '80s and '90s, with roles in hit shows like "The Practice" and movies including "Dead Poets Society" and the cult classic "Wayne's World."

David Spade didn't appear in that film, which stars several of his "SNL" buddies, but he still ended up crossing paths with Boyle and winning her heart. Per an interview in the now-defunct Details magazine (via GQ), he and Boyle were dating and went to a party, where Jack Nicholson proposed the three of them smoke. Given that no one in their right mind tells Nicholson "no," the three indulged. Spade later told James Corden, "Halfway through, uh, he goes, 'hey, Spade, I think I'm going to ask out your girlfriend.'"

Of course, the stand-up comic was caught off guard, but Boyle was somewhat affronted that her boyfriend didn't defend her honor. No one knows if that was the final nail in the coffin of their relationship. However, not long after, Spade discovered the two were seeing each other. The bad news was delivered by a phone call from The National Enquirer, alerting Spade his girlfriend was in a car crash with none other than Jack Nicholson.

"Modern Family" star Julie Bowen and David Spade only dated a year and still remain friends, but what does a guy gotta do to score points with Bowen? If you ask Spade, he probably couldn't tell you. He shared with Andy Cohen on Radio Andy just how far he went for Bowen, when according to him, he'd "messed it up." He shared that he convinced Stevie Nicks to call Bowen on her birthday when the two couldn't be together. Spade mused fondly, "She called and left her a message and then sang on it."

He'd hoped this would not only make up for his apparent flub but also help give his then-girlfriend a fab birthday. Unfortunately, the gesture wasn't grand enough, and Bowen ended up breaking up with the comic. For Bowen, who's starred in several television shows and movies like "Happy Gilmore" and "Conception," she saw the relationship a bit differently. When she spoke with Justin Long on his podcast, "Life Is Short," she said, "Sweet David, and I love him and I talk to him a lot and I will say this to his face, he's a lovely person and a good friend, not a great boyfriend."

David Spade might have started out in Heather Locklear's friendzone while she was getting a divorce from rocker Richie Sambora, but at some point their mutual admiration developed into a romantic relationship. Of course, Hollywood didn't believe in the union until a tattoo of a finch was spotted on the "Melrose Place" star's ankle. Finch was the name of the character Spade played on his series "Just Shoot Me." A source close to Locklear, however, told People that it was a symbol of her now being "free as a bird."

Yet, Spade and Locklear were spotted in public kissing and holding hands. Whatever really went on between the two, People reported in September of 2006 that they made a mutual decision that the timing just wasn't right. A source told the magazine that Spade was a comfort to Locklear and as of recently, that's still true.

In 2018, he spoke fondly of his former union with Locklear to Andy Cohen on Radio Andy. When asked if he was a good support for her, Spade replied, "I mean I love her. And she is, she was nice to go out with me and I will always be indebted to her because she was so nice, so fun, and no apologies, went out with me and didn't care, even though I'm sure she took some grief." He went on to tell Cohen that he checks in on Locklear, and she did the same when Spade's sister-in-law, Kate Spade, died.

It wouldn't be a huge leap to think David Spade met former Playboy Playmate Jillian Grace while dating another centerfold: Pamela Anderson. Apparently, whatever happened between Spade and Grace, who appeared (uncredited) in "House Bunny," was so brief, it scarcely could be labeled as dating. And yet, the two now share a child. According to HuffPost, however, the comic broke it off with Grace before he even knew she was pregnant. Initial reports painted the never-married Spade as apathetic, and one might wonder if he was waiting for confirmation he was, indeed, the father. Spade told TMZ, "I had a brief relationship with Jillian Grace. If it is true that I am the father of her child, then I will accept responsibility."

In August of '08, Harper Grace was born in Missouri, and as reported by People, Spade's rep confirmed he was the father. His rep said, "David and Jillian have been in close contact throughout her pregnancy and he plans to go see the baby during his first break from shooting 'Rules of Engagement.'"

And it appears the busy actor has made good on his promise and has been co-parenting Harper with Grace, appearing in public as a threesome and posting a rare photo of he and Harper with Spade's mother in front of a restaurant in Irvine.

Yes, Charlotte McKinney is yet another beautiful blonde on David Spade's arm. But, she's also funny! And she appeared alongside Spade in "Joe Dirt 2: Beautiful Loser." While neither the actor nor the model confirmed the dating rumors, TMZ snapped the couple coming out of West Hollywood hotspot Craig's, a place you don't go if you're trying to be discreet. Which means, Spade apparently wasn't holding a grudge against her for dishing to Page Six the previous year that Spade used cue cards and a teleprompter the entire time they were on the set of "Joe Dirt 2."

Spade did get his chance to retaliate, even if the digs were part of a skit, as they appeared together in a hilarious Coachella skit in Funny or Die, in which he questions McKinney and makes fun of her character.

The romance might have fizzled at some point, but the two seemed to remain friends when McKinney posted on Instagram about doing stand up at The Comedy Store. Tagging Spade and comedian Whitney Cummings, she wrote: "Got to do stand up with the help from these two ..."