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.

Kristy Swanson — 1996-1997

"8 Heads in a Duffel Bag" might not be an Oscar-worthy film, but we'd be willing to bet David Spade was glad he did the movie. It provided him the opportunity to not just work with Kristy Swanson but also to get close to the actor known for her role in "Buffy the Vampire Slayer." When the two began dating, who knew it would be the start of Spade's legacy with beautiful women ... even if the relationship was rumored to have lasted only nine months.

In 2002, Swanson spoke to Howard Stern, sharing a few intimate details about her past relationship with the comic. When Stern jokingly asked her if she was paid to date him, she replied, "David is awesome. We're still really good friends." When sidekick Robin Quivers asked why they weren't still together, Swanson shared, "I think we were better friends than we were dating."

She might have laughed when Stern asked if Spade was the best she'd ever had, but she did concede he was a "good lover." More importantly, Swanson seemed to agree with the sentiments of Heather Locklear, who recently credited Spade's generous manhood for why so many women end up on his arm.

Lara Flynn Boyle — 1998

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.

Krista Allen — 2001

Though it appears David Spade gravitates toward blondes, former "Baywatch" beauty and fellow stand-up comic Krista Allen definitely caught his eye. Not to mention the pair seemed to have a lot in common besides acting and making people laugh. In 2001, funnyman Spade showed up to the premiere of "Joe Dirt" alongside Allen, and sometime during their relationship, the lovebirds started talking business and brainstorming ideas for shows. 

According to TMZ, Allen claimed she came up with an idea for a reality show, which she pitched to David. Spade liked the idea, which involved celebrity judges holding fake auditions for a talent show, and agreed to go in on it with her, splitting the deal 50/50. When the relationship ended, and Spade later produced and hosted two seasons of a show called "Fameless," Allen took notice — and action. According to an article in Courthouse News, Allen was suing Spade for $1 million because he reneged on their deal to split the profits 50/50. The case was ultimately dismissed in 2017, and Spade had left yet another broken heart in his wake.

Julie Bowen — 2002-2003

"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."

Brittany Daniel — 2003-2004

Brittany Daniel's character, Brandy, in "Joe Dirt" might have a thing for mullets and swaying hips, but Daniel herself had a thing for David Spade. In fact, she still does if friendship and respect count. Daniel, probably best known for her role in the teen series "Sweet Valley High," appeared in both "Joe Dirt" films. And though the movies were about 14 years apart, she and Spade formed a strong friendship and were even rumored to be dating, according to E! News.

While promoting "Joe Dirt 2," the actor spoke to toofab and revealed her best on-screen kiss. Though it wasn't Spade — the highlight for the "White Girls" actor was Leonardo DiCaprio, of course — she had only sweet things to say about her former love interest. She told the magazine of Spade, "He's somebody that I've stayed really good friends with. He's one of my closest friends and I'll be friends with him forever. I care deeply for him."

Daniel said she and Spade remain close and she's ready for another "Joe Dirt" ... as long as she doesn't have to wait 14 more years.

Heather Locklear — 2006

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.

Pamela Anderson — 2007

Former Playboy Playmate Pamela Anderson might have a thing for bad boys and rockers, but there was something about David Spade that drew her in. The pair always seemed friendly, if not comfortable, when they appeared at events together. But when they were spotted together at Mirage's Jet nightclub in Las Vegas, paparazzi took notice, even capturing a picture of him adjusting her top and the "Baywatch" actor kissing the funnyman on the cheek — this even after he roasted her on Comedy Central, starting off his speech by turning the joke on himself and saying he was the only one who hadn't slept with her. 

Still, he ended by blowing her a kiss, which she returned on camera. Whether there was an actual relationship or not, it appears Anderson wanted to see what that kiss would be like in person. Years later, Spade had no problem including a jab at her in his Lights Out With David Spade monologue, mentioning her sex tape scandal with former husband, Tommy Lee.

Jillian Grace — 2007

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.

Nicollette Sheridan — 2008-2009

Obviously, actor Nicollette Sheridan doesn't kiss and tell, or maybe that's only when it comes to David Spade. According to People magazine, the pair was first spotted at Sheridan's 45th birthday party. Though they arrived separately, Spade was by her side when she blew out the candles, and he even winked at her. An onlooker told the magazine that it was the same restaurant the couple had been seen at weeks before during the grand opening, kissing at a table.

In early 2009, the British-born star of "Desperate Housewives" appeared on "The Ellen DeGeneres Show" and seemed to be playing it close to the vest. When DeGeneres asked her why Spade didn't mention to her that the two were a couple, Sheridan replied, "That's because we're friends. We're not dating." Of course, the talk show host couldn't miss an opportunity for a laugh, so she followed up with, "Friends with benefits?"

The blonde beauty didn't flat-out deny it, but when Spade then appeared on the show, and DeGeneres played the clip for him, looking for some answers, he replied, "I think it's less dating and more her killing time." The ever-casual Spade went on to say great things about Sheridan, dubbing her gorgeous and a sweetheart.

Charlotte McKinney — 2016

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 ..."

Naya Rivera — 2017

In 2017, David Spade, along with fellow comedian Fred Wolf, wrote the film "Mad Families." Further proof that Spade and Charlotte McKinney were "all good" was the fact that she, along with Spade's next love interest, the late Naya Rivera, both starred in the movie. According to People magazine, Spade and the "Glee" star were both in Hawaii at the same time, Spade on a comedy tour, Rivera with her friends. Coincidence? Maybe not since the two were spotted at the Halekulani Hotel pool. An onlooker reported that, though they were being discreet, the pair kissed and laughed together.

A source reported to E! News that Rivera and Spade had been dating for a few weeks but wanted to keep things private for the time being. Meanwhile, reports came out that they'd actually been spotted months before at a restaurant. Maybe this one was a slow-burn ...

E! News shared reactions from fans who were shocked at the odd pairing, as well as the age-gap of 22 years. When Rivera saw the headlines of her poolside PDA with funnyman Spade, she took to her Instagram stories (via Twitter), saying, "Holy s***, guys. The Easter bunny and the f***ing tooth fairy are for sure dating. I just saw them." Just a few short months later, US Weekly reported they were no longer seeing each other.