Sarah Michelle Gellar recently celebrated the 20th anniversary of her marriage to actor Freddie Prinze, Jr. with a photo on Instagram—along with a since-expired Instagram Story “demanding” that radio personality Howard Stern pay she and her husband $1 million based on a bet he made with Prinze Jr. some two decades ago when they were engaged and planning their wedding!
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Interviewing Prinze on his show in August, 2001, Stern announced to the then-25-year-old actor that his marriage to Buffy the Vampire Slayer and Cruel Intentions star Gellar was doomed to fail after a few years. He even went so far as to talk about a making a hefty bet on it with Prinze.
Howard Stern Bet on Sarah and Freddie's Marriage
“I wanna make a written bet with you,” Stern said. “In about 10 years, you’re gonna hunt me down and go, ‘Howard, I owe you money.’”
“Put your money where your mouth is,” Stern insisted. “A million dollars, ten years!”
In his own inimitable and yes, brusquely humorous fashion, Stern was expressing his feelings that as Prinze Jr. and Gellar were both still young and up-and-coming stars, the relationship was doomed to fail.
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Two decades and two children later, Sarah and Freddie are apparently getting the last laugh—and they want what they’re owed!
“@SternShow, I think you owe us,” Sarah captioned on her Instagram post, which Freddie reposted with the comment, “She will not forget.”
The “bet” and “payoff” both seem to be good-spirited and in fun, of course, but it’s worth noting that Sarah Michelle Gellar and Freddie Prinze Jr. indeed enjoy one of Hollywood’s most successful and thriving marriages.
Sarah and Freddie Met While Making a Slasher Film
Gellar and Prinze Jr. met when they co-starred in 1997’s I Know What You Did Last Summer, the first entry in what was to become a popular slasher film franchise. Co-starring Jennifer Love Hewitt and Ryan Phillippe, the chiller was shot in the late spring of ’97, with Sarah and Freddie became fast friends over the course of the production’s 10 weeks of principal photography. (Seven of those weeks took place at night, which have proven to be fertile ground on a film set for planting the seeds of a future romance).
After the filming ended, Sarah and Freddie remained friendly and would often encounter each other at dinner parties, barbecues and other group gatherings with their wider circle of mutual friends and acquaintances.
The pair’s romance took hold later, three years after they first met, when they were scheduled to have dinner with a mutual friend from out of town.
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“That friend missed her flight, but we decided to still meet and catch up,” Sarah posted on Instagram back in 2020. “Now 20 years together, 17 plus married and two kids, we still go to that restaurant for dinner!
In her post, Sarah goes on to thank the mutual friend for not showing up that evening.
The two dove deep into their relationship quickly, with the romance playing out in front of the public’s eyes. Sarah and Freddie didn’t attempt to hide any of it from the world and they regularly began attending premieres, awards ceremonies and sporting events together. One particular evening in May 2000, during an NBA playoff game between the New York Knicks and the Miami Heat, found the two captured on the arena’s “kiss cam”—and the two didn’t hold back, much to the delight of the arena full of spectators.
Sarah Michelle Gellar and Freddie Prinze Jr. got engaged in 2001, a year or so after they first got together, and they were married in a low-key ceremony in Mexico less than a year later, in 2002.
Sarah and Freddie Starred in a Pair of Scooby-Doo Movies
That same year, the couple starred in the roles of Fred and Daphne in Scooby-Doo: The Movie, the live action/animated feature film adaptation of the long-running animated TV franchise. In a case of art imitating life, the film portrayed Fred and Daphne as a romantic couple, a step up from the animated series wherein their characters were simply goods friends who solved mysteries with their other pals and the show’s titular talking dog.
The movie did so well that it spawned a sequel, 2004’s Scooby Doo 2: Monsters Unleashed, in which the couple also starred, followed by a slew of live-action and animated spin-offs.
The couple have occasionally worked together since the Scooby-Doo films, but mostly as voiceover performers for animated projects, including the hit feature Happily N’Ever After and TV’s Robot Chicken and Star Wars Rebels.
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But clearly, it’s Sarah and Freddie’s life together that appears first on their mutual call sheets, especially after they welcomed their first child, daughter Charlotte Grace, in September 2009, and second, son Rocky James, in September 2012.
Meanwhile, it’s back to work for the pair, with Freddie having recently wrapping his co-starring role in Punky Brewster, the 2021 reboot of the popular 1980s of the same name, and Sarah co-starring in Do Revenge, the coming-of-age dark comedy that was just released on Netflix.
Coming up for Sarah is the upcoming Teen Wolf spin-off series Wolf Pack, for which she serves as both a star and executive producer.
Sarah considers this latest phase to be her “adult career,” which arrives following an extended hiatus from acting.
“I think I’ve earned it in a very honest way,” Gellar said in a recent interview with the New York Times. “I come with 40 years of experience. Some good, some bad, some in between.”
Sarah and Freddie's Marriage: 20 Years and Counting
It’s not surprising that Gellar looks at her lengthy career in much the same way she considers her happy and successful relationship with Prinze Jr.: as a fragile and vital organism that requires regular tending and care to ensure it will continually work and thrive.
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“I think we live in a very disposable world right now. When I was a kid, if your TV broke, you carried it to the repair shop and got your TV fixed. Now, if your TV breaks, you go get a new one,” says Gellar. “I think sometimes we look at relationships like that. You have to be willing to put in the work. That’s something we’ve always been willing to do. You have ups and downs, but you don’t walk away.”
Perhaps Howard Stern should check in on the Gellar-Prinze Jr. family again, and possibly lay down another bet on what the next decade will bring. This time, the wager could be for a new TV. We can’t know for sure, but the odds are that somewhere down the line, Howard might be spotted carrying over a new flatscreen to Sarah and Freddie’s house!
