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Sarah Michelle Gellar Wants a Million Dollars From Howard Stern For Doubting 20-Year Freddie Prinze Jr. Marriage

Sarah Michelle Gellar and Freddie Prinze Jr. have a million-dollar bet to settle with Howard Stern. The couple is celebrating 20 years of marriage, and in honor of their relationship milestone, they’re calling out Stern for adamantly betting the couple would never make it at the beginning of their relationship.

On his radio show in 2001, Stern asks Prinze, “So, you will marry Sarah Michelle Gellar even though you know that it won’t last?” The Scooby Doo actor responded with “Oh, absolutely it will last,” and the two bickered back and forth about who would be right — to the point of making a million-dollar bet.

Stern belittles Prinze for nearly 15 minutes, telling him he’s going to cheat, “work with so many other hot chicks,” and that he “knows nothing” because he was 25 years old at the time of his and Gellar’s engagement. Prinze remains adamant that he doesn’t foresee any of this being a problem, and Stern doubles down, saying “I wanna make a written bet with you: In about 10 years, you’re gonna hunt me down and go, ‘Howard, I owe you money.'” Prinze responds with confidence, saying “We’ll do a written bet,” and adding, “We’ll write a contract right now.” Stern throws out a figure of a million dollars, and 20 years later, Gellar is coming to collect.

Sharing screenshots from the interview on her Instagram Story, Gellar tagged Stern and added, “What do you think?!?” She added another post to her story captioned “I think you owe us.” Prinze, a supportive partner as ever, reposted Gellar’s story to his own, adding “She will not forget” with two laughing emojis.

We hope Stern sticks to his guns about paying up just as much as he did when berating a steadfast 25-year-old Prinze — what an anniversary present that would be! — but we’ll settle for a good-natured apology as well.

Before you go, click here to see the longest celebrity marriages.
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