Tori Spelling confesses that her only date with co-star Freddie Prinze Jr. during the filming of “The House of Yes” was derailed by her weed-smoking friends, killing a potential 90s Hollywood romance before it began.
Tori Spelling and Freddie Prinze Jr. were two of the most recognizable young stars of the late 1990s. Spelling was riding the waves of “Beverly Hills, 90210” fame, while Prinze Jr. had just become a heartthrob with “I Know What You Did Last Summer.” Their paths crossed in the 1997 independent film “The House of Yes,” a dark comedy where they portrayed siblings with unsettling dynamics. Off-screen, however, a different kind of chemistry sparked.
On a recent episode of her “misSPELLING” podcast, Spelling, now 52, delved into a nearly forgotten chapter from her youth: a brief, intense crush on Prinze Jr., then 22. “It was supposed to be this very innocent relationship on camera, and it kind of was off camera and he and I actually developed a thing for each other,” she admitted [Apple Podcasts]. The feeling was mutual, and they arranged their first—and only—official date.
But the evening never stood a chance. Spelling was living in an apartment shared with her best friend from college, who had a crowd of friends over that night. “They were all smoking weed,” Spelling recalled. As Prinze Jr. arrived to pick her up for a movie, she frantically warned her friends to behave, fearing the smell would cling to her and betray her. “I was like, ‘You guys, I have a date. Take this serious[ly]. He’s gonna smell this, he’s gonna think it’s me. It’s not me.'” Her pleas fell on deaf ears.
When Prinze Jr. entered, the group’s stoned antics began. “My friends were so weird, and they were so embarrassing,” Spelling said. The crowning moment? One friend slurred, “Freddie, is that Frederick?” and another asked Prinze Jr., “Do I call you Fred?” Spelling was mortified. “What is happening?” she remembered thinking. The date to see Jim Carrey’s “Cable Guy” felt like a lost cause from the start.
Despite the disaster, the two actors maintained a cordial relationship on set. “We stayed friends-ish,” Spelling noted, revealing that they shared a few “makeout” sessions in their trailer during lunch breaks. But the spark from that one ruined night never reignited into a full-blown romance.
Chronology of a Hollywood Near-Miss
- 1997: Spelling and Prinze Jr. co-star in “The House of Yes,” developing off-screen chemistry.
- Post-filming: They agree to a date, but Spelling’s apartment is full of smoking friends.
- The date night: Friends’ awkward questions and weed smell ruin the mood; they see “Cable Guy” but the connection fizzles.
- On-set aftermath: They share trailer kisses but nothing more, drifting to “friends-ish” status.
- 2002: Prinze Jr. marries Sarah Michelle Gellar after meeting on “I Know What You Did Last Summer” [Page Six].
- 2006: Spelling marries Dean McDermott, starting a family of five children.
- 2023-2025: Spelling’s marriage ends in divorce, finalized after two years [Page Six].
- 2026: Spelling reveals the ruined date story on her podcast, sparking nostalgia.
For Prinze Jr., the encounter was a minor footnote before a major life change. Just months after “The House of Yes” wrapped, he auditioned for “I Know What You Did Last Summer” on the set of Spelling’s “90210,” as she later learned. That role not only cemented his status as a leading man but also introduced him to Sarah Michelle Gellar. The two married in 2002 and have since built a family of four.
Spelling’s romantic journey took a different turn. She married Dean McDermott in 2006, and the couple welcomed five children over the years: Liam, 18; Stella, 17; Hattie, 14; Finn, 13; and Beau, 8. However, after 17 years, Spelling announced their separation in June 2023 [Page Six]. The divorce was finalized in November 2025, closing that chapter of her life.
This anecdote, while humorous in hindsight, taps into a universal fear: that our social circles can unintentionally sabotage our romantic prospects. For fans of 90s cinema, it fuels endless speculation about what might have been. Could Spelling and Prinze Jr. have been a power couple? Their brief connection remains a tantalizing “what if” from an era before social media exposed every dating misstep.
In today’s celebrity landscape, where PR teams meticulously craft narratives, Spelling’s raw podcast confession feels like a breath of fresh air. It reminds us that even Hollywood stars experience dating disasters far more relatable than red carpet perfection. The story also underscores how a single moment—a friend’s dumb question, a cloud of smoke—can pivot a life’s trajectory.
As Spelling reflects with a mix of amusement and regret, “He was very pure,” she said of Prinze Jr., highlighting the innocence that made the ruined date all the more poignant. Meanwhile, Prinze Jr. has navigated a steady family life, while Spelling continues to share her life’s chaos publicly.
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