Tori Spelling Reveals Why Her Date with Freddie Prinze Jr. Failed

Tori Spelling recently opened up about her short-lived romantic involvement with actor Freddie Prinze Jr., revealing details about their one date and why it ultimately did not work out. The discussion surfaced on the March 5 episode of Spelling’s misSPELLING podcast, where she described the early stages of their relationship marked by both on-camera innocence and off-camera connection.

Spelling, 52, explained that although their romance was brief, she and Prinze Jr., 49, actually developed feelings for each other. However, despite their attraction, Spelling confessed the date was sabotaged by her close friends, contributing to the relationship’s downfall.

How Friends Interfered with Their Date

At the time, Spelling was living with her best friend in an apartment in Universal City. She recounted how she had invited several friends over, many of whom were home from college and smoking marijuana. Worried about the impression her friends might make, Spelling urged them to behave since Freddie would be visiting.

Nonetheless, the situation quickly became uncomfortable when Prinze Jr. arrived. According to her, her friends acted awkwardly and embarrassing themselves in front of him. One friend mistakenly addressed Freddie Prinze Jr. as “Frederick,” which drew a confused reaction from both Spelling and Prinze Jr. The actors still went ahead with their date despite the rocky start.

Freddie Prinze Jr.
Image of: Freddie Prinze Jr.

The Date and Their Shared Interests

Spelling described Freddie Prinze Jr. as quite shy but genuine, and the pair made an effort to spend time together. They shared multiple kisses during lunch breaks on set, displaying their mutual interest. Following that, Prinze Jr. took Spelling on a proper date to see the movie Cable Guy.

Though their personal interests diverged, with Prinze Jr. being passionate about comic books and Spelling more into DIY crafts like decoupage, the two connected enough for Spelling to gift him a wooden box decorated with comic book imagery. However, despite these moments of chemistry, the relationship did not progress further.

Maintaining a Friendly Connection Afterward

Though their romantic involvement ended quickly, Spelling shared that they remained on friendly terms. She recalled an occasion when Freddie visited the set of her show 90210 unexpectedly while auditioning for a movie role.

“So that was it, but we stayed friends-ish,”

Spelling said.

“I still remember Freddie coming to set 90210 and I didn’t know and it was after and I was like, ‘Oh, hi hi,’ and he’s like ‘Oh hi.’ And he’s like, ‘Oh, [the makeup artist] knew I was coming. I have an audition for this movie.’”

Tori Spelling, Actress

Freddie Prinze Jr. was auditioning for I Know What You Did Last Summer, a film that eventually launched his career and where he met his future wife, Sarah Michelle Gellar. The couple wed in 2002 and have two children: daughter Charlotte and son Rocky. Spelling’s brief romance with Prinze Jr. thus predated his lasting relationship with Gellar.

Tori Spelling’s Later Life and Relationships

Following her short romance with Freddie Prinze Jr., Tori Spelling married Dean McDermott in 2006. The couple shared five children: son Liam, daughter Stella, daughter Hattie, son Finn, and son Beau. McDermott also has a son named Jack from a previous marriage to Mary Jo Eustace. Spelling and McDermott separated in 2024, with their divorce finalized the next year.

Though she did not find lasting love with Prinze Jr., Spelling’s reflections on the brief romance illustrate how quickly relationships can be shaped and shifted by surrounding circumstances and social dynamics.

The Lasting Impact of a Fleeting Connection

Tori Spelling’s candid recount of her fleeting romance with Freddie Prinze Jr. sheds light on the unpredictability of early relationships, particularly under public scrutiny. The influence of friends, nerves, and timing all played a role in why the relationship did not deepen.

While Prinze Jr. went on to build a long-term family life with Gellar, Spelling’s experience reveals the challenges actors face trying to maintain personal connections amid busy careers and social interference. Their story serves as a poignant reminder of how even promising encounters sometimes falter before they can flourish.