Jerry O’Connell has never been shy about poking fun at himself, and his latest confession is no exception. This time, it involves a very brief romance with none other than Sarah Michelle Gellar.
O’Connell recently appeared on Kelly Ripa’s “Let’s Talk Off Camera” podcast where he revealed his history with the “Buffy The Vampire Slayer” alum. Ripa, a fellow ’90s star, hosts the podcast to talk about insider Hollywood drama, secrets and personal, off-limits topics.
‘One and Done’
When they were both young stars navigating Hollywood together, O’Connell and Gellar went out on one date; exactly one.
“We were very young, we were kids,” O’Connell began. “Sarah Michelle took one look at me and was like, ‘I got to get away from this drunk.'” O’Connell has been open about his struggle with alcoholism and has been sober for 13 years.
According to O’Connell, Gellar “needed a date to the Emmys” in 1998. The “Scream 2” co-stars were both rising to fame at the time, but they weren’t a match. They were “one and done.” Their date to the Emmys was the first and last outing together. He recalled Gellar’s reaction as polite but final, essentially wrapping up the evening after one memorable night out and not looking back.
No Hard Feelings, Though!
The two stars still see each other “around the neighborhood,” too. “I see her and her husband, and her husband is like a black belt in jiu jitsu–so please, I don’t want any beef with these people,” O’Connell joked about the couple. On a more serious note, he called them a “beautiful family.” He clearly finds that detail more intimidating than a decades-old rejection.
Gellar, 49, and O’Connell, 52, found their spouses just a couple of years removed from each other. Gellar married Freddie Prinze Jr. in 2002 after they met on the set of “I Know What You Did Last Summer” (1997). The couple has two children together, daughter Charlotte, 16, and son Rocky, 13. They will celebrate their 24th wedding anniversary in September.
O’Connell tied the knot with actress Rebecca Romijn in 2007, who convinced the “Stand By Me” alum to settle down, calling her the biggest turning point in his life. Their nearly two-decade marriage has become one of Hollywood’s most enduring pairings, and O’Connell has spoken affectionately about their life together in interviews since.
“I was very immature,” he said in an interview while promoting “Summer’s Last Resort” on FOX. He said he knew that “life wasn’t gonna get better than this” for him when Romijn made her intentions of starting a family clear, and he remains “so glad” that he settled down. The couple have twin daughters, Dolly and Charlie, who are both now 17 years old.
It’s a fun little piece of ’90s trivia: two beloved stars who briefly crossed paths on the red carpet before finding their happily-ever-afters elsewhere. Leave it to Jerry O’Connell to be the punchline in his own stories and to bring it back up decades later with a laugh.



