TBT: Sarah Michelle Gellar and Jerry O’Connell Dated After Going to the Same High School

Who: Emmy Award-winning actress Sarah Michelle Gellar, 45, and actor and television host Jerry O’Connell, 49. 

How They Met: Gellar and O’Connell go way back. The two met before they were both famous — in high school. The actors both attended the Professional Children's School in New York City, where Sarah was a freshman and Jerry was a senior in the early 1990s. 

And while there may have been an initial attraction, Jerry didn’t act on it until after graduation. “He never acknowledged me," Gellar recalled during an appearance on The Talk in 2021. She continued, directing her next statement to Jerry, who was previously a host on the talk show, "You never acknowledged me in school. It was only later that you would actually talk to me."

However, Jerry had his reasons for avoiding Sarah at the time. "Listen, I was a senior. I didn't want to come off as, like, too much of a predator,” he said. “I respected age differences and everything."

It’s not clear when Jerry eventually made his move, but in 1997, the pair were co-stars in Scream 2 and likely struck up a romance then. 

Why We Loved Them: They were living proof that dating your high school crush (or, at least someone you used to bump into in the hallways) years later isn't just a plot line from a rom-com, but can actually happen in real life. By the time Jerry and Sarah Michelle became a couple, she was approximately 20, while Jerry was 23. And despite it not working out in the end, they got to experience what some of us have only dreamed about.

When They Peaked: At the 1998 Emmy Awards — the only photographic evidence their relationship actually happened. Also, check the cute hand-hold.

The Breakup: The duration of Gellar and O'Connell's relationship remains unknown, but it could've only lasted a couple of years at most because, by 2000, Sarah Michelle was dating her now-husband Freddie Prinze Jr.

Where They Are Now:  As mentioned previously, Sarah Michelle's friendship with Freddie Prinze Jr. turned romantic after their first date in 2000. Two years later, they got married in Mexico, and in September 2009, the two welcomed their first child together, a daughter named Charlotte Grace, and three years after that, a son, Rocky James.

While dating Jerry, Sarah Michelle kickstarted her acting career as Buffy Summers on the teen TV series Buffy The Vampire Slayer. The show lasted for seven seasons, and during that time, she also starred in Cruel Intentions, Scooby-Doo, and I Know What You Did Last Summer. Most recently, she was cast as the headmaster in the Netflix movie Do Revenge, and just last month, her new TV show Wolf Pack debuted on Paramount+.

O'Connell went on to date many more famous women— Melissa Joan Hart, Giuliana Rancic, Geri Horner, aka Ginger Spice — following his split from Gellar. He eventually met his wife of 16 years, Rebecca Romijn. The two wed in 2007 and share 14-year-old twin daughters, Dolly and Charlie.

As for his career, Jerry continued to act, starring in Tomcats, Kangaroo Jack, and the Showtime series Billions, while expanding into television hosting in recent years — including gigs on The Talk, The Real Love Boat, and the game show Pictionary.