Sarah Michelle Gellar and Freddie Prinze Jr.'s Relationship Timeline

If there's one celebrity love story that will make you believe in destiny, it's Sarah Michelle Gellar and Freddie Prinze Jr.'s. The pair first met on the set of I Know What You Did Last Summer in 1997, but it wasn't until three years later that they went on their first date. which happened to be a complete accident.

"We had made plans for dinner with a mutual friend and the person canceled. We decided to have dinner anyway and never looked back,” Gellar previously told People about how they first fell for each other after years of being friends. 

Since that fateful night back in January 2000, Gellar and Prinze Jr. got married and welcomed two children together, a daughter, Charlotte Grace, and a son, Rocky James. See how they got there with a complete look back at their relationship below.  

1997: Sarah Michelle Gellar and Freddie Prinze Jr. meet while filming I Know What You Did Last Summer.

Sarah and Freddie first met while filming the teen slasher flick I Know What You Did Last Summer in North Carolina in 1997, but they were strictly just friends. According to Freddie, Sarah didn't have her driver's license and he would drive her to the gym, which was over an hour away, allowing for plenty of time to get to know each other.

"I started driving her, and that’s when her and I became friends," Freddie told Us Weekly in 2020. "And we just would talk about life and stuff like that, and we had completely different philosophies on just about everything. ‘Cause she was a born and raised New Yorker and I was a born and raised L.A. kid, and we just looked at everything like night and day.”

Once filming wrapped, Prinze Jr. wasn't feeling a love connection, but still, the two kept in touch. "I just wanted to be friends with her because I thought she was too skinny and I wanted to cook for her. Because that’s what my family does,” he explained. “And so, we started this weekly barbecue thing at her house, and me and my cousins would come over and cook food for her and her friends. And then we’d make sure everybody ate, and that was kind of how our friendship began.”

January 2000: Sarah Michelle Gellar and Freddie Prinze Jr. go on their first date. 

Three years after they initially introduced, Gellar and Prinze Jr. planned to have dinner with a mutual friend, but as fate would have it, their pal couldn't make it and the two still decided to meet. "We were just two people at dinner catching up," Sarah told People of their accidental meet-cute. "We had a long car ride and a long dinner and things just happened."

In a 2016 Facebook Live interview, Prinze said Gellar won him over with her appetite. "A lot of girls back then in Hollywood—as far as the actresses—they didn't eat. They ate salad," he said. "I had gone on a date with a handful of them; they would never eat what I would eat." He continued, "Sarah came to dinner with me, and we sat down. She ate everything, including a crab that they let walk across the counter, then killed while it was alive in some oil and said, 'It's popcorn, try.'"

June 2000: Sarah Michelle Gellar and Freddie Prinze Jr. make their red carpet debut. 

Several months into their courtship, Gellar and Prinze Jr. made their relationship red carpet official at the 9th annual MTV Movie Awards. That night, Sarah won two awards—Best Female Performance and Best Kiss— both for her role as Kathryn Merteuil in Cruel Intentions.

April 2001: Sarah Michelle Gellar and Freddie Prinze Jr. become engaged.

After dating for over a year, Gellar and Prinze Jr. got engaged on April 13, 2001. A rep for the couple confirmed the news and revealed that they announced their engagement to their friends and family at Sarah's 24th birthday party the next day.

June 2002: Sarah Michelle Gellar and Freddie Prinze Jr. attend the Scooby-Doo premiere in coordinating outfits. 

Prinze Jr. and Gellar starred in their first movie together since their friendship turned romantic. In Scooby-Doo, Gellar played Daphne Blake, while Prinze Jr. took on the role of Fred Jones, and at the film's premiere, the couple adorably coordinated outfits on the red carpet.

September 2002: Sarah Michelle Gellar and Freddie Prinze Jr. get married.

On September 1, 2002, Gellar and Prinze Jr. got married at the El Careyes resort in Mexico. Gellar walked down the aisle with her mom, Rosellen, while wearing a strapless Vera Wang gown. Film director Adam Shankman, who worked with Sarah on Buffy the Vampire Slayer, officiated the ceremony. Other famous guests included Shannen Doherty, Wilmer Valderrama, and Dulé Hill.

March 2004: Sarah Michelle Gellar and Freddie Prinze Jr. attend the Scooby-Doo 2 premiere.

Prinze Jr. and Gellar reprised their roles as Fred and Daphne in the second installment of the live-action film Scooby-Doo and at the premiere, the two showed off their couple's style in coordinated casual outfits. Gellar wore white flare-leg jeans with a Y2K chiffon top with billowy sleeves and a bedazzled neckline, and Prinze Jr. paired a graphic T-shirt with jeans and a baseball cap.

September 2009: Sarah Michelle Gellar and Freddie Prinze Jr. welcome their first child. 

The couple welcomed their first child, a daughter, Charlotte Grace, on September 19, 2009. A rep for Gellar told People at the time that the pair were "over the moon" with their baby girl.

September 2012: Sarah Michelle Gellar and Freddie Prinze Jr. welcome baby no. 2.

Charlotte Grace became a big sister after her parents welcomed their second child, a son named Rocky James, on her third birthday (September 19, 2012). “They are thrilled that Charlotte [has] a little brother,” a source close to the couple told People. “They love their little girl more than anything in the world and know that love will only multiply.”

January 2020: Sarah Michelle Gellar celebrates the 20th anniversary of her and Freddie Prinze Jr.'s first date. 

Gellar recalled the details of her and Prinze's accidental first date, 20 years later.

"20 years ago this week, my friend @realfreddieprinze and I were supposed to have dinner with a mutual friend from out of town. That friend missed her flight, but we decided to still meet and catch up. Now 20 years together, 17 plus married and two kids, we still go to that restaurant for dinner," Gellar wrote on Instagram alongside side-by-side photos of her and Prinze Jr. then and now. She added, "So thank you @sloaney77 for not showing up for dinner."

January 2023: Sarah Michelle Gellar and Freddie Prinze Jr. make a rare joint red carpet appearance. 

Gellar and Prinze Jr. attended their first red carpet event together in more than 10 years at the premiere of the actress's new Paramount+ series Wolf Pack.

July 2023: Sarah Michelle Gellar shares photos from her family vacation with Freddie Prinze Jr. and their two kids. 

Gellar and Prinze Jr. took a family vacation with their two children, Charlotte and Rocky, to Florence, Italy in July 2023, and to commemorate the trip, the actress pulled a rare move and shared a handful of sweet family snaps on Instagram.

“siamo arrivati (let the Prinze family Italian adventure begin) #florence," she wrote in the caption of her post.

October 2023: Sarah Michelle Gellar and Freddie Prinze Jr. ushered in spooky season with coordinating fall outfits.

Gellar and Prinze Jr. kicked off the start of spooky season with a rare public date night at a Halloween theme park. They both dressed casually for the occasion, with Gellar wearing jeans, a leather bomber jacket, and sneakers, while Prinze Jr. opted for chinos and a zip-up hoodie.