Sarah Michelle Gellar and Freddie Prinze Jr. have spent more than two decades as husband and wife, and the actress has chosen a nostalgic way to celebrate their latest marriage milestone. The 49-year-old star reached into the archives and shared several rarely seen images from the couple’s younger years.
The photographs capture a very different-looking Sarah and Freddie long before they became one of Hollywood’s most established couples. Now 50, Freddie appears alongside his future wife in snapshots taken during the earlier chapter of their relationship.

Rather than simply posting a traditional anniversary message, Sarah reflected on how surprising their journey would have seemed to their younger selves. Addressing her husband, she wondered whether the two people pictured could ever have imagined where life would take them more than two decades later. She also playfully pointed out that they have actually been together for 26 years, although they have been married for 24.
Freddie responded to his wife’s sentimental gesture by sharing her anniversary post through his own Instagram Story.
Their relationship traces back to the set of the 1997 horror movie I Know What You Did Last Summer, where the two actors worked together. Romance did not begin immediately, however. Their connection first developed as a friendship before eventually turning into something much more serious.

After their relationship blossomed, Sarah and Freddie eventually exchanged wedding vows at the El Careyes resort in Mexico. Twenty-four years later, they remain together and have built a family away from much of Hollywood’s constant attention.
The couple share two children, 16-year-old Charlotte and 13-year-old Rocky. Although both parents have spent much of their lives in the entertainment industry, they have deliberately protected their son and daughter from excessive publicity, allowing them to grow up largely outside the red-carpet spotlight.
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Even the beginning of Sarah and Freddie’s romance involved an unexpected twist. They had originally arranged to have dinner with a mutual friend who was supposed to arrive from another city.
When that friend missed her flight, the evening could easily have been abandoned. Instead, Sarah and Freddie went ahead with dinner on their own. The unplanned one-on-one meeting gave the longtime acquaintances an opportunity to connect on a different level and ultimately helped set their relationship in motion.
Years later, what started with a friendship and an unexpectedly changed dinner plan has become one of Hollywood’s longest-lasting marriages. Their newly shared photographs provide a rare look back at the young couple before marriage, parenthood and more than two decades of life together.