The former Cruel Intentions co-stars celebrated their decades-long friendship on Thursday with a visit to Disneyland, later taking to Instagram to share highlights from their fun-filled adventures.
For the outing, Gellar, 41, and Blair, 46, coordinated in olive green and beige ensembles, accessorizing with chic crossbody bags and a pair of Minnie Mouse ears, naturally.
"Is there a 21 year challenge?? On the left my 21 bday with @selmablair, on the right today (I know you all can do the math... I don't need to remind myself literally)," Gellar captioned side-by-side photos of the two at the theme park, taken 20 years apart. "Thank you @disneyland for a truly magical day!!"
Cruel Intentions, the 1999 drama which also starred Reese Witherspoon and Ryan Phillippe -- was re-released in theaters this past week in honor of the film's 20th anniversary. Gellar and Blair received the "Best Kiss" honor at the MTV Movie Awards that year for their steamy, onscreen smooch.
Reminiscing about the film and its cult-like following while chatting with ET last month, Gellar said that it was "sort of the first of its kind."
"Cruel was exciting because, for me, I look for things that'll make an impact and something that's different. And teen movies at that point were teen movies," she said. "It was daring and edgy, and some people were against the movie and didn't think it was a good idea. [But] I think we always knew that we were doing something really cool."
Gellar added that, two decades later, the cast is still close.
"We all see each other all the time. It's funny how your lives are intertwined," she shared. "Our kids are all around the same age, so we see each other. I doubt [we'll have] a televised reunion, but we have [personal reunions] all the time."