Entertainment Movies Sarah Michelle Gellar and Selma Blair's Friendship Photos Through the Years The Cruel Intentions actresses have been friends for almost 25 years By Andrea Wurzburger Andrea Wurzburger Andrea Wurzburger is a former features writer at PEOPLE. She left PEOPLE in 2022. People Editorial Guidelines Published on July 1, 2022 12:09PM EDT Close 01 of 16 '90s Babies Selma Blair and Sarah Michelle Gellar. Sarah Michelle Gellar/Instagram Sarah Michelle Gellar shared a sweet throwback, taken in 1998 on her birthday, in honor of her pal Selma Blair's 50th. "If I told that little girl on the right, that the girl to her left was going to be her lifelong friend … she would say 'I know,' " Gellar said in the caption. 02 of 16 Cruel Intentions Everett Collection The pair met while filming 1999's teen film, Cruel Intentions, in which their characters shared a now-iconic, oft-recreated, kiss. "I mean, why wait? We do it all the time. I love that girl," Gellar told PEOPLE about kissing her former costar and dear friend. "She has a very smooth, very easy face to kiss." 03 of 16 Sealed with a Kiss Frank Micelotta/Getty The pair's onscreen smooch earned them a MTV Movie & TV Award for best kiss in 2000. 04 of 16 Greatest of All Time selmablair/Instagram The pair celebrated their win once again, 20 years later at the MTV Greatest Of All Time Awards, with Blair captioning a series of photos with Gellar, "Looking back 20 years ago... A kiss. Between two young actresses. On screen. In a mainstream teen movie. In 2000. It was a sweet and delicious kiss for my character, Cecile. And she wanted more. And I must say it was a really good kiss. What feels so delicious to me now is how it isn't shocking in 2020. It stands for a shift in thinking. I am honored to be the GOAT kiss with my dear friend @sarahmgellar... who has been by my side through the excitement, the slow times, the changes, the kids, in sickness and in health." 05 of 16 Red Carpet Pals Kevin Winter/Getty Gala gals! The dynamic duo both wore black dresses to the Divine Design 2003 Gala in December 2003. 06 of 16 Selfie Time sarahmgellar/Instagram Gellar gushed that Blair was the "best date ever" to see Pink in concert in June 2018. 07 of 16 Girls' Night Out Sarah Michelle Gellar/Instagram In October 2017, the duo had another magical girls' night out! Gellar captioned a selfie of the pair, "Sometimes you make a decision to go out, even though you are tired, and magic happens. @therealselmablair my girl crush, now and forever." 08 of 16 Supportive Pal Michael Kovac/Getty Blair was on hand to support Gellar, who is the co-founder of Foodstirs, at the Gilt & Foodstirs exclusive cupcake kit celebration in October 2016. 09 of 16 Reuniting with Reese sarahmgellar/Instagram In March 2021, Gellar reminisced about attending the opening night of Cruel Intentions: The '90s Musical Experience with Blair and their costar Reese Witherspoon in 2017. 10 of 16 Head to Head Selma Blair and Sarah Michelle Gellar. Alberto E. Rodriguez/WireImage Blair, who has been very open about her experience with M.S., got some support from her close friend at the 26th Annual Race to Erase MS Gala in May 2019. 11 of 16 Grateful for Each Other Sarah Michelle Gellar/Instagram When Gellar and Blair were evacuated from their homes due to wildfires in October 2019, they managed to find some comfort in each other. Gellar wrote on Instagram, "I left my house on Monday am at 3am when we were evacuated, with the clothes on my back (since been washed don't worry) and my family. I'm definitely scared and emotional, but then I get a surprise of @selmablair and now I can't stop smiling. These moments remind me to be grateful for all the blessings I have, and Selma you are certainly one of them." 12 of 16 Reunion Ready Selma Blair/Instagram It's another Cruel Intentions reunion! Gellar and the film's director, Roger Kumble, visited Blair in February 2020. Blair wrote of their time together, "I can't show how good it feels to have my friends come and bring lunch and news of the world. So I will just share the standard happy selfies. With love. Who knew this #cruelintentions trio would be forever?" 13 of 16 Secret Society Meeting Sarah Michelle Gellar/Instagram The trio met up again in January 2022, celebrating nearly a quarter of a century of "secret society" meetings since they first met on the Cruel Intentions set. "24th annual meeting of the Secret Society. Everybody does it… it's just that nobody talks about it. EXCEPT ME!" Kumble captioned photos of the visit, referencing lines from the movie. 14 of 16 Group Hug sarahmgellar/Instagram The girls snapped a photo in a group hug with Shannen Doherty in March 2020. 15 of 16 Mask Up Selma Blair and Sarah Michelle Gellar. sarah michelle gellar/instagram Even the COVID-19 pandemic couldn't keep these two ladies from sharing a (masked) smooch. 16 of 16 Art Imitates Life selmablair/Instagram In a selfie posted in honor of Gellar's birthday in April 2022, the pair posed in front of a painting of their iconic Cruel Intentions scene. Blair wrote of her friend, "Happy birthday SMG. I love you forever and have since we met."