The two were romantically linked in 1993 after the actress, then 16 years old, accompanied the then-22-year-old actor to a tribute party for his Scent of a Woman co-star Al Pacino in New York City. Neither Reese nor Chris ever confirmed a relationship.
The two starred in the 1994 movie S.F.W. (which stands for "So F--king What") and sparked dating rumors in the early '90s. "I wouldn't date Dorff for all the money in the world," Reese told Details magazine in 1995. "I really admire the girls who do hold Dorff's attention. I don't know if it's because he doesn't know what he wants, or that he knows exactly what he wants and if that person doesn't apply, he's going to find it somewhere else. You have to be comfortable giving him space. I'm not that kind of girl."
Mark and Reese sparked romance rumors after showcasing chemistry in the 1995 thriller Fear. Neither has ever confirmed a relationship.
The two co-starred in the 2007 thriller Rendition and dated for two years before they split in 2009.
"He's very supportive," Reese told Vogue in 2008. "Suffice it to say, I'm very happy in life, and I'm very lucky to have a lot of really supportive people around me who care very much for me, and, you know, that's all you can hope for in life. I am very blessed in that way."
Despite popular belief, the two did not meet on the set of the 1999 film Cruel Intentions, in which they played love interests. Reese and Ryan actually first met when he crashed her 21st birthday party in 1997, weeks before the actor got the script for the movie. The two kept in touch after the bash and he immediately passed the screenplay to her after he received it, according to Pennsylvania newspaper The Morning Call.
"I crashed her party," Ryan told the outlet in 1999. "I went with a friend because I knew there would be free food and drinks. I was just sitting back in the corner pounding away the drinks when somebody walked over and introduced Reese to me."
Reese told Jane magazine in 1998, "I don't know what came over me—maybe the seven Midori sours—but I told him, 'I think you're my birthday present.' He thought it was so flattering, and now that I think about it...how embarrassing!"
The two wed in June 1999, three months after the release of Cruel Intentions, and are parents to daughter Ava Phillippe, born in 1999, and Deacon Phillippe, born in 2003. Reese and Ryan finalized their divorce in 2008.
Reese and Jim, a CAA talent agent, tied the knot in 2011 after dating for a year. The two welcomed son Tennessee Toth in 2012 and are still happily married.