At 16, an up-and-coming Reese Witherspoon generates buzz after accompanying Chris O'Donnell to a tribute party for his Scent of a Woman costar Al Pacino in February 1993. Though the actress flew to New York from her native Nashville to attend the soiree with the 22-year-old actor, the pair keeps mum about their relationship, with the actor's rep telling PEOPLE, "Chris really likes her, [but] they're just friends."
After meeting at a club in 1991, Witherspoon admits to crushing on actor Stephen Dorff. "He's very charming and disarming, he can just have you completely reeled in," a young Witherspoon told Details magazine of the Hollywood bad boy in 1995. Though they're spotted together at the premieres of Demolition Man and Backbeat, Witherspoon adamantly denies dating her S.F.W. costar. "I wouldn't date Dorff for all the money in the world," she said, adding, "You have to be comfortable giving him space. I'm not that kind of girl."
Witherspoon moves from one bad boy to the next, starring as the object of Mark Wahlberg's obsession in Fear. A fan of the former Calvin Klein underwear model's, ahem, body of work, Witherspoon's onscreen chemistry with Wahlberg seems to resonate offscreen, with the costars being linked through the filming of the sexy thriller in 1995.
Once Hollywood's golden couple, Witherspoon and Phillippe first met on the set of Cruel Intentions before getting hitched in 1999. The pair, who had been together for close to a decade, both agreed that their 2006 divorce was the hardest thing they had experienced. "I spent a few years just trying to feel better ... You can't really be creative when you feel like your brain is scrambled eggs," Witherspoon has said.
Picking up the pieces, Witherspoon moves on from her heartbreak with actor Jake Gyllenhaal, her costar in the 2007 CIA thriller Rendition. "He's very supportive," the actress said of her then-boyfriend, with whom she spends low-key weekends at her Ojai, Calif., farmhouse. But after two years together, they split in November 2009. "Jake would marry [Reese] tomorrow, but Reese doesn't want to go there yet," a friend of the pair told PEOPLE.
After a year-long, whirlwind romance with Hollywood agent Jim Toth, 40, Witherspoon, who just turned 35, is finally ready to give marriage another shot. "Jim knows Reese is the one for him," a pal of Toth's told PEOPLE, while a source close to Witherspoon adds, "She knew where she wanted to go and moved fast. It was impressive."