Ryan Phillippe and Reese Witherspoon were one of Hollywood's most beloved couples in the late '90s, but they split in 2006. The split was not pretty, but their relationship is better these days.
"It's gotten to a place where we're great friends and great co-parents...," he told Howard Stern in 2011. "After I had my breakup, she called, and after she did, I called . . . I trust her to make the right decisions around our children. I hope she feels the same way."
Ryan Philippe and Rihanna reportedly hooked up for a short time in 2011, though it appears it was more of a fling than a relationship.
"They initially hooked up when things were strained with [Rihanna's ex] Matt Kemp back in early December," a source told E! of their hookup in February 2011. "She thinks he's hot. They totally had sex. And it wasn't even the first time!"
Phillippe dated Les Miserables star Amanda Seyfried from 2010 to 2011, but it ended because Seyfried wasn't comfortable with all the attention.
"When I was with Ryan, people followed me so much more, and that's probably one of the reasons that I'm not looking to date someone who's famous now," she told Glamour in 2012.
Demi Lovato was briefly linked to Phillippe in 2011. However, things cooled when 18-year-old Lovato learned about his new daughter.
"It was really hot and heavy for a while," a source told E! News, "until it basically happened. It kind of threw her for a loop."
Ryan Phillippe and Pitch Perfect star Alexis Knapp had a fling in 2010. It quickly ended, but Knapp ended up pregnant. Phillippe initially denied he was the father, but a paternity test confirmed it.
"She looks like moi. A lot more so now," Knapp told E! News of their daughter, Kailani. "They always come out looking like the dads, because men are just fat and puffy and can't open their eyes too much."
Phillippe was reportedly spotted with Cameron Diaz in 2011.
"Cameron and Ryan are getting to know one another," a source told InTouch Weekly. "She wants to settle down, and she likes that he's a single dad so she's open to the idea of seeing where things go with him."
The relationship never went anywhere.
Phillippe's first serious relationship post-Witherspoon was with his Stop-Loss co-star, Abbie Cornish. Their relationship abruptly ended in 2010.
"I have a new rule: not to date anyone who has a publicist," he told Howard Stern in 2011 of their split. "Who announces a breakup? I don't understand that!"
Reed wasn't the only young celeb Phillippe was spotted with. He reportedly had a fun time with Lindsay Lohan for a brief time in 2007.
"They definitely hooked up," a source told US Weekly. "It was the first time." However, she wasn't that into him. "Lindsay's not really into him," the source added. "But obviously she loves the drama. She thinks he's hot!"
Phillippe was reportedly spotted out at L.A. hostpot Winston's with then 18-year-old Nikki Reed in 2007. He later denied the rumors by saying that "I'm not a perfect person. (But) I'm not guilty of a lot of things I have been accused of."