The Complete List of Ryan Phillippe's Rumored A-List Ladies

by SheKnows
Sep 20, 2017 at 2:30 p.m. ET

For being a pretty big star, Ryan Phillippe manages to keep most of his love life low-profile. Sure, his dating life will pop up in a headline or two every now and again, but considering how famous he is, he does a pretty good job of keeping his private life private.

But just because we're not constantly hearing about it, doesn't mean he's not dating. Yup, Phillippe has managed to rack up a pretty impressive list of A-List women that he's rumored to have dated (or at least have a fling with). Not super surprising, considering those baby blues of his.

Though his daughters Ava Phillipe and Kai Knapp are most likely his No. 1 ladies always and forever, the following group might have earned a place in his heart at one point or another, however brief it might have been. 

Originally posted September 2013. Updated September 2017.

1 /12: Elsie Hewitt

1/12 :Elsie Hewitt

So Phillippe's most recent relationship is not turning out to have such a happy ending.

His ex Elsie Hewitt, who dated from April 2017 until July, filed a civil lawsuit this week alleging that Phillippe had gotten violent and assaulted her during a fight back in July. Phillippe's camp alleges that Hewitt was the aggressor and is planning a countersuit

2/12 :Katy Perry

In spring 2017, rumors ran wild that Perry and Phillippe were a hot item, but both parties adamantly denied involvement. 


3 /12: Reese Witherspoon

3/12 :Reese Witherspoon

Ryan Phillippe and Reese Witherspoon were one of Hollywood's most beloved couples in the late '90s, but they split in 2006. The parting of ways 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. "I trust her to make the right decisions around our children. I hope she feels the same way."

4 /12: Abbie Cornish

4/12 :Abbie Cornish

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!"

5/12 :Nikki Reed

Phillippe was reportedly spotted out at L.A. hostpot Winston's with then 18-year-old Nikki Reed in 2007. He later kinda denied that he was dating her by saying, "I'm not a perfect person. (But) I'm not guilty of a lot of things I have been accused of."

6 /12: Lindsay Lohan

6/12 :Lindsay Lohan

Reed wasn't the only young celeb Phillippe was spotted with. He reportedly had a fun with Lindsay Lohan for a brief time in 2007.

"They definitely hooked up," a source told US Weekly via PopSugar. "It was the first time... Lindsay's not really into him," the source added. "But obviously she loves the drama. She thinks he's hot!"

7/12 :Alexis Knapp

Ryan Phillippe and Pitch Perfect star Alexis Knapp had a fling in 2010. It quickly ended, but not before Knapp conceived their daughter, Kailani Knapp. 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. "They always come out looking like the dads, because men are just fat and puffy and can't open their eyes too much."

8/12 :Rihanna

Philippe and Rihanna reportedly hooked up for a short time in 2011, though it appears it was more of a fling than a relationship.

"She thinks he's hot. They totally had sex. And it wasn't even the first time!" an Us Weekly source claimed at the time. 

9/12 :Demi Lovato

Demi Lovato was briefly linked to Phillippe in 2011. However, supposedly things cooled when Lovato learned that Phillippe had a baby 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."

10 /12: Cameron Diaz

10/12 :Cameron Diaz

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." 

11 /12: Amanda Seyfried

11/12 :Amanda Seyfried

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.

12 /12: Ashley Greene

12/12 :Ashley Greene

Not a whole lot of info on how involved Greene and Phillippe got, but the pair definitely got people talking after they were spotted leaving L.A.'s Vignette Lounge together in March 2013.