Ryan Phillippe rose to fame in 1992 for his role in ABC drama, One Life To Live, where he played Billy Douglas - the first gay teenager on a daytime soap opera.
After leaving the show in 1993, he went on to star in various TV shows before getting his big break in 1997 horror movie, I Know What You Did Last Summer.
He met his soon-to-be ex-wife Reese Witherspoon before they starred in Cruel Intentions together in 1999 but why did the couple get divorced and who has Ryan been in a relationship with since?
Here's everything you need to know about Phillippe's dating history:
Reese Witherspoon
Ryan met Legally Blonde actress Reese at her 21st birthday party in 1997.
The pair soon hit it off and they tied the knot in 1999 just weeks after the release of Cruel Intentions.
They were together for seven years and had two children together - Ava and Deacon - before they split in 2006.
When news broke of the split, Ryan was accused of cheating on his wife with Stop-Loss co-star Abbie Cornish, which he denied.
He said in a statement in November 2006: “I’m not a perfect person, but I’m not guilty of a lot of the things I have been accused of. My priority is and always has been the health and safety of my family."
Commenting on the split in 2014, Reese Witherspoon said on 60 Minutes: “Phew, that was a tough year that followed. I got divorced the next year and I spent a few years just trying to feel better.
“You know, you can’t really be very creative when you feel like your brain is scrambled eggs. I was just kind of floundering career-wise cause I wasn’t making things I was passionate about, I was just kinda working. It was really clear the audiences weren’t responding to anything I was putting out there.”
Abbie Cornish
Following his split from Reese, Ryan went on to date actress Abbie for around four years before their bitter split in 2010.
The split followed months of tabloid speculation that Ryan has been unfaithful as he was regularly seen in nightclubs and being linked to other women.
A spokesperson for Abbie said to People at the time: "Abbie ended the relationship with Ryan and she moved out of their home."
Alexis Knapp
After rumoured flings with the likes of actress Lindsay Lohan and model Jessica White, Ryan met Pitch Perfect star Alexis Knapp.
The pair had a brief relationship in mid-2010 but they split up suddenly in the September.
The actress fell pregnant just before the split and at the time, there was speculation that Ryan was not the father.
The actor allowed his ex-girlfriend to name the baby girl Kaliana Phillippe-Knapp, following the birth in 2011 despite questions surrounding the paternity of the child.
However, the former couple then took a DNA test and proved that Ryan was in fact the baby's father.
Amanda Seyfried
Following his split from Alexis, Ryan went on to date Mamma Mia and Mean Girls actress Amanda Seyfried.
The pair had an on/off relationship and Amanda stood by her ex when it was revealed that he was the father of Alexis' baby.
The pair then officially split after seven months of dating in June 2011.
"It was mutual," a source told Us Weekly. "They were never fully committed."
Paulina Slagter
Following alleged brief flings with Demi Lovato, Rihanna and Ashley Greene, Ryan moved on with lawyer and former model Paulina Slagter.
The pair got engaged in 2011 but after a five year engagement, the pair called it quits in 2016.
TMZ claimed at the time that Paulina filed an 'Annoying or Harassing Electronics Communications Harassment Report' with the LAPD in March 2017 after Ryan reportedly sent her angry texts.
The then-26-year-old said the actor sent her a slew of 'aggressive and extremely angry' texts after their break-up, according to Daily Mail.
Law enforcement sources reportedly told TMZ at the time that Paulina dropped the case shortly after the report was filed as she "didn't want the publicity".
Elsie Hewitt
Following the end of his relationship with Paulina, Ryan met Playboy model Elsie Hewitt and they soon embarked on a four-month romance.
However, the relationship came to an end in July 4 and Elsie pressed charges against Ryan for alleged assault.
The alleged attack occurred on July 4, 2017, when the model went to Ryan's house to pick up her things after their relationship had ended.
The model claimed that the then-43-year-old actor threw her down the stairs during alleged attack after he shouted: "Get the f*** out of my house you crazy c***."
Elsie claimed she was left with "chest pain, severe bruising and abrasions" from the alleged altercation.
In her $1 million (£902,000) lawsuit report, which was obtained by People magazine, the model claimed Ryan was drunk when she arrived at his property, and that he frequently abused alcohol and both legal and illegal drugs.
The complaint claimed: “He grabbed Hewitt's upper arm so violently that his grip left heavy bruises on her arm hours later.
"He then braced his body and violently threw her down the staircase as hard as he could.”
The documents went on to allege: "When Hewitt finally made it back to the top of the second staircase to pick up her belongings, Phillippe repeatedly grabbed Hewitt, struck her, cornered her, kicked her, and aggressively pushed her to the ground."
A source close to Ryan told E! News at the time that "there is no restraining order presently in force of any kind" and that there was an emergency protective order, but it was terminated a few days after the alleged attack.
In November 2017, Ryan's attorney denied Elsie's allegations, saying that they were "utterly false" and an "unjustified attempt to extort money from Phillippe, and to gain publicity for herself and her modeling career."
Two years after the alleged incident, a notice of a settlement between Ryan and ex-girlfriend Elsie over her $1m lawsuit for alleged assault was filed at a Los Angeles court.
Since his split from Elsie, Ryan has kept his love life private and is yet to announce whether he is dating again following the lawsuit.
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