Ryan Phillippe’s failed marriage with Reese Witherspoon is no more new. But not everyone knows about his past romantic involvements.
With that, fans have been lately wondering about Ryan Phillippe’s dating history. These days, the Big Sky actor is ruling the internet as he shared his pictures with his daughter, Kai, following a happening Thanksgiving weekend.
Everyone knows Ryan Phillippe. Such is his pro prominence, made through immense hard work and dedication. Being his fan, you must have watched- I Know What You Did Last Summer. If not, you are missing out on one of his best performances. Hailing from New Castle, he is now 49 years old.
In case you are looking for some of Ryan Phillippe’s greatest acting hits, make sure you watch- The Locksmith, American Murderer, Damages, Flags of Our Fathers, MacGruber, and Shooter. Did you not watch Secrets and Lies? We saw Ryan portraying the leading role of Ben Crawford in Season 1 of the same.
Besides acting, Ryan Phillippe also appeared in some music videos. For this, he worked with artists like- OutKast, 100 gecs, etc.
Moving on to Ryan Phillippe’s ex-girlfriends, one of the notable ones is Reese Witherspoon. After all, they were married for a long time. Right after his divorce, he dated many from the industry itself.
Concerning her daughter, Kai, mentioned at the beginning, the actor shares her with Alexis Knapp. So, who were the other ones? Here is what we know about Ryan Phillippe’s dating history.
Ryan Phillippe’s Dating History: Meet His Ex-Lovers
Talking about Ryan Phillippe’s dating history, Reese Witherspoon makes it first on the list. Who doesn’t know her? Reese is a globally known actress from New Orleans. Did you watch – Your Place or Mine? She played the character of Debbie Dunne.
It was on Reese’s 21st birthday bash in 1997 when the pair met. There was a quick spark between Ryan and Reese, and they hardly took time to decide on their marriage. Their wedding ceremony took place at Old Wide Awake Plantation in South Carolina.
With her, the Big Sky actor shares a couple of children- Ava (daughter) and Deacon (son), respectively. After spending several years together, they called it quits in 2006. What was the reason?
One must note that it was Reese who took the initiative and filed for a divorce. The Morning Show star cited the reason for having “irreconcilable differences.” At present, they share joint custody of their children. Even though their divorce was finalized in the following year, they came out with the revelations of her feelings later.
Concerning her divorce from Ryan Phillippe, Reese addressed it as having felt “very out of control.” Despite their separation, the two are very much in touch, mainly for the sake of their children. Also, neither of them sought any spousal support during their divorce settlement.
Now comes – Abbie Cornish. Another brilliant actress, but from Lochinvar, New South Wales. She rose to fame for her portrayal of Heidi in Lochinvar, New South Wales.
Regarding her acting, the credits go to Candy, Bright Star, Blackout, and Marking Time. How can we forget to mention Jack Ryan? Considering you are one of her fans, because of her performance as Cathy Mueller, it’s highly recommended to you.
Not everyone knows that Abbie Cornish is also a great singer. Yes! You should listen to her 2021 song – “I’ll Be There For You.”
Moving on with Ryan Phillippe’s relationship with Abbie Cornish, it all started in 2006. That was right after the actor’s divorce from Reese. Where did they meet? It was on the set of Stop-Loss.
Ryan Phillippe and Abbie Cornish dated each other for four long years, ending in 2010. The latter reportedly called him to end their affair. What was the reason? Nothing about it was publicized. But a source close to the pair shared that Ryan didn’t take it as seriously as she did. That caused the rift between the two. Also, she was tired of his partying habits.
As mentioned above, Alexis Knapp, Ryan Phillippe’s relationship with her was short-lived. To be more particular, it lasted for just four months. To the newbies wondering about Alexis Knapp, she is a versatile actress known for Stacie Conrad in the film series Pitch Perfect. She made her acting debut in 2009.
Are you looking for some of Alexis Knapp’s acting works? In that case, you must watch – Project X, The Anomaly, The Orville, and Ground Floor Season 1.
Ryan Phillippe and Alexis Knapp started sharing a romance in mid 2010. But they were done as a couple by September of the same year. Why did they split? It’s not revealed to the public yet.
After their separation, The Orville actress found herself pregnant, sharing the baby with her then ex- Ryan. In 2011, she welcomed Kai, whom both of them are co-parenting now, romantically despite living apart from each other.
While discussing Ryan Phillippe’s dating history, Amanda Seyfried makes it to the list. Who is she? Well, her ex-girlfriend Amanda started her modeling career at the age of 11. She made her acting debut after four years. She rose to fame for her portrayal in Mean Girls. Also, her performance in Big Love was highly appreciated.
Coming back to Ryan Phillippe’s relationship with Amanda Seyfried, it all started in 2010 and continued for a few months. They met each other for the first time at Kate Hudson’s Halloween party. During their course of romance, the actor used to put her off going out with other celebs.
Their break up was mutual. Amanda and Ryan were never very serious about their affair. In other words, even though it lasted just for a few months, it was on and off. To be more precise, they were done as a couple by June 2011. Despite their split, Ryan Phillippe is believed to be on good terms with Amanda Seyfried. Not all relationships end in a bad way.
What! Yes! Ryan Phillippe also shared a brief romance with the Rude Boy singer Rihanna. The singer doesn’t need any dramatic introduction. While we discuss her, it would be wrong if we don’t mention her all-time hits. One must listen to Diamonds, Don’t Stop the Music, We Found Love, Only Girl, and Needed Me.
Talking about Ryan Phillippe’s dating history with Rihanna, it was never serious but more like a fling. It was in December 2010 that the two reportedly hooked up. Both kept it pretty much low-key. According to Rihanna, he always looked hot and stunning, and that’s what was reported.
Several rumors sparked, stating the two had hooked up when Rihanna had relationship issues with Matt Kemp. The alleged couple met at a charity event, and there was no PDA. When asked to Amanda, she even denied Rihanna’s story.
After several years, more precisely in 2017, Ryan Phillippe opened up about her willingness to work with Rihanna. He wanted to work on a film with her. Well, the Diamonds singer didn’t pass any comment regarding their hook-up news.
Rihanna was not the only one. Ryan Phillippe also sparked hook-up rumors with the Tell Me You Love Me singer. Yes, we are talking about Demi Lovato. She has a mind-blowing music career. Some of Demi’s notable works are- Unbroken, Give Your Heart a Break, Commander in Chief, Cool for the Summer, etc. Which is your favorite?
Very little is known about Ryan Phillippe’s relationship with Demi Lovato. It was brief, starting in July 2011. Both kept it low, and there was never any seriousness. From the singer’s perspective, she had just stopped seeing Joe Jonas at the time. The former couple sparked relationship rumors after Ryan was spotted coming to her home in Los Angeles.
Talking about Ryan Phillippe’s dating history, Ashley Greene was also one of his ex-girlfriends. Who is she? Well, Ashley is an actress from Jacksonville, Florida. She gained massive recognition for playing Alice Cullen in the Twilight series. You should also watch how brilliantly she performed in Rogue and The Retirement Plan.
It was in 2013 that Ryan and Ashley started sharing a romance. They met each other on the set of One Shot. At that time, Ashley felt like she was too young to be in a serious relationship. Things were casual. The blonde beauty said, “I’ve always been in relationships. And I knew I needed to learn to be comfortable alone.” They dated for a year.
How can we forget to mention Paulina Slagter? Ryan Phillippe didn’t just date but also reportedly gotten engaged to her. Who is she? Well, Paulina is professionally a lawyer. However, she did some part-time modeling work in her teenage years. Did you watch Entourage? She also played a minor role in that.
Talking more about Paulina Slagter, besides the entertainment industry, she advised her clients about merger reviews, congressional investigations, and many more.
Ryan Phillippe and Paulina Slagter met each other in February 2012. Just after three months or so, the two made their red carpet appearance together as a couple at a Hugo Boss event in China. The Big Sky actor popped the question to the model in December 2015.
During an interview, Ryan was asked about her then-fiancee. The actor didn’t fail to gush her, saying, “She is awesome.” Sadly, after five years of togetherness, the two called it off. Fans were left in shock as they expected the two to tie the knot. Why? Ryan allegedly accused her of cheating. On the other hand, Paulina didn’t like to get much attention from the public. Both had expectations from life, which probably made them apart.
Ryan Phillippe’s relationship with Elsie Hewitt also caused many headlines. What’s her identity? Elsie is a model who started her career at the age of 18. One must note that she is recognized for the 2018 Spring/Summer Guess Campaign. Besides this, she also did a few acting works such as Teenage Badass, Turnt, and Mostly Ghostly: Have You Met My Ghoulfriend? Etc.
Their romance lasted for just a couple of months- short-lived. Why did they part their ways? It was Elsie who accused him of domestic violence at his California home. She filed a $1 million lawsuit against him. It was also reported that Elsie stayed hospitalized at Cedars-Sinai Medical Center in Los Angeles.
Were the allegations made against Ryan Phillippe true? He denied it, stating that he was “devastated.”
Best Wishes to Ryan Phillippe for the upcoming days. Make sure to follow the Big Sky actor on his Instagram account for more updates.