Actor Ryan Phillippe Consecutively Failed Relationship With Wife And Girlfriend; Added By His Kid's Fame

Only rare people have successful relationships, and they guess Ryan Phillippe is not one of them. After strings of failed relationships, Ryan Phillippe, an American writer, actor, as well as director, is single but not alone.

Ryan has his kids, and they have only added to Ryan’s fame, all thanks to his daughter. But what about Ryan’s failed relationships?

Young Love That Ended Soon But Mutually!

Ryan Phillippe met Reese Witherspoon, an American actor, as well as a producer back on Reese’s 21^st birthday. Upon meeting Witherspoon, Phillippe did spend all night talking to her, while Witherspoon said, 

"I met him at my 21st birthday party. I don't know what came over me - maybe the seven Midori sours."

Ryan Phillippe and his wife Reese Witherspoon back when they were in a relationship (Photo: usmagazine.com)

The couple started dating and engaged in December of 1998. Following their relationship, the couple married in South Carolina at Old Wide Awake Plantation near Charleston on June 5, 1999, following the release of their hit film, “Cruel Intentions.” Resse was six months pregnant when their marriage ceremony happened.

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Ryan proposed to Reese in December of 1998 at The Planter's Inn in Charleston, South Carolina, when the couple was on vacation. The ring he offered her with was a scarce early 1990s Neil Lane, four-carat Asscher-cut-diamond platinum ring.

Witherspoon gave birth to two kids, daughter Ava and three months later, and the couple’s Son Deacon joined the family in 2003.

Reese Witherspoon along with her daughter, Ava, and son, Deacon takes a walk in Santa Monica, California on Saturday 12th July 2014 (Photo: dailymail.co.uk)

Alas! Their relationship could only last for seven years as Resse Witherspoon, and Ryan Phillippe separated on 30 October 2006. A reporter for the couple said in a statement released:

“We are saddened to announce that Reese and Ryan have decided to separate formally, they remain committed to their family, and we ask that you, please respect their privacy and the safety of their children at this time.”

In 2007, a petition was filed by Ryan Phillippe requesting equal visitation rights as well as joint legal and physical custody of their children. Ryan Phillippe said that age is the reason behind their divorce to Larry King in 2015.

"I think more of the problem was age. When we got together, we were so young."

Moreover, he added,

"I think it can create issues with two people in this industry because there's so much noise that goes along with it."

Reese Witherspoon then went on to marry agent Jim Toth on 26 March 2011, following their divorce in California. 

Series Of Failed Relationships!

After two years of split, Ryan was seen with his Stop-Loss co-star Abbie Cornish in 2008 Australian in Film Breakthrough Awards, which was also their first major event as a couple. The couple dated in 2007.

Both of them split in February 2010 after there were rumors that Phillippe's habit of regularly hitting the nightclubs and being linked to other women was the main reason for the couple to split.

Phillippe subsequently dated actress as well as model Alexis Knapp in the summer of 2010 and split in September of 2010. After their breakup in September, Phillippe's ex-girlfriend Knapp said that she was pregnant with Reese’s baby and gave birth to their daughter, Kailani Merizalde Phillippe-Knapp, on 1 July 2011.

Ryan Phillippe spotted with Elsie Hewitt pre-2019 (Photo: eonline.com) 

Ryan Phillippe started dating Paulina Slagter in 2012. The actor, Phillippe 45, and the law school graduate, 27, got engaged in 2015 Christmas after dating for five years. Ryan Phillippe split from his fiancée Paulina Slagter only ten months after popping the question. The reason behind their breakup was unknown.

However, the co-writer did not stop there; he was into big legal trouble in 2017 when he dated model Elsie Hewitt. The playboy model accused him of assault and sued him with a $1 million Physical Assault Lawsuit. According to the legal documents, Elsie blamed him for kicking her, punching her and throwing her down a flight of stairs when she went to his house to collect her belongings.

Following the same, the couple created a lot of buzz in media. Interestingly, Ryan denied the accusation of the assault and explained he had not done anything, as explained by his ex. He also added; he just wanted her to leave his house and lifted her like a child to take her out of the house.

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But, much to his surprise, the model leaked pictures of the injuries she inflicted during the assault and made it public on the news in September 2017. Now, two years down the line, the case was due to come before a judge, but the two settled on an agreement in October 2019. 

After staying in a relationship for four months, the couple had been involved in the incident. All in all, the case is finally at rest, and both the parties are back on their normal lives.

Amazed By Daughter's Fame!

Ryan Phillippe along with her daughter, Ava Phillippe in an afternoon meeting in August 2015 (Photo: dailymail.co.uk)

Ryan Phillippe and Resse Witherspoon’s daughter Ava Phillippe is already a star, thanks to her social media. Ava’s dad Ryan also opened up about how he handles his daughter’s Instagram fame as well as how Ryan feels about her having 228,000 followers.

“Well, she has an incredibly famous mother and a moderately famous father, but that’s how that works and also social media is largely driven by the youth and the associations made within that group. She’s incredibly talented.”

On the other hand, Ryan himself made an appearance in ABC daytime drama One Life to Live where he played the character of Billy Douglas from 1992 to 1993, which was the first gay teenager on a daytime soap opera. The show was also controversial due to gay scenes back then. Being an actor as well as a writer, Ryan has net worth as that of $30 million.