When the romantic drama Cruel Intentions premiered in 1999,
Ryan Phillippe was in his 20s. Not surprisingly, the incredibly
good-looking actor with curly hair became a crush for thousands of girls around the world.
It was 100% clear that such a talented and handsome young man has a bright future not
only in terms of career, but also in terms of his dating life. Hardly did we know how intense
things would become for Philllippe. By intense we mean marrying and becoming a dad in his early 20s,
painful breakup followed by a series of relationships,
one which would weirdly end in a 1 million dollar lawsuit against the actor.
What we totally wouldn't expect then, is that at 46, the hunky actor would remain single.
Why did that happen? Is that by choice or by chance?
Today we take a look into all the things that went awkwardly wrong with Ryan Phillippe's dating life.
Before we continue, subscribe to Rumour Juice Youtube channel not to miss
exciting stories about your favorite celebrities.
Not many actors can boast of making it big with their first role. But Phillippe can. In 1992,
One Life to Live executive producer hired a fresh-faced 17-year-old actor to play the
newly created role. Ryan's character was the first gay teenager of a daytime soap opera.
The young actor was warned against playing such a risky part, and he initially had doubts about
starting his career like that. Let us admit it: 90s were not particularly famous for their
tolerance and awareness in relation to the LGBT community. But despite all the possible risks,
young Ryan decided that he wanted to leave a positive impact by playing the
complex closeted high school junior who is a jock that becomes class president.
Soon, Ryan started getting more and more offers. It would be unfair to ignore that
in addition to demonstrating great acting skills, the young star had a very peculiar and attractive
appearance that couldn't go unnoticed. Not surprisingly, by the release of Cruel
Intentions girls just went crazy over Phillippe, who portrayed a cynical manipulative man Sebastian
who changed under the influence of true love of Annette portrayed by Reese Witherspoon.
Their on-screen chemistry was not accidental, since by that time of
filming two were already dating. Which leads us to the beginning of this love story.
The young actors actually met before they co-starred in the famous teen drama. It
happened at Witherspoon's 21st birthday party. As soon as Reese saw Ryan, she said: I think you’re
my birthday present.’ And that turned out sort of true. Just one year after they met, the two became
engaged. Before walking down the aisle, though, Witherspoon got pregnant with their first child.
Witherspoon was extremely nervous about motherhood as it was an unexpected pregnancy. But the
two perfectly nailed it together and already 4 years later another baby appeared in the family.
Witherspoon gives lots of credits to her husband saying he was a much cooler parent
than her. Ryan's mother used to run a day-care center, so he learned how to professionally
change a diaper within just five seconds. In the meantime, Witherspoon felt like she went
through a crash course in motherhood. Indeed! But it would be fair to say that both of them
went through a crash course of juggling everything all at once. Remember: they had to combine raising
two children and running successful film careers while still being in their twenties!
Speaking of careers… While in the 90s Phillippe was arguably a bigger star in their family.
After the release of Legally Blonde, Witherspoon apparently
started getting more recognition and receiving larger paychecks. In 2002,
Phillippe even made a joke while presenting an Oscar together with his wife. He said that it
was Reese who should announce the winner all by herself, because she makes more money than him.
So, when thinking of the reasons behind their split several years later, many
started questioning if there was some jealousy that affected their relationship. In 2007, they
got divorced filing the classic "irreconcilable differences" as the reason for their separation.
There were various versions explaining what happened between the two, like the one involving
jealousy, or the unconfirmed rumours of Philippe having an affair with actress Abbie Cornish, but
both revealed years later in separate interviews that the real problem was their age. Yep,
as complicated and at the same time as simple as that: they were too young when they got married.
Philippe took the divorce really hard, he characterized that period as (quote)
"the darkest, saddest place I had ever been.”
“There were a good four or five months of not being able to get out of bed.
It was the worst time in my life.”
Here we should also recall how the Hollywood hunk candidly confessed
in one of his interviews that he had been struggling with depression since childhood.
"Depression has been a huge obstacle for me ever since I was a child.
As you get older I think it decreases some, but I'm just innately kind of a sad person."
Despite that very dark period in his life probably fuelled by depression, some time
later Ryan started dating Abbie Cornish and their relationship continued for several years.
Following months of tabloid speculation that Phillippe was unfaithful to Cornish,
regularly hitting the nightclubs and being linked to other women, they broke up. When asked about
the cause of their break-up and the cheating rumours Ryan's representative simply replied:
"No comment". A representative for Phillippe maintained that it was Ryan who ended the
relationship and asked Cornish to move out of his house. While some sources said
that Cornish got tired of his non-stop partying and decided to leave for good.
After their split, Ryan had a summer fling with then 21-year-old actress and model Alexis Knapp,
who gave birth to her first and Ryan’s third child. And then there was a relationship with
girlfriend and eventually fiancee Paulina Slagter, however, they broke off the engagement in 2016.
Now, Phillippe's latest known romance, with 21-year-old Playboy model Elsie Hewitt,
ended in turmoil. She filed a $1 million lawsuit accusing the actor of beating her up
over the July 4 holiday. According to Hewitt, drunk Phillippe assaulted her and threw her
down some stairs. Phillippe's side insisted that Hewitt herself instigated the incident,
showing up to the actor’s home “under the influence” and physically attacking him.
Then, according to them, she fell and hurt herself.
Phillippe expressed his utter disgust over the allegations saying:
"As a man, raised by women, in a household where women's rights,
feminism and advocacy were very much at the forefront, I am sickened that my name can
be found in any article where domestic violence of any kind is being alleged."
Eventually, Phillippe somehow managed to reach a
settlement with his ex just days before a trial was set to start.
Now, at 46 Ryan is still a dreamboat, but it seems like following his numerous failed relationships
and an exhausting lawsuit, the Shooter star prefers to stay single. He works out a lot,
based on his recent quarantine pics. Workouts keep Ryan healthy, energetic and… busy.
Probably, he doesn't have time for new love, or he simply doesn't want to get burned again.
Phillippe is also back on track in terms of acting after quite a lengthy break.
Ryan has been working on a slew of projects for both the big screen and the small screen. His
recent works include an episode of the Will and Grace reboot in which he played himself. He also
starred in the film, The Sound of Philadelphia which is currently in post-production.
He doesn't seem to lack love in his life, since he is super close with his kids.
And if you look at his son - the boy is literally his dad's look-alike. Phillippe prefers to spend
as much time as possible with his children. It is really amazing how Ryan and Reese have managed
to develop such a successful co-parenting system despite having a complicated past.
Even though neither Phillippe, nor Witherspoon speak about their current relationship,
we remember how the actress mentioned a few years ago she'd never regretted marrying Ryan.
"I learned a lot, though. It was an excellent opportunity for me to really find out what it
means to be a partner and to be in a marriage and it’s not anything that I thought it was."
Unlike her ex, Reese re-married in 2011. Her relationship with husband,
Hollywood talent agent Jim Toth is going strong. The two support each other in everything they do.
Reese feels lucky to have him in her life. She shared in one of her interviews:
"Jim said ‘I’m gonna show you every day what a good partner is, what a good person is. I’m
going to take care of you. I’m gonna do this so much that you’re gonna get used to it.
I was like ‘What are you talking about?’ I’ve never had anybody like that in my life."
Some still regret that Phillippe didn't become THAT VERY person for Reese. Let us admit it:
they looked amazing together and we miss their beautiful couple a little. But we also
hope that Ryan will find someone who he will eventually be able to call his true soulmate.