20 Rare Photos Of Reese Witherspoon And Her Ex Ryan Phillippe

All ‘90s kids will remember the time that Reese Witherspoon and Ryan Phillippe were the couple of the moment. The angelic couple made fans believe that true love does exist after they started dating in the late ‘90s while both of them were two of the biggest teenage stars around.

Shortly after becoming romantic, the pair played onscreen lovers in the iconic movie about less-than-nice Intentions, which made fans fall in love with them as a couple even more. Needless to say, fans were thrilled when Reese and Ryan eventually tied the knot in 1999. Their daughter, Ava Elizabeth, was born the same year, while their son, Deacon, was born in 2003. At the same time, Reese’s star was on the rise. She took home the Academy Award for her portrayal of June Carter in Walk The Line in 2005. Ryan and Reese seemed to have the picture-perfect life together, and fans couldn’t have been happier for them.

However, things came crumbling down when the couple announced their divorce in 2006, surprising much of Hollywood. Although the two remain amicable for the sake of co-parenting, they’ve since moved on with other people, making this another former celebrity couple that’s no more. Take a walk down memory lane with these old photos of the iconic couple while still together.

20 Reese Was Only 23 They Got Married

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Ryan and Reese were really young when they got together. In fact, Reese was only 23-years old when they walked down the aisle and welcomed their first child together. They were married in a modest ceremony in Charleston, South Carolina was Old Wide Awake Plantation in June 1999. Their daughter Ava was born in September of the same year.

During an appearance on Lorraine a few years back, Reese was asked, “What do you do when you get to 40 and you made a decision when you were 25 to get married and have kids?” The actress replied, “I got married when I was 23 and had two kids by 27. Sometimes it’s good to know yourself.”

However, Reese added, “I would never change anything”.

19 They Admit They Weren't Ready To Have Kids

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While Reese and Ryan have never opened up about the real reason their marriage went south, both celebrities have hinted that having children young pit a strain on their relationship. From the sounds of it, the young parents didn’t know what they were getting themselves into.

“I was 23 [when I became a mom]. I didn’t know what I was doing. I was young. ... When people ask, ‘When’s the best time to get pregnant?’” Reese once explained. “I say, ‘Pick the best day for when your entire life is gonna change.’ There’s no good time to have your world turned upside down.”

18 Age Played A Part In Their Divorce

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Despite all the rumors surrounding Ryan’s involvement with Abbie Cornish, both he and Reese have given another reason as to why their relationship didn’t work out: age. On separate occasions, both actors have said that they just got together too young.

"I think more of the problem was age. When we got together we were so young," Ryan told Larry King in 2015. “I think it can create issues with two people in this industry because there's so much noise that goes along with it."

In 2017, Reese similarly said, “I got married when I was 23 and I had two kids by the time I was 27. So I don’t know, you know, sometimes it’s good to know yourself,”

17 They Didn’t Have A Pre-Nup

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When Ryan and Reese first got together, he was the bigger star of the two. However, by the time the couple announced their divorce in 2006, the tables had turned. So many fans were curious to see how the couple would divide their assets.

According to TMZ, the couple never signed a prenup, so technically all of Reese’s fortune was fair game during the divorce. The publication said Reese was earning around $20 million per movie at the time, while her husband was averaging only $2.5 million. However, in the end, Ryan didn’t end up requesting spousal support from Reese.

16 Ryan Said They Never Hooked Up Post-Divorce

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Many fans were honestly hoping for years that Ryan and Reese would get back together. Alas, that day never came. The exes have gone so out of their way to make it clear they’re not getting back together that Ryan has even quashed rumors that the two have been together since their divorce.

During a 2010 interview with Howard Stern, the host got candid when he asked Ryan if he ever hooked up with Reese after they separated. "That hasn't happened," the actor said sheepishly. We guess this is one ‘90s couple that has gone down in history for good.

15 They’ve Argued Over Ryan’s Partying

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One thing that may have been a factor in the couple’s divorce was partying. Why? Because the parents were said to still be arguing about this issue years after their divorce. In 2015, Ok Magazine reported that Reese had called out her ex for his wild habits as of recently.

A source said that Ryan was worried Reese would start keeping the kids away from him. “He explained that she is trying to cut him out of their children’s lives and that Reese complains that Ryan parties too much,” they explained. The insider added, “Reese tells him they’re busy with schoolwork.”

14 Ryan May Have Been Jealous Of Reese’s Success

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Some fans have wondered if jealousy was to blame for the couple’s divorce. Not jealousy over other people, but in the professional sense. Reese’s huge success started shortly after the couple married, while Ryan’s stayed the same. So, some fans assume his professional insecurities contributed to their marital problems.

However, in 2009, Ryan shot down the rumors. "That was the least of our problems. I was always really proud of her success,” Ryan said. “I'm not a competitive person, and I have no aspirations to be a giant in this industry. I like making movies, but I never had designs on making $25 million a picture.”

13 Reese Has Called The Divorce Embarrassing

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Divorces are already difficult in general. So imagine going through one when the entire public eye is watching you. That’s what Reese says made her separation from Ryan extremely painful. Sometimes being famous has its downfalls.

“It was very humiliating and very isolating,” she revealed in 2009, Daily Mail reports. “I’m never gonna feel any better than I feel right this minute and nothing's ever gonna make sense again. And I still have moments where I’m like, nothing's ever gonna make sense again.”

Reese concluded, “By the way, if it’s not painful, maybe it wasn’t the right decision to marry to begin with. Those are the appropriate emotions.”

12 Ryan Is Tired Of Being The Bad Guy

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Many fans feel that Reese was the victim in her divorce. The years following his divorce, the actor received a ton of bad press and negativity from fans (which some say is why his professional life became stagnant).

In 2010, Ryan opened up to Us Weekly about how sick he was of always being characterized as the bad guy. "I've been dumped on in the press for relationship stuff since Reese and I divorced,” he told the publication shortly after his break-up with Abbie, who he’d been dating since announcing his and Reese’s separation in 2006.

"I'm tired of getting [dumped] on," he said. "I don't feel like I deserve it. Things happen! How many people have you [ended relationships with] over your life?"

11 They Went Back To Each Other After Their Break-Ups

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Around the same time that Ryan separated from Abbie Cornish in 2010, Reese was going through a break-up with actor Jake Gyllenhaal after almost three years together. Fans were surprised when Ryan later admitted that the two exes turned to each other for support following their first break-ups post-divorce.

"It's gotten to a place where we're great friends and great co-parents,” Ryan explained, Us Weekly reports. "After I had my breakup, she called, and after she did, I called." Although fans at the time thought this might mean the exes were reconciling, it wasn’t long before Reese got in a relationship with her current husband, Jim Toth.

10 Ryan’s Ex-Fiancée Says He Mistreated Her

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From 2011-2016, Ryan was in a relationship with Paulina Slagter, with the two even becoming engaged at one point. However, their relationship came crumbling down amid reports that Ryan had mistreated his fiancée.

Paulina came forward about her experience with the actor, saying he mistreated her various times during their relationship. But things got really chaotic post-breakup, as she claims Ryan wouldn’t stop harassing her via text message. According to TMZ, Ryan verbally berated the model in his messages.

Although Paulina originally filed a lawsuit against her ex, a source told the publication she dropped it “shortly after filing it because she didn’t want the publicity.”

9 Reese Once Hinted Ryan Hurt Her, Too

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Although Reese has never said any bad things about her ex-husband by name, last year the celebrity did hint that she was once in a problematic relationship. Given that she said this around the exact time domestic dispute allegations were being launched at her ex, fans instantly wondered if she could be referring to him.

"A line got drawn in the sand and it got crossed, and my brain just switched and I knew it was going to be very difficult but I just couldn’t go any further,” Reese said during an interview with Oprah. “But it was profound and I was young.” On a separate occasion, the actress said that her youth was to blame for the dissolution of her marriage.

8 Ryan Is Also Having Legal Problems With His Newest Ex

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Although Ryan’s divorce from Reese might seem like the most dramatic moment in his love life, the actor is actually going through some troubles at the moment that might qualify as the most eyebrow-raising thing.

Ryan got into a relationship with model Elsie Hewitt following the end of his engagement to Paulina Slagter, whom he dated from 2011-2016. After Ryan and Elsie’s break-up last year, she made several eyebrow-raising claims against him.

In early April, she made headlines for requesting access to court documents related to any domestic disputes made against Ryan in the past, The B. reports. The model has launched a $1 million lawsuit against Ryan.

7 They Met At Reese’s 21st Birthday

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We told you these two got together young! Reese and Ryan were first introduced in 1997 at her 21st birthday party. They soon began filming the Intentions movie together, which debuted in theatres in 1999.

“I don't know what came over me — maybe the seven Midori sours — but I told [Ryan], 'I think you're my birthday present,’” Reese told Jane magazine in 1998. “He thought it was so flattering, and now that I think about it ... how embarrassing!"

The couple married in 1999, only two years after meeting. Reese was only 23, while Ryan was 25.

6 Reese Was Pregnant When They Wed

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One of the reasons it seems the couple rushed to the altar was because Reese was already several months pregnant with the couple’s first child. The couple was married in June 1999, while their daughter Ava was born in September of the same year. Their son Deacon was born in 2003.

“You have to get to that point as a divorced parent, as any parent, where you’re not putting yourself first,” Ryan has said about co-parenting, People reported. “You want the kids’ experience to be it's own and not like, ‘Well, I need to have my time!’ We have been very good about that.”

5 Their First Pregnancy Wasn’t Planned

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Given that the couple wasn’t even married when they were first expecting, it’s easy to conclude that Ryan and Reese’s first pregnancy wasn’t planned. Reese once got candid about how interesting it was to become parents unexpectedly and at such a young age.

“Ava wasn’t planned, and suddenly I was faced with the prospect of becoming a mother and I had never even held a newborn in my arms before!” She explained, Fame10 reports. “What was interesting about our becoming parents was that Ryan was the really cool one. His mother had once run a day-care center and he could change a diaper in something like five seconds flat.”

She continued, “It was amazing to see him work! I feel like I went through a crash course in motherhood.”

4 Ryan Gets On Great With Reese’s New Husband

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While many fans might assume things are awkward between Reese’s ex-husband and her new husband, it turns out that Ryan approves. Reese married talent agent Jim Toth in 2011, five years after announcing her and Ryan’s divorce. The couple welcomed a son, Tennessee James, in 2012.

It sounds like there’s no beef between Ryan and Jim. In fact, Ryan has only had kind things to say about the new man in Reese’s life. "I trust her to make the right decisions around our children," he told Us Weekly when Jim and Reese first started dating. "I hope she feels the same way."

3 They’ve Finally Figured Out Co-Parenting


It didn’t take Reese and Ryan long to figure out their custody arrangement after announcing their separation, as the exes have balanced joint custody of their two kids ever since. Although co-parenting was likely difficult in the beginning, the exes say they’ve reached a point where they’ve got things down pat.

Reese once praised her ex for being such an involved father. “My ex-husband is very involved in raising our beautiful children. We're very lucky because we both grew up in working families,” she explained, Daily Mail reports. “We're on the same page that way.”

She added, “When we're with our children, we're very good about checking ourselves. I'm teaching the children what we were taught growing up - a real set of rules, discipline and love.”

2 Reese Said The Divorce Hurt Her Work

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Although we’d say Reese’s work is on fire nowadays, the actress has admitted that she went through a slump following her divorce, which she blames on how difficult the separation was.

"That was a tough year that followed," Reese said on 60 Minutes in 2014. "I spent a few years just trying to feel better. You can't really be very creative when you feel like your brain is scrambled eggs."

"I was floundering [...] because I wasn't making things I was passionate about, I was just kind of working," Reese continued. "And it was really clear that audiences weren't responding to anything that I was putting out there."

1 They Both Have Kids With Other People Now


Since their divorce over a decade ago, Reese and Ryan have gone on to have children with other people. As we’ve mentioned, Reese and her current husband Jim Toth welcomed son Tennessee in 2012.

Although Ryan has never remarried, he does have a third child. Shortly after ending his relationship with Abbie Cornish in 2010, the actor entered into a fling with actress Alexis Knapp the same year.

Alexis discovered she was pregnant only after they called their relationship off. She gave birth to their daughter, Kai, in 2011, and Ryan was present.

Sources: TMZ, Babble, Us Weekly, Entertainment Tonight, Instyle Magazine, People, Daily Mail, Fame 10

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