A Look Back At Reese Witherspoon s Relationship History

Less than a year after finalizing her divorce from second husband Jim Toth, Reese Witherspoon has sparked new romance rumors. 

The Legally Blonde star, 48, was recently spotted enjoying the company of financier Oliver Haarmann, 56, in New York City. 

DailyMail.com can exclusively reveal the two have been out on a string of dates, after they were seen together multiple times this week, fueling speculation about a new relationship.

And while she seems to be moving on to a new chapter of her love life, the actress has dated a number of A-listers in the past.

From her marriages to Ryan Phillippe and Jim Toth, to her well-documented relationship with Jake Gyllenhaal, DailyMail.com takes a look back at her high-profile romances. 




While she seems to be moving on to a new chapter of her love life, Reese Witherspoon, 48, has dated a number of A-listers in the past; seen with first husband Ryan Phillippe in 1998





The star most recently sparked romance rumors with financier Oliver Haarmann, 56, after they were seen on a string of dates; they are pictured on Monday




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Reese Witherspoon pictured with the new man in her life a year after SECOND divorce


Jeremy Sisto (1992)

Prior to meeting her first husband Ryan, Reese had already captured hearts off-screen.

The actress dated Jeremy Sisto, 49, best known for his role in Clueless, after the duo met while working on a 1992 TV movie.

Sisto later revealed in a Reddit AMA that Witherspoon was his 'first actress girlfriend.'

'We had a long-distance relationship for a long time. I was so into her,' the actor said.

It's unknown exactly when the pair split up. 




The actress dated Jeremy Sisto, 49, best known for his role in Clueless, after the duo met while working on a 1992 TV movie; Sisto seen in 2003

Ryan Phillippe ( 1997 - 2008)

Their meeting was the stuff of romantic comedies: Phillippe, 49, and Witherspoon crossed paths at her 21st birthday party in 1997 and began dating. 

In a 1998 interview with Jane magazine, the star revealed, 'I don't know what came over me — maybe the seven Midori sours — but I told him, "I think you're my birthday present.

'He thought it was so flattering and now that I think about it … how embarrassing!'

The romance progressed quickly, and in 1998, about a year after meeting, the pair got engaged. 

The couple went on to star in the iconic 1999 romance/thriller Cruel Intentions together, catapulting their stardom. 




Phillippe, 49, and Witherspoon crossed paths at her 21st birthday party in 1997 and began dating. The romance progressed quickly, and in 1998, the pair got engaged; seen in 1998 





The couple went on to star in the iconic 1999 romance/thriller Cruel Intentions together, catapulting their stardom; seen in 2002







Only a few weeks after the movie came out, Reese and Ryan got married in June 1999. 

They said 'I do' in Charleston, South Carolina at the Old Wide Awake Plantation along the Stono River.

The Big Little Lies star was several months pregnant with their daughter, Ava, at the time. 

Reese was 23 when she welcomed Ava — now 24 — in September 1999, three months after their wedding. 

In 2002, Ryan revealed that the pair were attending couples therapy in an interview with New York's Daily News.

'The biggest mistake is not doing that, ignoring it and having the marriage fall apart because of laziness,' he said. 

Their son Deacon — now 20 — was born four years after their daughter. 

Eventually, the fairytale romance began to turn sour. In 2006, three years after having their son, the duo announced they were splitting. 




They got married in June 1999, but eventually the fairytale romance began to turn sour, and in 2006 the duo announced they were splitting; seen in 2002









They share daughter Ava, 24, and son, Deacon, 20; Reese seen with their kids in 2019







They shared a joint statement at the time. 

'We are saddened to announce that Reese and Ryan have decided to formally separate,' a representative for the couple said. 

'They remain committed to their family and we ask that you please respect their privacy and the safety of their children at this time.'

They finalized their divorce in 2008. 

Jake Gyllenhaal (2006 -2009) 

Witherspoon began dating Brokeback Mountain star Jake, 43, in 2006 while working together on the movie Rendition.

The two split in 2009.

At the time a source told Us Weekly that it was an amicable split. 'No one cheated. There was no drama.'

Other sources close to the couple said the relationship had just run its course.




Witherspoon began dating Brokeback Mountain star Jake Gyllenhaal, 43, in 2006 while working together on the movie Rendition; seen in 2007





The two split in 2009. At the time a source told Us Weekly that it was an amicable split. 'No one cheated. There was no drama'; Pictured in Los Angeles in 2009

A friend told U.S. TV network E!: 'They needed time to figure it out and they were on different coasts. When they were finally together, they talked it out and decided they're not going to be together any more.

'There are no other people involved. The relationship just ended. It just fizzled. But they also wanted to be careful and private about it because of Reese's kids.'

Jim Toth (2010 - 2023) 

One year after her split from Gyllenhaal, Witherspoon began dating Hollywood talent agent Jim, 54.

The duo wed in March 2011 and welcomed their son Tennessee — now 11 — one year later. 

In a 2011 interview with Marie Claire, Witherspoon called herself 'very lucky' to have found Toth.

'Now I feel a great sense of relief and an incredible amount of support from my husband... Somebody close to me once said, "Oh, no man will ever accept your children." And I just thought it was the most horrifying thing someone has ever said to me in my entire life.'

'I was determined to find somebody who would make that not true. And I got lucky. I did. I got very lucky, and he's wonderful. And so wonderful with the children. I'm very blessed.'

But after 12-years of marriage, Witherspoon and Toth announced their split in March of 2023.




One year after her split from Gyllenhaal, Witherspoon began dating Hollywood talent agent Jim, 54. The duo wed in March 2011; seen in 2017





They welcomed their son Tennessee — now 11 — one year later; The former pair pictured with Tennessee (middle) and Reese's older kids







'We have some personal news to share ... It is with a great deal of care and consideration that we have made the difficult decision to divorce,' they shared in a statement.

'We have enjoyed so many wonderful years together and are moving forward with deep love, kindness and mutual respect for everything we have created together.

'Our biggest priority is our son and our entire family as we navigate this next chapter.

'These matters are never easy and are extremely personal. We truly appreciate everyone's respect for our family's privacy at this time.'

A week after the announcement, Reese officially filed for divorce.

She cited irreconcilable differences as the reason behind their split in court documents obtained by TMZ. The documents were filed in Nashville, Tennessee, where they live with their son.

The documents reveal the couple agreed to a prenuptial agreement in March 2011. Reese indicated the contract was valid, 'providing "adequate and chung chi (full report) sufficient provisions" for their assets and debts.'

An insider told People that it was 'very difficult' for the movie star to accept that she and her former partner were 'two very different people.'




But after 12-years of marriage, Witherspoon and Toth announced their split in March of 2023; seen in 2020







Someone close to the two noted that the ambitious producer 'has her hand in a lot of pots' and Toth 'prefers less frenzy.'

It was added that, 'They've been spending less and less time together while she was working.'

More than ten years after tying the knot, the longtime duo recently 'found themselves with fewer interests in common.'

Reese is described by a source as 'headstrong and focused' and Jim is said to be 'more laid-back.'

Despite going through a divorce a source close to The Last Thing He Told Me producer told People in April that she has 'no regrets' about ending the union and is 'doing much better now.' 

Oliver Haarmann (2024) 

Reese has been spotted enjoying a number of dates with Haarman - whose ex-wife - businesswoman Mala Gaonkar, 54, is now in a relationship with musician David Byrne, 72.

In snaps from this week she looked chic in a black dress and heels as she hopped into an SUV before a dinner date with Haarmann - who wore a white shirt and blue trousers.

They were also seen on Sunday arriving at a heliport together before heading to an apartment building.




Haarmann was previously married to businesswoman Mala Gaonkar, 54 and the pair have two sons (pictured 2016)

It is unclear how serious their relationship is. DailyMail.com has contacted Reese's representative for comment.

Haarmann - who is German - is a founding partner of Searchlight Capital Partners, a private equity investment firm.

He was previously a senior partner of the global investment firm KKR & Co. He shares two sons with Gaonkar.

He earned a bachelor's degree in history and international relations from NYC's Brown University in 1990, and an MBA from Harvard Business School in 1996.


Reese WitherspoonJake Gyllenhaal