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
chung chi 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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EXCLUSIVE
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.