Ryan Reynolds’ Dating History before He Married Blake Lively

Ryan Reynolds’s dating history before his wife includes many famous women. However, he is happily married to Blake Lively, and they share three beautiful children, with one more addition to their family on the way.

Ryan Reynolds is a Canadian-American actor, director, producer, and writer, who made his acting debut when he starred in “Fifteen” in 1990. Since his debut, he has starred in over 70 movies and series.

The actor is renowned for his roles in “National Lampoon’s Van Wilder,” “Blade: Trinity,” “X-Men Origins: Wolverine,” “Deadpool,” “R.I.P.D.,” “Red Notice,” “Green Lantern,” “The Hitman’s Bodyguard,” “The Adam Project,” and more.

Since the beginning of his career, Reynolds has attracted attention because of his relationships with well-known Hollywood women. He married for the first time in 2008 and finalized his divorce in 2011.

Months before he filed for divorce, he had met his current wife, Blake Lively, but they had no romantic relationship. The duo did not start dating until October 2011, a few months after he finalized his divorce.

Rumors of a relationship between them began when they reportedly left his apartment together early one morning. By the end of 2011, they were seen holding hands as the actress visited his family during the holidays.

On September 9, 2012, Lively and Reynolds tied the knot in a secret ceremony in South Carolina. The couple welcomed their first daughter, James Reynolds, on December 16, 2014.

Almost two years later, they welcomed their second daughter, Inez Reynolds, on September 28, 2016, and their third daughter, Betty Reynolds, on October 4, 2019.

The couple constantly pokes fun at each other through their social media pages and keeps their children’s lives private. Although, they have made rare public appearances with their daughters.

On September 15, 2022, when Lively attended the “Forbes Women in Power” event, she showed off her baby bump revealing that baby number four was on the way.

Blake Lively at the 10th Annual Forbes Power Women’s Summit on September 15, 2022, in New York | Source: Getty Images

Melissa Joan Hart

While filming the movie version of “Sabrina, the Teenage Witch,” in 1996, Melissa Joan Hart met Reynolds, who co-starred alongside her as a love interest.

When they met, they were teenagers and soon became interested in each other even though Hart had a boyfriend. She later revealed that the actor made her feel special.

However, after a brief and passionate fling, the actress decided to end the relationship as she reportedly said she was madly in love with her boyfriend of six months at the time.

Ryan Reynolds and Melissa Joan Hart at the MTV’s 10th Annual Rock ‘n Jock Baseball Game on September 10, 1999, in Los Angeles | Source: Getty Images

Traylor Howard

In 1998, when Reynolds starred as Michael Eugene Leslie “Berg” Bergen, a good friend to Traylor Howard’s Sharon Carter-Donnelly in “Two Guys, a Girl and a Pizza Place,” they started dating. Their relationship lasted for eight months before they split.

Howard is an Orlando-born actress with a degree in communications and advertising and a minor in English from Florida State University.

She made her acting debut in 1994 and has starred in movies and series such as “Boston Common,” “Me, Myself & Irene,” “Monk,” “Son of the Mask,” “Bram and Alice,” and more.

Ryan Reynolds and Traylor Howard at the premiere of “Beautiful” on September 25, 2000, in Los Angeles | Source: Getty Images

Kristen Johnson

In 1999, after his breakup from Howard, Reynolds dated Kristen Johnson. While there is no information on when they started dating, the couple attended the benefit premiere of “The Green Mile” on December 6, 1999.

Johnson is a two-time Emmy Award-winning Washington-born actress who studied acting at the Atlantic Theater Company Acting School in New York. In addition, she holds a Bachelor of Fine Arts degree in drama from New York University.

She is known for her roles in “3rd Rock from the Sun,” “Ugly Betty,” “The Exes,” “Mom,” “Bride Wars,” “Strangers with Candy,” “Life Happens,” “Vamps,” “Daytime Divas,” “Austin Powers: The Spy Who Shagged Me,” and more.

Kristen Johnson and Ryan Reynolds at the premiere of “The Green Mile” on December 6, 1999, in Los Angeles | Source: Getty Images

Rachel Leigh Cook

Model, actress, producer, and writer, Rachael Leigh Cook met Reynolds in 2001. She had to go to London to film at the time, but the actor traveled the distance to win her over as he wanted a relationship with her.

They immediately started dating, and their relationship lasted for one year before they called it quits. Although, there is very little information on why it didn’t work out between them.

Cook’s professional career began when she was ten and working as a child model. When she turned 14, she started auditioning for movie roles and made her acting debut in 1995, starring as Mary Anne Spier in “The Baby-Sitters Club.”

By 1999, she had cemented her celebrity status after she appeared as Laney Boggs in “She’s All That.” She soon became one of the most sought-after actresses in Hollywood.

The actress has starred in movies and series such as “Love, Guaranteed” “Batman Beyond: Return of the Joker,” “Josie and the Pussycats,” “Perception,” “Blow Dry,” “Texas Rangers,” “Nancy Drew,” “He’s All That,” “Psych,” and more.

Ryan Reynolds and Alanis Morissette at the 2003 MTV Movie Awards on May 31, 2003, in Los Angeles | Source: Getty Images

Alanis Morissette

Reynolds had reportedly met singer, songwriter, and actress Alanis Morissette in 2002 when they both attended Drew Barrymore’s birthday party.

They started dating almost immediately and were in a passionate relationship for two years before getting engaged. By June 2006, there were rumors they had split, but they neither confirmed nor denied the rumors.

In February 2007, their representatives said that the couple decided to end their engagement. However, they planned on remaining close friends while having the utmost love and admiration for each other.

Ryan Reynolds and Scarlett Johansson at the 2010 Annual Tony Awards on June 13, 2010, in New York | Source: Getty Images

Scarlett Johansson

In April 2007, Ryan Reynolds started publicly dating actress, producer, and director Scarlett Johansson. Despite their celebrity status, the couple kept their relationship away from the spotlight.

One year later, in May 2008, their representatives confirmed that the couple got engaged. However, other sources revealed that their engagement had happened for a while before it became public.

On September 27, 2008, they married in a private, intimate, and quiet ceremony on Vancouver Island. Although, by early 2010, they reportedly lived apart, leading to rumors of a split.

Reynolds and Johansson debunked the rumors, which continued when they put up their Hollywood home for sale in the Spring of 2010. They bought another house in the Summer of the same year.

Unfortunately, on December 14, 2010, the couple announced their separation after two years of marriage. They stated that they mutually agreed to end their marriage and were doing so with love and kindness.

Years later, Johansson hinted that being married to an actor was challenging, and her relationship with Reynolds may have been competitive because they were in the same industry.

Ryan Reynolds and Sandra Bullock at the premiere of “The Change-Up” on August 1, 2011, in Los Angeles | Source: Getty Images

Sandra Bullock

One month after Reynolds filed for divorce from Johansson, there were rumors that he was dating actress and producer Sandra Bullock.

At the 68th Golden Globe Awards on January 16, 2011, the actress debunked the rumors when the journalist and television personality Al Roker asked about their relationship.

The actress revealed that Reynolds had been a wonderful friend for a decade, and she wished there were more friendships like what they had. She clarified that there was no romance between them as she did not get his loving after dark.

Agnes Fischer at the premiere of “Puncture” premiere on September 15, 2011, in New York | Source: Getty Images

Agnes Fischer

In early March 2011, Reynolds was seen with German model Agnes Fischer during “Safe House” filming in South Africa. The model had reportedly visited him on and off the set, creating rumors that they were dating.

Fischer was known to have done more fitness ads than fashion and was known for the ads she had done for Reebok, Sure deodorant, Bebe, Adidas sportswear, and more. However, the couple never commented on their rumored relationship and was together for a brief period.

Charlize Theron

Shortly after his divorce from his first wife, a mutual friend introduced Reynolds to actress and producer Charlize Theron in the Summer of 2011.

They immediately started dating and kept their relationship out of the spotlight until June 5, 2011, when the paparazzi saw the actor leaving her home. Unfortunately, their relationship lasted for only two months.

According to a source, while the actor wanted a casual relationship, the actress wished for something serious as she hoped to start a family. In addition, their conflicting schedules caused him to end the relationship.

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