Ryan Reynolds Dating History: How Many Actresses Did Ryan Reynolds Date Before Marrying Blake Lively?


Ryan Reynolds is a Canadian actor, film producer, and screenwriter. He is now best known as the face of Deadpool, the Marvel superhero with a sense of humor.

However, before Deadpool, Reynolds starred in several blockbuster films, including the likes of ‘The Change Up’, ‘Definitely, Maybe’, ‘Green Lantern’, and ‘The Proposal’.

It’s difficult to think about one of our favorite couples’ past relationships when their current is so exciting. Ryan Reynolds of ‘Deadpool’ fame and Blake Lively, one of Hollywood’s most beloved actresses, always express love and positivity. The couple also maintains a fun atmosphere with each other that fans enjoy.

Reynolds and Lively have their own dating histories, and it’s difficult to imagine how they were before their wedding. Reynolds and Lively actually went on a double date with their respective partners. Let’s see who the ‘Green Lantern’ actor dated before marrying the ‘Gossip Girl’ actress.

1. Traylor Howard 

Traylor Howard and Ryan Reynolds starred in the ABC sitcom ‘Two Guys, a Girl, and a Pizza Place’ in 1998, following their relationship with Melissa. They dated for eight months before splitting up. The 56-year-old actress is now married to business owner and musician Jarel Portman.

2. Melissa Joan Hart 

Reynolds and Melissa Joan Hart appeared in the film ‘Sabrina the Teenage Witch’ together. Ryan was 17 and Melissa was 19 when they had a heated make-out session following a Chelsea Handler interview.

Ryan Reynolds Dating History How Many Actresses Did Ryan Reynolds Date Before Marrying Blake Lively

He won her over by gifting her with a high-end Beluga watch and his charms. Melissa revealed in her 2016 memoir, ‘Melissa Explains It All: Tales From My Abnormally Normal Life,’ that Ryan’s wife Blake Lively is aware of their on-set fling and has even asked Melissa to “help her with a birthday present for Ryan.”

3. Kristen Johnston

Kristen Johnston and Ryan Reynolds had a five-month relationship. The actress is ten years his senior, and she discussed her relationship with Reynolds in an interview with ‘Watch What Happens Live host Andy Cohen.

Reynolds was described by Johnston as a “nice person,” and the two attended the premiere of Tom Hanks’ drama “The Green Mile” together.

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4. Rachel Leigh Cook

Rachel Leigh Cook was in her prime in 2001, with back-to-back songs like ‘Josie and The Pussycats’ and ‘She’s All That’. Ryan Reynolds traveled across the country to London and impressed the ‘Babysitters Club’ starlet. They both had a year of romance before parting ways.

5. Alanis Morissette 

Ryan Reynolds’ marriage to fellow Canadian Alanis Morissette is one of the longest in his dating history. He proposed to her in 2004, and they called it quits after three years. Alanis’ song ‘Torch’ was dedicated to Ryan.

Ryan Reynolds Dating History How Many Actresses Did Ryan Reynolds Date Before Marrying Blake Lively

6. Scarlett Johansson 

Scarlett Johansson, the ‘Black Widow actress, was married to Ryan Reynolds from 2008 to 2011. Scarlett married Reynolds quickly and privately following her divorce from Josh Hartnett in 2008.

Their public appearances as a couple were limited, and they made little to no statements about each other in any personal interviews. ‘The Avengers’ actress revealed in an interview with Vanity Fair that she “glamorized” marriage and “didn’t really have an understanding of it.”

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7. Sandra Bullock 

Sandra Bullock, who co-starred in ‘The Proposal with Ryan Reynolds, began dating him in 2011. The ‘Miss Congeniality actress, on the other hand, denies dating Reynolds. In an interview, she revealed that she had had a “great friendship” with Ryan for ten years.

Ryan Reynolds Dating History How Many Actresses Did Ryan Reynolds Date Before Marrying Blake Lively

8. Agnes Fischer 

When the German model Agnes Fischer and Ryan Reynolds were spotted together in Africa, dating rumors began. Despite this, the two never confirmed their relationship.

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9. Charlize Theron 

Charlize Theron was keen to ‘settle’ and be more ‘serious’, whilst Ryan Reynolds was looking for something more ‘casual’. Reynolds and Theron met through casual friends before starting a family with Blake Lively, and they dated for two months.

10. Blake Lively 

Ryan Reynolds Dating History: How Many Actresses Did Ryan Reynolds Date Before Marrying Blake Lively?

Reynolds met Blake Lively on the set of ‘Green Lantern,‘ in a similar method to how co-stars meet. On September 12, 2012, the ultimate power couple of Hollywood married secretly at the Boone Hall Plantation in South Carolina.

When questioned about the secret of her happy marriage, Lively stated that Ryan is still her ‘best, best buddy!’. The beloved couple is now the proud parents of three children.

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How Many Years Between Ryan Reynolds and His Wife?

11 years for Blake Lively and Ryan Reynolds.

How Did Blake Lively and Ryan Reynolds Fall in Love?

Blake Lively and Ryan Reynolds met for the first time in 2010 on the set of Green Lantern, although they were both seeing other people at the time. By the fall of 2011, both actors were unmarried and they began dating. The couple married in secret on September 9, 2012.

Ryan Reynolds and Blake Lively Were How Old When They Were Together?

Reynolds, now 46, and Lively, 35, first became together in 2011.

Ryan Reynolds Dated Sandra Bullock?

Sandra Bullock and Ryan Reynolds played romantic interests in the 2009 film The Proposal. Rumor has it that the couple didn’t start dating until two years later, in 2011, after Reynolds’ divorce from Scarlett Johansson and Bullock’s divorce from Jesse James.

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