Chris Evans Almost Married Jessica Biel and Other Surprising A-Listers Captain America Has Dated

In recent years, Chris Evans’ career has exploded thanks to his role as Captain America in the Marvel Cinematic Universe. But for two decades, Evans’ private life has been a popular topic with fans because he continues to be one of the most eligible bachelors in Hollywood.

Chris Evans
Chris Evans | Mark Davis/Getty Images

Chris Evans and Jessica Biel almost tied the knot

Evans moved to Los Angeles in 2000 to start his film career when he was 18 years old, and just one year later he landed a role in the parody flick Not Another Teen Movie. At the same time, Evans started dating 7th Heaven star Jessica Biel, and they worked together on two films during their relationship: London and Cellular.

Evans and Biel dated for five years, and she told Cosmopolitan one year before their breakup that they talked about marriage regularly.

“We always talk about [marriage],” explained Biel. “We both want to be married, and we both want to have children.”

Chris Evans Jessica Biel
Chris Evans and Jessica Biel | Jon Kopaloff/FilmMagic

Since her breakup with Evans, Biel has moved on and is now married to Justin Timberlake and they are the parents of two children. Evans, however, hasn’t made it down the aisle yet.

In the years after his split from Biel, Evans briefly dated Friday Night Lights star Minka Kelly, Shameless star Emmy Rossum, and Glee star Dianna Agron. Evans was also briefly linked to Sandra Bullock after her divorce in 2010.

It wasn’t until 2016 that Evans would find himself in another serious, long-term relationship.

Trying to make it work – twice

Evans fell for his Gifted co-star Jenny Slate in 2016, but the couple amicably split in February 2017 due to conflicting schedules. One month later, the Saturday Night Live alum gushed to Vulture about everything she loved about Evans.

“He’s really vulnerable, and he’s really straightforward,” said Slate. “He’s like primary colors. He has beautiful, big, strong emotions, and he’s really sure of them. It’s just wonderful to be around. His heart is probably golden-colored, if you could paint it.”

Chris Evans Jenny Slate
Jenny Slate and Chris Evans | Emma McIntyre/Getty Images

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Evans and Slate gave their romance a second try later that year, but by March 2018 they were done for good. After the second breakup with Slate, Evans admitted that he “definitely” wanted to be a dad and have a family, but he didn’t want to “put the cart before the horse.”

He explained that a family only works if it’s built off the extension of the love one person feels for another. If, all of a sudden, someone wants a child more than the relationship, then they “may be on shaky ground.”

Chris Evans is dating different women and ‘having fun’

In between his two major relationships, Evans has had the opportunity to date plenty of different women over the years. He attended the 2007 Met Gala with Christina Ricci, cameras spotted him leaving a London club in 2010 with Butterfly Effect star Amy Smart, and he was reportedly “all over” Twilight actress Ashley Greene at a club in 2011.

In 2015, the Avengers: Endgame star was linked to Lily Collins after they met at the Vanity Fair Oscars party. And, rumors also swirled for a while that Evans hooked up with his Avengers co-star Elizabeth Olsen. The duo denied those rumors, laughing them off and making it clear they were just friends during an interview with Ellen DeGeneres.

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Most recently, Evans has been linked to Mamma Mia! Here We Go Again actress Lily James after they were spotted together in London in July 2020. Neither Evans nor James have confirmed they are dating, but the photos show that the duo looked happy together while eating ice cream and laughing in the park.

An insider recently told Us Weekly, that the Knives Out star has been “dating different women and having fun.” However, moving forward, Evans wants to be “more private with his love life.”