The Truth About Chris Evans And Jessica Biel's Relationship

The early '00s may seem like forever ago, but the questionable fashion choices of the era have made somewhat of a comeback in 2022. Thanks to stars like Olivia Rodrigo and Dua Lipa, Y2K fashion is back in style. Not only that, but Ben Affleck and Jennifer Lopez are back together. Arguably one of the biggest couples of the time, the stars are giving millennials one hell of a nostalgia trip with their recent engagement announcement.

Out of all the couples dominating the headlines at the time -– think Britney Spears and Justin Timberlake, Jessica Simpson and Nick Lachey –- one couple that fell under the radar was the relationship between Chris Evans and Jessica Biel. While the pair were starting to become known thanks to Biel's role in "7th Heaven" and Evans' appearance as a jock in "Not Another Teen Movie," they were relatively unknown in the pantheon of Hollywood couples.

According to Us Weekly, the pair began dating in 2001 but seeing as Biel has been happily married to Justin Timberlake since 2012, her relationship with Evans obviously didn't pan out. So what exactly happened between the two that made them call it quits?

As InStyle notes, around the time Chris Evans and Jessica Biel started dating, the actress was in her 6th season of "7th Heaven" while Evans had just finished filming "Not Another Teen Movie". Biel was quite a big fan of the movie, especially when it came to Evans' character. "He was pretty good before ... but damn. He got really buff," she said during an interview with Extra, per Cosmopolitan.

Evans and Biel would go red carpet official in December 2001, appearing at the last My VH1 Music Awards. The couple shared a decent amount of PDA at the event, per AmoMama, and continued to make appearances on red carpets and other press events during their five-year romance. Their public appearances contrasted how little they actually spoke of their relationship in the first years they were together. But towards their penultimate breakup, Evans and Biel became more open about their connection –- especially when rumors of an engagement began to circulate.

In 2004, Chris Evans and Jessica Biel had just starred in their first film together called "Cellular." Also starring Kim Basinger and Jason Statham, the movie sees Evans play a college student who has to rescue a teacher who's been abducted. Biel plays Evans' love interest in the film, something that the actor would explain as being a relaxing experience. "Any time you get to work with someone that you know, it's gonna lend itself to the on-set relationship," he told Boston Magazine. "You have to find a certain level of relaxation when you're trying to perform, and any time you can lean on an existing relationship with someone, it's only going to help."

Rumors of their engagement started circulating around this time, resulting in Biel addressing the gossip during an interview with Cosmopolitan in 2005. When asked whether they've talked about getting married, Biel said they "always talked about it" and shared they "both want to have children." But, as the actress continued, "we're not engaged. So the rumors are false ... so far."

It was during this interview that the actress also revealed the things Evans had done as her boyfriend, including a romantic birthday present. "When I turned 21, I actually awoke to find my bed covered in rose petals," Biel revealed. "In the middle of the night, he had pulled apart at least 24 roses in all different colors and sprinkled the petals everywhere."

Chris Evans and Jessica Biel starred in their second and final film together in 2006. The movie, titled "London," saw Evans play Syd, a drug addict hellbent on getting his ex-girlfriend London back, played by Biel. During an interview with W Magazine, Evans said he may have gone a bit too far with inhabiting the character. "I've had those arguments with women; I've said those things," he said. "Sadly, I related to that narcissistic drug addict!"

Whether those arguments bled into Evans and Biel's life as a couple is anyone's guess, but they did break up shortly that same year, per Us Weekly. Neither have spoken about why they decided to part ways, but Evans has said he's never experienced a bad breakup. When asked by Elle how he deals with bumping into exes, Evans said that while "it's very rare" he typically gives them "a big hug, and it's wonderful to catch up."

"If you're ever fortunate enough to love someone and have them love you back, it's worth protecting that," he continued. "It's rare that someone can truly know you. And if you've broken through that kind of wall, I think it's important to value that."

A year after Chris Evans and Jessica Biel broke up, the actress started dating Justin Timberlake, per TheThings. The two had met during a party he was hosting, and he asked a friend if he could ask her out. "There was nothing starry about the way we got together," the popstar told Us Weekly. "It was very un-Hollywood-esce, in fact. We met and got talking. Afterwards I asked my friend if I could call her and ask her out. My friend called Jessica and Jessica said yes, so I called her."

After four years as a couple, Biel and Timberlake broke up for a short spell in 2011. The actress reportedly dated Gerard Butler during this period, but she was soon back together with Timberlake. A year after the breakup, they were married, per People. "She is the single-handedly most significant person in my life," Timberlake told Vanity Fair after they got back together. "In my 30 years, she is the most special person, O.K.? I don't want to say much more, because I have to protect things that are dear to me –- for instance, her."

By 2015, Biel and Timberlake welcomed their first son Silas to the world, per The Blast. In 2020, they revealed they'd had another son named Phineas, per Brides.

As for Chris Evans, the actor has been linked to numerous women since breaking up with Biel. According to POPSUGAR, he's either dated or been romantically linked to the likes of Kate Bosworth, Christina Ricci, Amy Smart, Dianna Agron, Ashley Green, Sandra Bullock, and Lily Collins. Evans was in a pretty serious relationship with Jenny Slate for some time, after the two starred opposite each other in the movie "Gifted." But in the end, the two were "really, really different" and it didn't work out, as Slate told Vulture.

Speaking of their breakup, Slate said that while they're "not on bad terms" they haven't really spoken to each other since things ended. "I think it's probably for the best. I'd love to be his friend one day, but we threw down pretty hard," she said. "No regrets, though. Ever." Evans had similar feelings. "You know, relationships are tricky, there are a lot of moving pieces," he told USA Today. "But I am endlessly grateful for having met her. She will be in my life always."

Most recently, Evans has been linked to British actress Lily James. While neither have confirmed or denied the relationship, they were spotted in London during the summer of 2020, per The Sun.