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Chris Evans has reportedly dated a slew of Hollywood women, including Lily Collins, Minka Kelly, and most recently Jenny Slate. But his longest relationship was from 2001 to 2006, when a then-baby-faced, not-quite-famous Chris was in an on-off relationship with Jessica Biel, herself a youthful star struggling to build a movie career post 7th Heaven.
Because they were a relatively low-key couple that pre-existed 24/7 blogs, there's not a ton of confirmed information about them on the internet. But admit it: Despite more than a decade passing since their split, you wish you knew more about them. Perhaps your interest was most recently piqued when Chris told Esquire that he and Jessica went skydiving together for Valentine's Day one year. What else did they do together? Why are they such a mystery? For the curious, here's a comprehensive look back at their (frustratingly) not-very-well documented relationship, including photos of Chris with spiky hair.
Unconfirmed Month, 2001: Chris Evans and Jessica Biel reportedly start dating.
December, 2001: Chris stars in Not Another Teen Movie, where he plays a hot jock. He worked out with a trainer to get buff for the film, and not surprisingly, Jessica was a fan. “He was pretty good before … but damn. He really got buff,” she said in an interview with Extra.
Side-note: Long after they split, Chris told Playboy that he likes “a good ass,” which could explain his firm grasp on Jessica’s lower back at a Playstation 2 party in 2001.
December, 2001: The couple is lovey-dovey as they walk the red carpet at the second annual My VH1 Music Awards. Chris debuts a spiky haircut.
March, 2003: They attend the OA Benefit for the War Victims of Sierra Leone in Los Angeles.
August, 2003: They swing by a cocktail reception hosted by LG Mobile Phones.
October, 2003: Here they are at a celebrity gaming tournament for charity, hosted by Mark Wahlberg.
October, 2003: A few days later, they appear smitten at a party for Texas Chainsaw Massacre, which stars Jessica.
September, 2004: The couple star in Cellular, in which Chris plays a college student tasked with rescuing an abducted school teacher (Kim Basinger) and Jessica plays his love interest. In an interview with Boston Magazine, Chris says, “Any time you get to work with someone that you know, it’s gonna lend itself to the on-set relationship. You have to find a certain level of relaxation while you’re trying to perform, and any time you can lean on an existing relationship with someone, it’s only going to help.”
October, 2005: Jessica tells Cosmopolitan the sweet things Chris does for her. “When I turned 21, I actually awoke to find my bed covered in rose petals," she says. "In the middle of the night, he had pulled apart at least 24 roses in all different colors and sprinkled the petals everywhere. He's definitely a keeper." She also reveals that they'd discussed getting married. “We always talk about it," she says. "We both want to be married, and we both want to have children.” And she shares that she liked to cook for him when he was "working hard." "When he comes home, I'll have dinner ready. It's old-fashioned and fun, and I feel kind of homemakery and great doing it.”
February, 2006: Chris and Jessica star in the indie drama London. Chris plays Sid, the drug-addled ex-lover of Jessica's character. The two have some amazing on-screen chemistry, but the couple calls it quits only a few months after the movie premieres. Later, in an interview with W Magazine, Chris reveals that he related to his London character, perhaps a bit too much. “I’ve had those arguments with women; I’ve said those things," he said. “Sadly, I related to that narcissistic drug addict!”
February, 2006: Pre-breakup, Jessica and Chris hit the London red carpet with co-stars Joy Bryant and Dane Cook.
April, 2006: The pair is spotted smooching as they walked Chris's dog, East. This is the last time they are photographed publicly before their split.
June, 2006: News breaks that the couple has called it quits; to this day there are no confirmed reports about why they ended their relationship. Sad but classy.
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