Jessica Biel and Then-Boyfriend Chris Evans Did the Most Terrifying Thing on Valentine's Day

#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.

Jessica Biel and Then-Boyfriend Chris Evans Did the Most Terrifying Thing on Valentine's Day
Photo: Getty Images

Who: Emmy and Golden Globe-nominated actress Jessica Biel, 40, and Captain America star Chris Evans, 41.

How They Met: The circumstances of Biel and Evans's introduction are unknown (to methey ~probably~ know how they met), I'd guess they ran in similar young, hot actor circles. The pair began dating in 2001, which, for reference, was the year Evans starred in and was best known for Not Another Teen Movie, and about six seasons into Biel's tenure on 7th Heaven. If the cultural context isn't enough to transport you to the land before smartphones, here's a reminder of what it looked like:

Jessica Biel and Chris Evans My VH-1 Music Awards 2001
SGranitz/Getty Images

Why We Loved Them: From the sounds of it, Jessica and Chris were that super cute, super active (and frankly super annoying) couple who are always trying new things and gushing over their "person" in ultra-curated Instagram posts. Like, they went skydiving — for VALENTINE'S DAY. Nothing says "I love you" like a life-threatening plunge into the cloudy abyss … When they weren't adventuring, the couple was busily co-starring in poorly received films — thriller Cellular in 2004 and romantic drama London the following year.

When They Peaked: In a 2005 interview with Cosmopolitan, Biel opened up about what Evans was like as a boyfriend, revealing that he surprised her on her 21st birthday by scattering rose petals on her bed. Biel made herself sound like a lovely partner as well, explaining that she loved to take photos of Chris and his dog and also enjoyed cooking for him (the human "him"). "It's old-fashioned and fun, and I feel kind of homemaker-y and great doing it," she told the outlet.

Jessica Biel and Chris Evans standing in front of The Texas Chainsaw Massacre promo background
Jon Kopaloff/Getty Images

The Breakup: By 2006, Chrissica (Jiss?) was no longer. Neither actor is particularly fond of discussing their love lives publicly, so we don't have a ton of clues as to what went wrong between the couple. I mean, just one year prior Biel had said that she and Evans "always talk about" marriage — the trail is cold.

Jessica Biel and Chris Evans
Jean-Paul Aussenard/Getty Images

That being said, Evans has alluded to reasons his previous relationships have ended.

In a 2013 interview with W, Evans admitted that he could be argumentative in his past relationships. Speaking of his character from the 2005 film London, in which he starred opposite Biel, the actor admitted he could relate to the "narcissistic drug addict" he played. "I've had those arguments with women; I've said those things," he noted.

In an Esquire profile in 2017, the actor discussed the strain of his field of work on a relationship, explaining, "Letting someone go to work with someone for three months ... they won't see them. It really, it certainly puts the relationship to the test."

Just this year, Evans admitted that retaining his independence is key in a relationship. "I really like to be with someone who also has their own thing to do as well," he told The Hollywood Reporter. "If I'm with someone who just kind of adopts my life, that can feel a bit suffocating."

But reasons for the split aside, Evans claims he's on good terms with all his exes. "I've had no bad breakups in my life," he told Elle. "Typically, if I see an ex, I give 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. 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."

Jessica Biel and Chris Evans at PlayStation 2 and Mark Wahlberg Host Celebrity Gaming Tournament for Charity
Jean-Paul Aussenard/Getty Images

Where They Are Now: Not long after splitting from Evans, Biel took up with a quiet indie singer you've probably never heard of, Justin Timberlake. After breaking up and making up in 2011, the pair wed in 2012. They welcomed their son Silas in 2015 — and in 2020 they welcomed their second son, Phineas.

Biel, who earned raves in the anthology series The Sinner, returned to TV with the supernatural Facebook Watch crime series Limetown and Hulu series Candy.

Post-Biel, Evans dated actresses Minka Kelly and Jenny Slate. He was also briefly linked to Lily Collins and Elizabeth Olsen, though neither of those relationships were confirmed.

Evans went on to star in a quiet indie franchise that you've also probably never heard of … Captain America? The Avengers? Ring any bells? Looking at his movie and TV credits for the past few years, the actor may have just been too busy for a relationship. He appears in the murder mystery Knives Out, the Apple TV+ miniseries Defending Jacob, The Gray Man and was the voice of the voice of Buzz Lightyear in Lightyear.

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