Who: Actor Chris Evans, aka Captain America, 40, and actress, comedian, and writer Jenny Slate, 40.
How They Met: Coincidentally, Evans and Slate are both from Massachusetts and grew up only half an hour away from each other, but their paths never crossed until September 2015 when they met at a "chemistry test" for the film Gifted. Spoiler alert: they passed and were cast as romantic leads.
As for how Slate felt about their initial meeting, she told Vulture, "I remember him saying to me, 'You're going to be one of my closest friends.' I was just like, 'Man, I fucking hope this isn't a lie because I'm going to be devastated if this guy isn't my friend.'" She and Evans did become friends and would regularly hang out at weekly game nights during the duration of filming. But things eventually turned romantic after Jenny separated from her filmmaker husband Dean Fleischer-Camp, with Chris confessing he had feelings for her.
"To be quite honest, I didn't think I was his type," Jenny explained to Vulture. "Eventually, when it was like, Oh, you have these feelings for me? I was looking around like, Is this a prank? I mean, I understand why I think I'm beautiful, but if you've had a certain lifestyle and I'm a very, very different type of person — I don't want to be an experiment."
While Jenny was apprehensive about taking their friendship to the next level, Chris seemingly knew it was meant to be. "Oddly enough, I've only known Jenny for a few months which is insane to say," Evans revealed during an appearance on the podcast Anna Faris Is Unqualified in 2016. "It doesn't [feel like that] at all. Sometimes you just meet the same animal and that's just [what it's like] with Jenny."
Why We Loved Them: They were a classic case of opposites attract. Jenny was quirky and unapologetically embraced her inner weirdo, while Chris was your stereotypical cool guy — some might even call him a bro. But it worked.
Slate was just as skeptical about their differences as everyone else, once revealing: "I didn't know what to expect when I met Chris… He's a giant man with huge muscles and he's Captain America. How could we ever connect?" She admittedly wrote him off as "a sports guy, the kid who likes P.E." However, once she got to know him, he won her over.
"What's the same about us is not just that we're from Massachusetts, which was such a delight, but Chris is truly one of the kindest people I've ever met, to the point where sometimes I would look at him and it would kind of break my heart," she says. "He's really vulnerable, and he's really straightforward. 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, meanwhile, was taken by Jenny's way with words. "I've never ever, ever met someone in my life who has a mastery of the English language the way she does," he previously told People about Slate. "She'll give you one sentence, and there's no fat to it. You're like, 'You just chose such an unbelievable collection of words that beautifully articulate what you say.'"
He continued, "It's like an art form talking with her because the visuals associated with her expression are just so colorful. She's so vulnerable, so honest, so interested in other people more than herself. She's incredibly compassionate—there's just nothing to not love about her."
When They Peaked: After months of speculation that their friendship turned romantic, Jenny and Chris went public with their relationship while simultaneously making their red carpet debut as a couple at the New York City premiere of The Secret Life of Pets in July 2016. In his typical bro style, Chris wore a baseball hat and a white polo shirt, while Jenny opted for an off-the-shoulder red lace dress with tiny cutouts.
On the red carpet, Slate gushed about Evans supporting her at the event. "I haven't really had a large premiere before, so it's nice to have someone who knows how it goes," she told Entertainment Tonight at the time, noting that she and Chris both grew up in Massachusetts: "It's kind of like I got my dream 7th grade boyfriend."
The Breakup: The first breakup happened after less than a year of dating in February 2017. Jenny spoke about the split in her profile for Vulture, revealing that Chris's fame partially is what led to them ending things. "Chris is a very, very famous person. For him to go to a restaurant is totally different than for me to go. I sit in my window and I say 'Hi' to people on the street. I have more freedom because I'm not Captain America," she said, adding that the attention became too much for her. "This is what I needed to do to feel normal," she explained. "To be alone."
Slate was also dealing with her separation from Fleischer-Camp. "Even though we had an amicable divorce, I think that's still something that you need to mourn. When you get separated from somebody that you actually care about, it is the destruction of a belief system. That is really, really sad," she said. "I just didn't have the tools. And I didn't think very hard about that, to be honest."
To the internet's collective delight, Chris and Jenny decided to give their relationship another try in November 2017, but they officially split up four months later. In a New York Times profile about Evans's Broadway debut, Evans confirmed that the two called it quits, and the actor subtly touched on the topic by explaining how he recently learned to "listen more and speak less" in his relationships with women. "The hardest thing to reconcile is that just because you have good intentions, doesn't mean it's your time to have a voice," he explained.
Where They Are Now: Evans is currently single, and hasn't dated anyone seriously since Slate — though, in July 2020, he was rumored to be dating actress Lily James after the pair were spotted hanging out on two separate occasions. When asked whether or not they were a couple, James slyly replied, "No comment."
In the years following his and Slate's breakup, Evans reprised his role as Captain America three times and also starred in the mystery film Knives Out in 2019. This month, the actor will lend his voice to another superhero, Buzz Lightyear, in the sci-fi animation movie Lightyear, and in July, he will star in the Netflix action thriller, The Gray Man.
Slate began dating her now-husband, art curator Ben Shattuck, shortly after she split with Evans. The couple wed on New Year's Eve 2021 and are parents to a 16-month-old daughter, Ida Lupine.
The breakup with Evans prompted Jenny to double down on her career. Over the past several years, she not only returned to her voiceover work in animation films but also expanded her work to include romantic comedies, such as On the Rocks and I Want You Back.
#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.