“You want to know why he gets all the ladies? Well, there’s a few reasons, but the comedy is definitely [one of them],” Drew Barrymore said of Long during a May 2022 appearance on the “A Little Bit Extra” podcast. “He is one of the sharpest, wittiest [people], he’s brilliant and he’ll just knock your socks off with laughter.”
The Fever Pitch actress was romantically involved with the Barbarian star on and off from 2007 to 2010, and more than a decade later, she is still one of his biggest fans.
“We dated for many years, I was very much in love with Justin, you know why? Because he’s funny,” Barrymore confessed.
Four months later, the exes reconnected on The Drew Barrymore Show and gushed over each other.
“Now I feel like I have to be funny to live up to the hype,” Long joked in September 2022 about Barrymore’s kind words. “It was so flattering. You’re the funny one. You are one of the funniest people I’ve ever met. We had a lot of laughs. We laughed all the time.”
The Christmas With the Campbells actor — who worked with Barrymore in He’s Just Not That Into You — continued: “I love that we’ve maintained our love. I know from my end it’ll never go anywhere. I will love you always. I mean that.”
Barrymore agreed through tears, saying, “I will always love you so much. You are so important to me. I feel like we’ve been through so much together too. I always wanted to prove to you that I was a different person from when we dated.”
Their relationship isn’t the only one of Long’s romances that started at work. He connected with Bosworth in spring 2021 while filming a horror project, House of Darkness, before they sparked their offscreen relationship.
Us Weekly confirmed in January 2022 that the twosome had been seeing each other since late 2021.
“[They’re] not hiding the fact that they’re together,” a source exclusively told Us at the time, noting that the 21 star and the F Is for Family alum were “just staying low-key and private about their relationship.”
Three months later, Long gave fans a glimpse into his life with Bosworth. “It’s weird. I want to [talk about it], but I also want to be protective,” the Lady of the Manor actor said during an April 2022 appearance on the “Viall Files” podcast. “I want to scream it from the rooftops, but I also want to be protective. It’s sacred.”
The following year, the couple confirmed in April 2023 that they are engaged after the Win a Date With Tad Hamilton! actress was seen wearing a diamond sparkler that March. The magical moment came after the duo attended a joint therapy session.
“I remember waking up not so many mornings after that therapy session and I looked at Justin and I said … I smiled at you, and I said, ‘What do you need?’ And he, like, really looked at me and he said, ‘To spend my life with you,’” Bosworth recalled during an appearance on Long’s “Life Is Short With Justin Long” podcast. “And I smiled and I said, ‘Well, yeah, you have that. Oh my gosh, you have that,’ and he said, ‘No, I mean I really want to spend my life with you.’”
Scroll down to see Long’s most high-profile relationships through the years: