Why Drew Barrymore And Justin Long's Relationship Was Never Going To Last

After meeting in 2007 while shooting the rom-com "He's Just Not That Into You," Drew Barrymore and Justin Long quickly snagged a spot among one of Hollywood's most endearing couples. But their romance dwindled before the movie came out in 2009. In the summer of 2008, just a few months into their relationship, Barrymore and Long split. Long reportedly took the breakup hard, going so far as to withdraw from her directorial debut "Whip It," E! News reported.

"He couldn't stand working with her and not being with her," a source close to Long said. "He's too upset." The insider also dished on Barrymore's state of mind during that time. "She was hot and cold. One minute she was in love with him and the next she wanted to break up with him." (A rep for Long later clarified that the "Tusk" actor was never formally attached to the project.) The breakup surprised fans all around, as Barrymore and Long appeared smitten with each other up until they split. 

But it wasn't going to be end of the couple. After reuniting for the 2009 "Going the Distance," the exes reignited their romance and attended a series of events together. "I adore him," Barrymore told People at the "Grey Gardens" premiere in April 2009. But by October 2010, the couple went their separate ways — this time for good. Even though Barrymore and Long gave their relationship another chance, both of them knew they weren't meant to together for very long. 

Drew Barrymore and Justin Long, who were in their early 30s and late 20s respectively when they started dating, believe they lacked the maturity to make their relationship work. "We were, you know, more hedonistic, more immature," Barrymore told Long while reminiscing about their relationship in his guest appearance on "The Drew Barrymore Show" in September 2022. That doesn't mean their memories from their time together weren't worth it.

Quite the contrary, actually. "We would get together, we would break up, you know. There was chaos. It was hella fun," she quipped. Long agreed with his ex. "Fun chaos. Well, yeah, most hedonism is fun. There's not a lot of bad hedonism," he concluded, drawing laughter from the host. Their penchant for jokes was one of the reasons they were together at all. "We laughed so much," she said. "Like that was so much a part of our connection was that we love funny people. We enjoy laughing at all times."

Even though their relationship wasn't meant to last, Barrymore and Long remained friends after their split. Because that can be unusual for many, their hanging out sparked romance rumors in 2018. "They are both single and they are spending time together," a source told E! News, before explaining nothing else was going on. "That's all it is for now." And it stayed that way. After divorcing Will Kopelman in 2016, Barrymore has remained single. But Long became engaged to Kate Bosworth.

Drew Barrymore told Justin Long she was elated her ex-boyfriend had found true love in Kate Bosworth. "All I want in life is your success and happiness. I'm just so happy because you deserve to be happy. I'm so thrilled for you," she told him on her talkshow. Long and Bosworth, who have been in a relationship since they met while shooting "House of Darkness" in early 2021, confirmed their engagement in an April 4 Instagram post, after sparking speculation earlier in the year. 

The former child actor wasn't bluffing, either. In May, Barrymore hosted Bosworth herself on "The Drew Barrymore Show" and both actors showed admiration for each other. "That kind of inner glow, that shine that you give so many people," Bosworth said. Barrymore and Bosworth weren't afraid to discuss Long. In fact, the "Blue Crush" actor revealed she encouraged her fiancé to go on the talk show the previous year. "I was with him when he got the ask ... And I said, 'You have to do it,'" Bosworth told Barrymore.

Bosworth knew it was the right thing to do. "He loves you so much," she said. "He just loves you so, so deeply." Bosworth seemingly understands the kind of relationship Barrymore and Long had. "I always say you guys were in the tornado together, right? It's like the time in your life when you're like, 'I want to feel and I want to do everything,'" Bosworth described.