Drew Barrymore and Justin Long go way back. And we mean way back. As you may recall, these two were actually dating at the time, but went their separate ways in 2008 after about a year of dating, per People. Things heated up pretty hot in that relatively short time, however, as the two were spotted across the country celebrating Thanksgiving in Long’s hometown and Barrymore’s close friend Cameron Diaz’s birthday in Las Vegas. They then reunited for a short time, but split again in 2010.
However, they clearly remained friends after all that on/off romance. In 2020, Barrymore couldn’t help but gush about her ex in the comments section of a now-deleted “Justin Long appreciation post” on Instagram, with comments from celebs reporting that she wrote, “[You’re] not wrong. He’s awesome!” Long then partially replied, per Entertainment Tonight, “I’m texting you with a great photo booth pic I just found clean during my quarantine!” Adorable!
But that was not all. Barrymore then attacked her former boyfriend again, saying on A Little Bit Extra in July: “You want to know why he gets all the ladies? Well, there are a few reasons, but the comedy definitely is [one of them]. He’s one of the hottest, funniest [people], he’s brilliant and he’ll knock your socks off with a laugh. We were together for many years, I was very much in love with Justin. You know why? Because he’s funny.” But that certainly wasn’t the last crush.
Drew Barrymore cried while interviewing Justin Long
Drew Barrymore once again proved how much she appreciates her ex-boyfriend Justin Long, this time crying as they reunited for the September 12 episode of The Drew Barrymore Show. An Instagram clip showed Barrymore clenching while hugging the ‘Dodgeball’ star and telling him, ‘I feel like we’ve been through so much together, so high Justin.’ I always wanted to show you what a different person I was back when we met.” Long then replied, “You were the best,” before Barrymore added, “We had so much fun, but we were more hedonistic. A little bit immature. We’d meet, we’d break up. It was chaos, it was fun as hell.” To prove he really is one of the funniest guys, Long then quipped, “Fun Chaos, well, yeah, most hedonism is fun.”
These two have certainly come a long way, but it seems there isn’t much romance left here. Per People, Long loved Kate Bosworth, but that didn’t stop rumors that he and Barrymore reconciled when they were both single. E! News claimed back in 2018 that the former couple was spending more time together, and had a source calling a “very special connection and bond” that never went away. However, it looks like that’s all platonic now, which puts these two in the running to be our favorite friendly ex-boyfriends.