Drew Barrymore Recalls The Night She “Fell In Love” With Justin Long On ‘The Drew Barrymore Show’: “I Was On Tequila … So You Know Where That Leads”

Drew Barrymore reunited with her Charlie’s Angels co-star and longtime friend Sam Rockwell on this morning’s episode of The Drew Barrymore Show, where they recalled the night she “fell in love” with actor Justin Long.

During the nostalgia-filled episode, the two stars reminisced about their time clubbing in Montreal, auditioning for Charlie’s Angels, filming Confessions of a Dangerous Mind and visiting the Playboy Mansion.

According to Rockwell, they even made up names for themselves to go into the Playboy Mansion. While Barrymore went by Daisy Duke and the Oscar-winning actor called himself Demetrius Fontaine, Long opted for a more playful name like Chuckles McGee, which Barrymore said was “not a sexy name at all.”

“But it won your heart,” Rockwell reminded her.

The talk show host then remembered the night she and Long struck up their romance, which lasted from 2007 to 2010 — and how Rockwell played a part.

“I was dating this guy who was the classic he’s just not that into you guy,” she recalled. “Everything I did — I was all in and he wasn’t. So Sam was like, ‘Listen, we’re taking you for drinks.’ And I was like, ‘Thank you!'”

She continued, “I show up in my leather gloves. I got all dressed up because I wanted to feel good about myself. I showed up for drinks with you and Justin. And that’s the night I fell in love with Justin.”

Elsewhere in the interview, Rockwell opened up about meeting his wife Leslie Bibb — and how they ended their first date with margaritas and salsa.

“I was on tequila the night with Justin, so we know where that leads,” Barrymore joked.

The actress then praised her ex-boyfriend as “the best,” adding that he and his current wife Kate Bosworth are “so good for each other.”

In fact, both actors have appeared on The Drew Barrymore Show. During the talk show’s Season 3 premiere in September 2022, Barrymore broke out into tears when she reunited with Long, telling him, “I feel like we’ve been through so much together … We had so much fun but we were more hedonistic. A little more immature. We would get together, we would break up. It was chaos. It was hella fun.”

When Bosworth joined Barrymore for her Season 3 finale in May 2023, she revealed that she was the one who convinced her husband to appear on The Drew Barrymore Show.

“I was with him when he got the ask, and he was like, ‘Oh, Drew wants me to go on her show,’ and I said, ‘You have to do it!’ I was like, ‘Yes, yes you have to do it,’” Bosworth said. “I was so excited because I knew there’s so much love between the two of you.”

The Drew Barrymore Show airs on weekdays on CBS. You can check the website for local airtimes.