Drew Barrymore's Experience With Online Dating Went Terribly Wrong

No one is safe from experiencing the dread of online dating — not even celebrities. Following Drew Barrymore's divorce from art director Will Kopelman in 2016, the "Charlie's Angels" star decided to re-enter the dating scene. In a 2021 appearance on "CBS Mornings," Barrymore candidly shared the struggles of dating as a single mom, revealing, "I'm not there yet."

A year later, Barrymore appeared on NBC's "The Tonight Show Starring Jimmy Fallon" and discussed her dating preferences. While recounting a Zoom date experience, Barrymore admitted it wasn't terrible but that she "still [wanted] to meet someone the old-fashioned way." Nevertheless, the actor didn't completely dismiss the idea of using dating apps.

Unfortunately, Barrymore did not find what — or who — she was looking for. During an episode of her talk show, "The Drew Barrymore Show," the actor shared a rather relatable dating app horror story. In a clip posted to TikTok, Barrymore detailed, "This guy on my app said he was the quarterback for the Los Angeles Rams." However, after striking up a conversation, the star found out that the man was actually not who he claimed to be.

During the segment, Drew Barrymore recalled how she was excited to talk to a football player who played for a Los Angeles team; at least that was what she thought was happening. "He was not the quarterback for the LA Rams," Barrymore shared, explaining, "He was a musician who thought he was being cute." After the man reached out again, the star told him off. "You made me feel stupid. I don't know who you are," she told him.

Unfortunately, this wasn't Barrymore's only experience with online dating that went terribly wrong. In a 2021 episode of "The Drew Barrymore Show," the host revealed that she even got stood up once. After setting up a date with a man she had matched with on a celebrity dating app, the guy never showed up. "He stood me up at the exact time we were supposed to meet," Barrymore recounted, adding, "I was like, 'Can't you be a jerk like an hour before?' That would have been such a time saver."

Despite the negative experiences, Barrymore admitted that she keeps returning to dating apps for another shot at romance. In 2023, the "50 First Dates" star shared with her talk show audience that she checks her dating app every six months, quipping, "I'm like, 'Well, clearly, this is where everybody is.'" However, she mostly finds herself disappointed with the lack of new faces. Fortunately, her persistence paid off, as the actor eventually met someone on Raya, a members-only dating app.

In a surprising twist, Drew Barrymore casually dropped a bombshell about her love life during a 2023 conversation with Gwyneth Paltrow on "The Drew Barrymore Show." As they discussed Paltrow's marriage, the topic shifted to dating apps, and Paltrow suggested getting Barrymore on one. To everyone's surprise, Barrymore revealed, "Funny enough, the one person I've been sort of seeing in and around for the last three and a half years, I oddly met on Raya."

Paltrow seemed surprised by the revelation, suggesting Barrymore's fling might not have been serious up to that point. However, Barrymore went on to share more significant news, disclosing that she had invited the guy to a wedding with her. Interestingly, it was Taylor Swift and Travis Kelce's relationship that inspired her to do so.

In another episode of her talk show in 2023, Barrymore admitted that it was seeing Swift attend Kelce's Chiefs games that made her realize it was acceptable to publicly date. She shared, "There was something so normal about it. She just went on a date, and it made me think, 'I could just go out on a date.'" While Barrymore previously shared that she won't ever get married again, having some fun on the dating scene is clearly not off the table for the star.