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.