Drew Barrymore reveals awkward moment she hit on a stranger in Central Park

The actor told Gayle King about shooting her shot with a stranger during an episode of ‘The Drew Barrymore Show’

If there’s anything to know about Drew Barrymore, it’s that she always keeps her fans guessing. During Monday’s episode of The Drew Barrymore Show, the actress told guest host Gayle King about her exciting weekend before diving into the show’s current events segment.

“I saw this man in this park and he was really cute and I was attracted to him,” she begins her story. “So, I start following him.”

The 50 First Dates star explained to the audience that she was also wearing a balaclava when she approached the stranger, so her entire face was covered and only her eyes peeked through.

“So, I just meandered over to him and I just went, ‘Hi, I was just wondering if I could ask you a question,” Barrymore said. She asked the man if he was single, and he replied, “Perhaps?”

“And I said, ‘Okay, are you gay?’” she told the audience. Gayle King was in shock that she would ask a stranger a question like that, but Barrymore explained that she has no “gay-dar” and always falls for the wrong guy. No, the stranger in the park was not gay, but the Charlie’s Angels star told him that he inspired her to take a risk.

“I said, ‘I just wanted to do something that I could be proud of today by taking a risk, and you compelled me to take that risk,” the talk show host told Gayle King. “And he said, ‘Well I am proud of you.”

At that moment, the single mother removed her balaclava, but not without asking the man’s age: “He said, I’m 28.”

The 46-year-old actress groaned with her head in her hand. “I guess that’s our first strike,” she said. “I’m twice your age, that’s probably not going to work.”

Then, a female fan came up to Drew in the park to let her know that she overheard their conversation. “I just heard you ask this man if you’re single and I think it’s so great,” the fan told her. “And, are you Drew Barrymore?”

While no love connection was made between Barrymore and the man, she left the interaction feeling great and it sure made for a funny story.

The actress has opened up about the struggles of dating as a single mom. In a conversation with Bobby Berk for The Drew Barrymore Show, Barrymore told the Queer Eye star that she doesn’t think she’s fully ready to date, or to introduce a potential partner to her daughters.

“I don’t know how to date with kids,” Barrymore said as she teared up. “I’m not there yet. I have two young girls and, like, I don’t want to bring people home.”

Drew Barrymore shares her daughters Olive, 9, and Frankie, 7, with ex-husband Will Kopelman. The two were married in 2012, but divorced in 2016.