Drew Barrymore Learned an Important Lesson From a Cheating Boyfriend

Drew Barrymore learned an important life lesson from a cheating boyfriend when she was still a Hollywood teenager. Though she confessed she “felt shame” at first and wondered why she wasn’t good enough for that person to remain faithful, she soon came to an important realization. And decades later, she said she hopes she can raise her daughters with knowledge of the lesson she learned.

Drew Barrymore in a yellow top, smiling and leaned on one elbow with the other hand on her hip
Drew Barrymore | Dimitrios Kambouris/Getty Images for Empire State Realty Trust

Drew Barrymore felt ashamed after a boyfriend cheated on her when she was a teenager

Barrymore told Elle magazine when it came time to define beauty for her daughters, Frankie and Olive, she was willing to do whatever she could to teach them “insecurity is not an option.”

She recalled when a boyfriend cheated as a teenager, she tried to figure out where she’d gone wrong. “I remember feeling so bad about myself, and I felt shame,” she explained. “I asked myself why I wasn’t good enough, and I thought the other girl must’ve been so great.”

Fortunately, the child acting icon soon started looking at the situation differently. She asked herself some questions and wondered what if she “decided to never think this way again?”

Drew Barrymore learned a new way to look at herself from her cheating boyfriend

After feeling bad, Barrymore said she wondered, “What if I decided that I’m just what I am and realized that someday I would meet someone and I would be enough for him? What if I didn’t try to warp myself into this phantom standard that I didn’t even know?”

According to the Scream actor, that was a real “script flip” moment moving forward in relationships. “Instead of being insecure and jealous and suspicious and wonder if every guy is going to cheat on me again,” she shared, “I decided to say, ‘Nope. This will be totally enough for somebody one day.'”

In other words, she realized she didn’t deserve to be cheated on. And she learned she shouldn’t have assumed something in her own character caused it to happen. Most importantly, she knew not to carry the insecurities caused by one failed relationship with her into the next.

In the end, she brought the interview with Elle magazine back to Frankie and Olive and said, “So I feel like I want to teach stuff like that to them.”

Drew Barrymore’s taste in partners changed after becoming a parent

Barrymore’s view of herself changed when her boyfriend cheated. And she explained to Jimmy Fallon on The Tonight Show, her taste in romantic partners has matured since she became a parent. She said she started looking for more responsible traits, like evaluating parenting styles and looking for accountability.

She said, “When you’re young, you’re not like, ‘Oh I bet they could really pick that kid up on time from school.”

As a parent, though, she said it’s more important to know a partner will be reliable in that sense. Now a single, talk-show-hosting mom of two, she’s confessed to using dating apps on The Drew Barrymore Show. And she told ET in February 2022, “I think I’m averaging, like, one or two dates a year, which feels constant in a busy life.”

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