5 Dating Struggles Drew Barrymore Has Faced After Being Single For 6 Years

From dating online to being ghosted — Barrymore navigates the modern dating society as a 48-year-old mother to two.

Drew Barrymore kids and ex-husband Instagram

Drew Barrymore has always been candid with her fans about every aspect of her life, one of which being dating, which she jumped back into last year after spending six years single. 

During an interview with Willie Geist in October 2020, Barrymore revealed that it took her five years to look back on her relationship with ex-husband Will Kopelman with “strength, articulation, perspective and hindsight.” 


“I think I’m equally as scared to find love again as I would be if it never happened,” she said. The two were married for four years and share two daughters — Olivia and Frankie.

In December 2022, she confirmed on her talk show that she was dating again.

5 Dating Struggles Drew Barrymore Has Faced After Being Single For 6 Years

1. Being ghosted

During a January 2023 episode of 'On Purpose with Jay Shetty', Barrymore opened up about a recent dating experience where non-mutual feelings left her confused.


She recalled going on the “best date” with a guy in the news industry who she expected to see again. Though she didn’t reveal the mystery man’s identity, she said he seemed like “a responsible human being.”

“We made a plan for that weekend and we were texting back and forth,” Barrymore explained. “And it was so cute. I really liked him. I was like ‘What a nice guy.’”

The sparks fizzled out when she never heard from him again. “I guess that’s what you call getting ghosted,” she said. “I was like, ‘Whoa, that is so… Oh, wow. That’s so weird.’”

She compared this experience to an episode of 'Sex and the City' where Carrie Bradshaw gets broken up with by her boyfriend Jack Berger via a Post-it note that read “I’m sorry. I can’t. Don’t hate me.”


“That is the most giving thing that I could ever ask for in modern society being a single girl,” Barrymore said. “I just wish I could get that Jack Berger Post-it note.”

However, she understands that if the feeling wasn’t mutual, it wasn’t meant to be. She ended her story that didn’t end with a Post-it note on a positive note, saying “You can’t be mad at people because they’re not what we want them to be.”

RELATED: Dark Details About Drew Barrymore's Childhood — And How She Overcame It

2. Accepting love

Barrymore revealed that letting her walls down and accepting love again has been a challenge because she fears she has become “too good at being alone.” Later in Shettys's podcast, her voice broke as she asked “how do you tell people to receive love?”


“I am so stuck and I’m the person who doesn’t want to be stuck,” she tearfully shared. “I want to know what work I could do to take my walls down, believe and trust because I really am trying to figure that out right now.” She went on to say, “I’m still scared or nervous or I don't have any information that shows me that that’s a safe space,” before asking for advice again.

3. Shifting her priorities

Barrymore wrote a candid essay on her personal blog about the difficulty of focusing on romantic love when she feels she already lives “a very rich full life.”

“After two kids and a separation from their father that has made me cautious, I have had the pleasure of shifting my focus when it comes to love for myself and my two daughters,” she wrote. “I know that does not include a man nor has it for a while.”

“It simply hasn’t been my priority,” she explained. “I am someone who is deeply committed to fostering how young girls, my daughters, and myself as a woman, are supposed to function in this world! A relationship with a man has not been top of mind for me for a very long time.”


Barrymore said that just because it isn’t her personal priority to be with a partner, it doesn’t mean it won’t become one someday.

RELATED: Why Modern Dating Has Made Me Stop Believing In Love

4. Having trouble with dating apps

Barrymore claims that although she was glad she got into online dating, the idea of it was better than the real thing.

“I love being able to be in the conversation, I have to say,” she said while discussing dating apps during an episode of ‘Watch What Happens Live With Andy Cohen.'

“I definitely had fun with it. And I’ve always wanted to go on a blind date, but my life got in the way of that, so I thought, like, online dating might satiate that desire. And no, it was a real wake-up call. But it was fun, and yes there were lots of exciting people,” she continued.


The biggest challenge she faced with dating apps was not knowing who she was really dealing with, revealing that she had been stood up and lied to. 

“I got stood up, and I didn’t match with anyone. And my friends gave me this sort of bloated sense of false confidence. They were like, ‘You should try it. You will do great.’ It was a car wreck,” she said.

5. Having young daughters

Another challenge she faces is finding someone she trusts enough to introduce to her daughters.


“I have two young girls, and I don’t want to bring people home,” she said on her show in January 2022. “I think that it would take me a very long time to meet someone and to know them before I could ever even introduce them to my daughters.”

Barrymore has said that Alexandra Micheler — the woman Kopelman went on to marry — is “the most extraordinary stepmom,” to her children. Yet she doesn’t know if she will ever remarry.

“Never. Never, never, never. I will never get married again!” she vowed in an interview with People in 2020

“It doesn’t mean that maybe I wouldn’t like to meet someone, especially when my kids go off to college,” she said. “Or a year from now, I could be totally in love. I’m open to it; I’m not seeking. My cup runneth over. I have so much love in my life.”


RELATED: Drew Barrymore Explains Why She Refuses To Buy Christmas Gifts For Her Kids

Maddie Haley is a writer for YourTango's news and entertainment team. She covers pop culture and celebrity news.