Drew Barrymore is 50 years old. She got divorced for the third and final (?) time about a decade ago. Her third husband was Will Kopelman, the father of her two daughters. Since that divorce, Drew has said that she really doesn’t date that much and she’s not interested in remarrying. Which I respect in general, and I respect specifically for Drew. She was a romantic with a wild streak who settled down with someone who promised a more sedate, traditional life. When it crashed and burned, I felt like Drew was like “okay, maybe I just won’t do any of this sh- again” (but you know, in a more Drew way). Well, on Drew’s talk show, she was asked if she would – at her current age – ever date a 20-something man. Her reaction was funny.
Drew Barrymore can’t see herself paired up with a younger man.
During a “Drew’s News” segment on the Tuesday, Feb. 3 episode of The Drew Barrymore Show, the actress got candid about dating in a discussion with Ross Mathews and Food Network star Sunny Anderson.
“Can everybody remember that dating is supposed to be fun? You know, like, go out and just have fun,” said Mathews, 46, who married husband Wellinthon García in 2022.
Barrymore, 50, quipped, “Can you tell the men I go on dates with that? Because they have lost the memo. I love to, like, date from Psychos.com. I’m not kidding. I’ve had a bad run.”
Then, Anderson, 50, asked Barrymore if she has “tried [dating], like, the 20-somethings?”
“You know what?” replied the 50 First Dates star, “no — I’m totally grossed out by that. No, I have children and it seems wrong now.” Barrymore has two daughters, 13 and 11, with ex-husband Will Kopelman.
Anderson defended her dating hot take, sharing, “Well, you might have tried a 20-something and it didn’t go well. I have tried the 20-somethings and it was fabulous!”
I wanted to talk about this because when I started to hit 30, that was when all of the 18-23 year-olds started to look like babies. When I hit my late 30s, I thought under-27s looked too new, too childlike. Plus, at that point, you’re talking about a generational difference too. Now that I’m 40-something, I’m even more astonished how some “older women” date men in their 20s. Notice I’m not saying “younger men.” If you’re 43 and your guy is 33, I don’t care, y’all probably look the same age too. But 45 with a 24 year old? What’s the appeal in that? See, I say all of that but I do have one exception: there are some really good-looking 20-something tennis players. And Olympic swimmers too. Those are really my only “exceptions,” but I doubt Matteo Berrettini or Borna Coric will give me a call.
Photos courtesy of Avalon Red.
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- SANTA MONICA, LOS ANGELES, CALIFORNIA, USA – APRIL 05: Drew Barrymore wearing Carolina Herrera, Alexis Bittar bag, and Swarovski jewelry arrives at the 11th Annual Breakthrough Prize Ceremony 2025 held at the Barker Hangar on April 5, 2025 in Santa Monica, Los Angeles, California, United States.,Image: 984383749, License: Rights-managed, Restrictions: , Model Release: no, Pictured: Drew Barrymore, Credit line: Xavier Collin/Image Press Agency/Avalon
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- LOS ANGELES, CALIFORNIA, USA – MAY 07: Drew Barrymore of Hollywood Squares arrives at the CBSFEST 2025-2026: Schedule Announcement held at Paramount Studios on May 7, 2025 in Los Angeles, California, United States. Schedule Announcement event to celebrate CBS’ 2025-2026 primetime lineup at the Paramount Studios lot in Los Angeles. The lineup features one new comedy, four action packed dramas, three unscripted series, 18 returning series, sports and special event programming.,Image: 996608945, License: Rights-managed, Restrictions: , Model Release: no, Pictured: Drew Barrymore, Credit line: Xavier Collin/Image Press Agency/Avalon
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- Drew Barrymore attends The 2025 Broadcasting+Cable Hall of Fame Awards 33rd Anniversary Gala at Ziegfeld Ballroom on September 30,2025 in New York, New York, USA.,Image: 1042187257, License: Rights-managed, Restrictions: , Model Release: no, Pictured: Drew Barrymore, Credit line: Robin Platzer/Twin Images/Avalon
Drew will get there lol My friends and I are all in our late 40’s, the separated/divorced friends are dating the 27+ men, and they seem to have a good time. Different challenges with them at times… money and house chores…
But one even left her husband of 19 years to be with her new boyfriend of 28 (during covid, does that make a difference?)
A friend of mine is a legal secretary and there were a lot of divorces post lockdown. Many people found being around their spouse 24/7 very difficult and thought I can’t do this anymore – probably imagining what retirement would look like.
I am in my 50s and anyone in the 20s look sooo young to me, I can’t imagine being attracted to them, other than to appreciate their youthful beauty.
I’m in my 50s and people within 5 or 10 years of my age interest me most.
Everyone younger looks like babies! And what would we talk about? Don’t get me wrong, I have some really good friends who are quite a bit younger than me. But for dating? I can’t see it.
I am also not seeking a Harold to my Maude. For those who want that, there’s a local cougar bar. They don’t advertise themselves as such, but everyone knows which bar it is. I haven’t been but I hear it’s pretty cruisey!
I’m 52, and the only men who approach me are younger guys. Men my age just aren’t hitting on me, so I go where I’m wanted, if you will. My last boyfriend was 15 years younger, but I’m with Drew now – a 20-something seems way too young.
People who aren’t on the dating scene don’t realize how common this is. A lot of younger guys seek out more mature women because we have our shit together (financially and career-wise) and are generally drama-free. *shrug*
I’m 39 and 30 year old men give me the ick, too. It’s gotta be fewer than five years for me. Sorry.
I will say, all the women I know who are dating younger men, it was the younger men who asked them out. Could I see myself dating a 20 something? Not really. Realizing that there are guys that young that I might not turn down? Now that I think about it, yes. But it would have to be a campfire situation. An understanding that it’s probably not going to last long and both parties need to be in better condition when it’s over. (Dan Savage notion.)
IDK my husband is 8 years younger than me and I rarely think about the age difference. He’s just my husband.
We share the same world view, same politics, and have a lot of similar personality traits. I met him when I was 37 and he had just turned 30 and I didn’t really think it would turn serious but it did and very quickly. *shrug*. That being said, I’m 47 now and I really can’t imagine dating someone in their twenties. As Drew said, I would feel gross but that’s just my personal opinion…
If everyone involved are consenting adults then who am I to judge others?
I am in my 50s and can’t imagine dating someone in their 20s. But some of that is about my own insecurity. I am struggling with aging and I think a 25 year old guy would just make me that much more aware of everything I don’t like about my aging body. That part is entirely on me. But reading these comments and seeing that the young guys are chasing the older women makes me wonder if those women are all looking incredible, because plenty do. Or the older women that take those 25 year olds up on the offer may just not be so insecure . I don’t feel attractive so a 25 year old hottie is just going to make that so much worse. No thanks.
I see a lot of women that divorce in their late 40s/50s that say that they won’t ever remarry. A lot of them aren’t even interested in dating men (of any age). My happily married friends even say it, if their spouse were to die or they were to divorce, they wouldn’t want to remarry or even live with a guy again.
I wonder if that mentality plays into these off age pairings? If a woman is 50, doesn’t need a man, doesn’t care about ever getting re-married, but misses romance and having dates, a 25 year old fun, hot guy makes some sense. She’s not trying to marry him, or partner up for life.
This is me, 100%. Happily married for 20+ years, about to turn 49, and if something happens to my husband, I would hang it up. I don’t want to make concessions in my life to another man. We built a life that works for us when we were young enough to figure all of that out together and I can’t see myself doing that again in any way. I would read, cook/bake, enjoy the company of my dog, and annoy my children, lol.
Also, I have an 18 year-old son and I canNOT fathom wanting to date someone closer to my kiddo than myself in age. They’re just completely different beings in totally different stages of life. My son is amazing–smart, empathetic, funny, and wise beyond his years, but he’s still growing and the generation gap is real.
I’m 54 and by the time I was in my early 40s men my own age (+/- 5 years) mostly were only dating younger women and the primary age of men approaching me was 10+ years older or 6+ years younger… So I’m keeping an open mind bc I’d like good companionship. But I do feel like anyone younger than 30 is just a no go for me. It’s just way too young.
I’m so ready for Drew to return to her “Boys On The Side” 90s bisexual era, and just start dating women! Did anyone else see the clips of Robby Hoffman on the show? She was trying to remind Drew that the ladies love her!
SAME. Can we get her together with Audrey Plaza after a sufficient period of grieving, please?
There are some 20 something men that look older than their age or are physically larger where their youth might not be as noticeable (I’m blanking on an example as maybe this is subjective ). Thats the only scenario in which I could see a 50 year old woman being attracted to them (emphasis on the age 50, rather than 32 or 37 where the age difference would be smaller and both people probably look
The same age).
But if the guy is kind of dorky looking like that guy in the new Natalie Portman movie, then Drew Barrymore not being attracted to that makes total sense to me.
An 8-10 year age gap, for people past the early twenty-something range, is nothing. But once it gets past 2 decades, i would think Drew’s reaction (for a woman) is normal.
I can’t imagine being 50 and dating someone in his 20s. When I was 50 my son WAS in his 20s! College-age early 20s, but still. There’s no way.
Younger is fine, but at a certain point I think it would just get too weird. A friend of mine from grad school just had his first child. He’s 59. His wife graduated from college in 2022. They seem happy so, Godspeed. It wouldn’t be for me.
Yeah, I’m 51 and my son is 16. Men in their 20s are WAAAAAY too close to the maturity level of the child I gave birth to, there is nothing less sexy, to me. There’s also that whole pre-frontal cortex thing, and I am just not interested in adding to someone’s “before I was a fully formed adult” stories.
Would you ever hear a celebrity male say that a woman in her twenties was an unimaginable choice for him? Prove me wrong!
Keanu Reeves, probably. But he’s a unicorn among men.