Can Women In Their 30's Dating Men In Their 20's Ever Actually Work?

It's all fun and games until someone wants a baby and someone is acting like one. 

Khloé Kardashian has hopped on the younger man train. The 32-year-old has been dating Cleveland Cavaliers center Tristan Thompson since last month. The new “it” couple was spotted holding hands in Miami this past weekend, and Tristan has been “mom approved” by family matriarch Kris Jenner, who told reporters at the recent Brent Shapiro Foundation for Drug and Alcohol Prevention Summer Spectacular in Beverly Hills, California that the two are “really cute” together. “You know, she's having a good time, he seems like a really nice guy,” Kris said.   

Khloé and Tristan shared a kiss on Snapchat in Miami over the weekend. And while Khloé has been through a marriage already, Tristan, at 25, is seven years younger that her.

Dating a man nearly ten years younger may be new territory for Khloé , but if she has any qualms about it, she can just turn to Amy Schumer for advice—well, maybe not after that Saturday Night Live monologue. But anyway, The Girl With the Lower Back Tattoo, author has been dating Ben Hanisch, a furniture designer out of Chicago, since late last year after meeting him on a dating app she joined for just 48 hours. The comedienne is 35, Ben was 29 when they started dating. He just turned 30. The two have gotten serious; they’ve moved in together, and Amy has said that the two are crazy in love.

I love the man in this photo and Ben too #lawrencefishburneforlife

A photo posted by @amyschumer on

"There used to be a real stigma of an older woman being involved with a younger man, but nowadays, there's a lot more of seeing people as equals," says dating and relationship coach Fran Greene, author of The Flirting Bible. So these relationships shouldn’t even give anyone a second thought, right?

Think again.

While the difference over the number of years is minuscule, there can be one major age-related roadblock for this particular May-December pairing. “They may not look any different together, but their minds are worlds apart,” declares Fran. 


“A woman in her thirties may be thinking about marriage and children and wanting to put those life goals on the fast track before 40,” she says. 

For the millennial still in his twenties, “He may be thinking, ‘I’m young and have the rest of my life to find the women of my dreams, so I don’t have to do it right now.’” If this becomes a major issue, these relationships may stall and fizzle out. 

Fran theorizes that wouldn’t be the case for a woman twice as old as her twenty-something lover. 

“A woman in her forties or fifties may have already been married and had children. She is not necessarily thinking she is going to marry her youthful paramour, but is happy to enjoy his company in the moment,” (if she hasn’t turned into her boy toy’s mama.)

There is a silver lining for a woman in their thirties dating a man just a few years her junior, according to Schumer. "We love having sex with each other,” she exclaimed during an interview on Howard Stern’s SiriusXM satellite show, revealing that she and Ben have sex every day, even if she claims she lays there like she’s getting a CAT Scan.

“That’s because they both still have the stamina,” Fran laughs.

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