The Downside to Dating Younger Men…

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It’s no secret that I have been dating younger men since my divorce. While it didn’t start out that way, I just found myself in the midst of a bunch of 20-somethings in New York City earlier this year, and I figured, “what the hell?!” and I just went with it. YOLO and all of that.


The first few guys I was romantically involved with right after Chris and I split up were 38 and 39, which was totally fine. Then came a 33 year old in NYC, then suddenly every guy that was interested in me was 28 or 29…then the 24 year old I met while on the Mediterranean cruise. It was a slippery slope of meeting handsome guys in dimly lit bars where they didn’t realize I was “older” to changing my Tinder settings to 25-45…then there was that curly-haired blonde 23 year old in the club in Chattanooga in June that I made out with.

Young men are a lot of fun.


I recently reconnected with a former romantic interest in NYC and he asked me if I could come back to visit for his 30th birthday. Now, in my heart, I was screaming YESSSS! ALL THE YESES! But I knew even then that he and I weren’t going to become an official thing, so I laughed it off and said, “You’re going to be too old for me when you turn 30, babe.” I was kidding of course, but it was the only thing I could think of to decline the birthday invitation without telling him the real reason: I know we aren’t going to last and your 30th birthday is a big fucking deal.

le sigh. Always le sigh with that one.

Anyway, I haven’t specifically sought out younger men. IT JUST HAPPENS. They approach ME.

Exhibit A:


I can’t help it that I am adorable and look like I am 12 years old. Well, the Dysport doesn’t hurt, but I was attracting younger men even before I started smoothing out my wrinkles!

My friends tease me that I only date babies and I always jokingly respond, “But they’re so pretty!!”

And yes, they are pretty. And fun. And happy. I have found that these younger men have less baggage than men my age, and to be quite honest, most of the men my age want younger women. I’ve gone on two dates with men in their 30s and 40s this year, and neither even tried kissing me goodnight, and one asked about getting married and having babies before we even met! He was really nice, and handsome, but…I don’t think it’s fair to waste his time with a third date when he clearly wants to grow his family. That’s just not me. It’s a shame, because he shaved his beard for me for our second date because he knows that I hate facial hair. He’s a GEM.

So, being a single 38 year old is HARD.


I met a 21 year old guy in a bar a while back, and this dude came at me like a HURRICANE. I had zero interest, he wasn’t my type AT ALL…but then he started talking. He thought I was younger, I thought that he was MUCH older. My friends were like “what the literal fuck is happening right now?” It was one of those crazy nights where you end up sitting down at the bar with a stranger and taking notes about his life philosophy and then he introduces you to his brother.

Before I knew it, he was showing me swing dance steps in the middle of an Irish pub and I let him put his phone number in my phone. We hung out all night and he drove me and my friend home and I kissed him. Yeah, yeah…I know, I kissed a 21 year old and that’s kinda gross, BUT he was incredibly mature for his age. Even though he is the exact opposite of my type, we really hit it off and I accepted when he asked me on a date.

That was two months ago. 

After forgetting our date TWO TIMES, me bitching him out and deleting his phone number, then regretting it a few weeks later and reaching out and then him cancelling for a work event, we finally went out this last Saturday. He might be 21, but it was the second best date I’ve had in the year and a half since Chris and I split up. He asked if I wanted him to PICK ME UP FOR OUR DATE, GUYS. We met at a nice bar/restaurant in Downtown Miami and we had such great conversation that we never even ordered dinner.

And he turns 22 tomorrow, which makes it all that much less disgusting, right? 22…38…

How old was Demi Moore when she started dating Ashton Kutcher?

Did I mention he is former military, in a foreign country?

Military = bonus points, right?

Anyway, this guy is pretty awesome, but clearly, there’s a 16 year age difference and I am smart enough to know that it’s going absolutely nowhere. We will probably get together for drinks a few times, make out a lot and then I’ll become his older friend that he invites to his wedding out of pity, hoping I’ll hit it off with one of his older cousins or uncles or something.

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