Dating Younger Men Who Bemoan “Pushing 30”

I’ve never really hesitated about dating younger men. If you asked my friends, they’d probably tease, “Oh yeah, Mary Lane has a thing for younger guys.” 

Which is true, if you subscribe to a myriad of dating clichés:

Women Prefer to Date Older Men!
Men Prefer to Date Younger Women!

Men Are Immature Compared to Women Their Age!

Women Who Date Younger Men Are Cougars! 

Yuck. I’ve found as much truth in those cliches as I’ve found inaccuracy. I call it a wash. Am I an expert? My friends, again, would tease, “Yes!” My sample pool is not exactly scientific, but I can claim to having dated just as many men who were younger than me as I have men who were older. 

Let’s play a little game, called:

Was He Older or Younger Than Me? 
(Take a guess! No cheating!)

A. The guy whose parents still paid his rent. 

B. The guy who got black out drunk every single weekend.

C. The guy who cheated on me and I found out by reading his diary. 

D. The guy who had his own car, an adorable dog, and a beautiful back yard. 

Did you write down your guesses? Recognize any of these stories from blog posts past? Ready for the answers?


A. OLDER: I was 22, he was 29.

B. OLDER: I was 28, he was 34. 

C. YOUNGER: I was 24, he was 19. So no surprise there. It’s also a great story and you don’t have to take my word for it cause I blogged the shit out of it. 

D. BOTH. I dated two very different guys who fit this description. One when I was 26 and he was 23, the other when I was 27 and he was 34. 

Take from this game what you want. In my experience, not all younger guys are immature and not all older fellas have their shit together. Shocking revelation, I know.

Age is just a number, goes the cliché.

Sometimes an age difference of 4 years feels like nothing. Other times an age difference of mere months feels huge.

Like when you’re in 9th grade and dating an 8th grader. That’s the difference between middle school and high school. Between popularity and social suicide!

Or when you’re 22 and dating a 20 year old. That’s the difference between social drinking and social suicide sobriety. 

When you’re 30 and dating a 29 year old. That’s…that’s really no difference at all. But I was on a date with a 29 year old old last week, and suddenly that one year felt like a huge difference. 

dating younger men 30 bemoan

It was the day before Valentine’s Day, we sipped white wine at a bar in Greenwich Village. He was cute in that cliché Clark Kent way, with wire rimmed glasses and well cut hair. It was a Monday night, we were sharing stories from the weekend.

“I was completely useless yesterday,” my date said, “A horrible hangover and it really knocked me out. Can’t drink like I used to, you know? Makes me feel old. Suddenly I’m pushing 30 and it’s like, I can’t drink any more. ” 

I smiled and nodded, probably offered some anecdote about a killer hangover to commiserate. But I kinda wanted to roll my eyes and tell him to shut up. I didn’t, but this conversation stuck with me. 

Why talk about feeling old on a date? Joke about it ok, but you better be funny. If you’re not, I’m left scratching my head. Why would you talk about feeling old, “pushing 30”, to your date WHO ACTUALLY IS 30? I don’t get it! 

My mind is boggled and annoyed. Like it usually is when a double standard is staring me in the face, sipping wine.

Hey hey hey! Men get to talk about feeling old on a date without a second thought! Haha! Isn’t that cute?

Can I even IMAGINE a world where I could casually chat about “feeling old” on a date? FUCK. NO.

A world with time travel and talking animals seems more realistic! Everything I’ve ever read, heard, watched, lived, KNOWN tells me exactly what to expect if I even hint at feeling old on a date. Ever so vaguely hint! Or joke about feeling old. The most blatant, hilarious, I’m-clearly-kidding joke!

A woman expresses, “I feel old” and her date’s genitalia recoils, shrivels up just like Jack’s did when he hit the water in Titanic. The pee-pee hole becomes a mouth, emitting a terrified scream, like the terrible sound a rabbit makes only when death is imminent.

Mention you feel old as a woman and the heavens part. Your fairy godmother descends to earth, amid a shower of anti-aging cream. Does she make you a dress and take you to a ball to meet a prince? NO, BITCH! Your fairy godmother flies to earth to SLAP you HARD in the face with whatever single gal self-help book is currently on the best-seller list. No Bippity Boppity Boo for you, just a simple, harsh, “ARE YOU TRYING TO DIE ALONE!?”

You asked why I marched? This. This is why.

That’s a joke. Kinda. Sorta

I’m sure some would say to take my date’s conversation as a complement. Like how if someone complains about feeling fat to you, they must not think you’re fat! He complained about pushing 30 so he must not think I’m 30! How nice! 

He saw my online dating profile where a big 3-0 boldly is typed next to my face. He knows I’m 30! Dude’s just a dummy.

Maybe that’s not fair. It’s not my date’s fault this was my thought spiral. I didn’t tell him any of these thoughts…confrontation doesn’t belong on first dates. I shared these thought’s with you, dear reader, instead. Because I had to tell someone. 

Tell me I’m overreacting. Tell me this is just dating in the age of Drumpf. Maybe tell a story how something similar happened to you too? If you know a story of a woman who complained about feeling old on a date, that I need to hear!
You can totally tell me I’m crazy for dating younger dudes…Tell my if the love of your life a dude 4 years younger than you or a lady 4 years older? Please share! Really, tell me whatever your thoughts are after reading in the comments below. Or you can pop over to my Twitter or Facebook.

Thanks for reading!

About New York Cliche

NYC lifestyle blog by Mary Lane. Events, adventures, epic mistakes, dating, life, humor. A 20-something trying to make it (and make out) in the city of dreams.

10 thoughts on “Dating Younger Men Who Bemoan “Pushing 30”

  1. My first boyfriend was a senior and I was. Sophomore. I thought it was so cool until after we broke up. I could not fathom dating. Sophomore when I was a senior. I’m told I’m mature for my age, but still. It was weird one I got to the older age! I figure you need someone who is the same maturity as you and in the same space as you, no matter the ages. 😊

    Breanna Catharina
    Breanna Catharina recently posted…004: LightMy Profile

    1. Oh yeah, a couple years is huge when you’re still in school! Esp because everyone’s life path is so similar during those years- gets a little different a couple years past school for sure! When some people have careers and kids and others are still figuring it out! And all in between!

  2. Oddly enough my first roommate is in a serious relationship with a man 15 years Her senior. However, I feel like that compounds on the fact that it’s totally cool for guys to trade in an “older model” for a new one. 😤As a woman the age bias has always bothered me. For one, I feel like society deems the aging woman as unattractive and less valuable than a younger Lady. Not to mention, after having a stroke I felt like years(I should’ve had)were slipping away from me. Suddenly, I was keenly aware of anti-aging creams and regimens. Trying(likely futilely) to stop the forward march of time.I’m also now 33 and dreading that number getting any higher!😭

  3. Maybe it was a trap! Maybe when he said “pushing thirty,” he expected you to giggle childishly and say something like, “Oh I wouldn’t know anything about that! I’m 22! I only put ’30’ on my dating profile to scare away creepers, but not YOU, you’re a NiceGuy! Also, I never want babies, hate the concept of marriage, and love three-ways with other girls! I’m such a CoolGirl teehee!”

    Alas, probably not, but I love to assume the worst in people when dating. It saves time.
    Meghan Sara recently posted…Good News! I’m back from California, and I brought the sunshine with me (as well as some rocks)!My Profile

  4. I used to care SO much about age (younger guys = super immature = no thanks) but I’m now learning that immaturity comes in all ages, shapes and sizes. I’ve met 29 year olds with good jobs and heads on their shoulders and I’ve met juvenile 39 year olds. I once went out with a guy pushing 40 and I asked if he’d every been engaged or married and he said “ew.” EW. I really do think age ain’t nothin’ but a number and it’s all about the individual person. To me? Be a man, be respectful and mature when you need to be — silliness is welcomed but don’t drunk dial me, get black out drunk or act like a childish horse’s ass. Then we’re good. 🙂

  5. I once met a man in New York, he said he was 39, but online said he was 47. He kept saying he was 39. He’s since he’ll out with me and told his real age. Kind of kind I miss his phone calls.

    The older you get, the harder it is to find someone who’s not been married before or had kids.

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