How to Determine Whether Your Dating Age Gap Is Embarrassing

Advice from three of our guy friends. This week, a straight woman asks, “How much younger than them do you think most guys are comfortable dating before it becomes embarrassing? Or is there no limit as long as the youngster in question is legal and not a complete airhead?” To ask the guys your own question, click here.

Gay Single Guy (Jay Dyckman): Yes, there is an age too young for anyone to date. But I think it happens only after you hit 35. Any dating combo of two people both under 35 (provided both are over 21…yes, 21, not 18) is probably not a big deal. No one really considers themselves that old before hitting 35.

After 35, all bets are off.  If you’re over 35 and you date someone more than 10 years your junior, you will — and rightly so — be mocked (and silently envied) by your friends and enemies for such dating hubris. It will put you squarely in the “oh please” zone. And this goes for both men and women: Dating much younger than yourself connotes a power dynamic that is creepy yet totally gender non-specific.  Both sexes look entirely ridiculous parading their toy around, be it male or female. But if you’re over 35, you can date anyone  — of any age disparity — who is also over 35.  A 65-year-old and 37-year-old?  Sure, why not.

This might seem arbitrary, but age designations exist for a reason. The good people of corporate America have decided that once we’re older than 35, we are no longer a desirable marketing demographic.  That’s real science, people. After 35, big age differences are obviously apparent, but both parties have fully exited the nubile stage so no one really cares. You are no longer hip, cool, or capable of dating someone who had a “The Voice”-themed Bar Mitzvah. That’s not to say you shouldn’t do it.  Hell, if someone of the Gen Next persuasion wants to tap your old bones, consider yourself lucky. Besides, anyone who mocks you, well, your old ears won’t be able to hear them anyway, so who cares.

Straight Single Guy (Tyler Barnett): For guys in their twenties, like me, up to guys in their mid-thirties, I think the lowest we should go is 21. If I cannot legally have a glass of wine or cocktail with a girl, I don’t want to date her. It’s not that I am some sort of alcoholic or can’t have a good time sober, but there’s something sexy and intimate about sitting in a bar that cannot be substituted by Starbucks or Jamba Juice. It also makes me feel like an old man if I am with someone that has to use a fake ID to buy a beer. Besides, if the girl in question is still in school, the conversation will usually leave something to be desired due to her lack of life experiences and responsibilities — it’s hard to listen to tales of college papers when I’ve got bills to pay and employees to manage, you know? There is a lot to be said for being in the same place in life, age-wise at least.

But generally, I think women a good five years younger (so long as they aren’t under 21) work well since women tend to be more mature than us guys. For an older man, say in his forties or fifties, a fifteen year age gap is socially acceptable and generally comfortable. And I think once a woman passes the age of thirty, up to a twenty year difference with an older guy is just fine.

Straight Married Guy (Jim): Come on, give us guys some credit: most of us know there’s a huge difference (emotionally, intellectually, maturity-wise) between someone around our own age and an 18-year-old with AP credit.  She’d have to be a Rhodes Scholar studying quantum physics if the difference in their ages was more than about 25% of his. So, what does he teach?



  1. I’m 24 and dating someone who is 32.i don’t think age is an issue. I believe it has more to do with your maturity level. I would rather be able to have an intellectual conversation then Talk about drama.

  2. I am 32 and I dated a 25 yr old guy last year for about 3 months before realizing that having an advanced degree and a title doesn’t equal maturity across the board. He was a LOT of fun in the bedroom,and could be very gentlemanly, but way too caught up in himself and his schedule. Dr. Spontaneous could never plan anything more than two days in advance and ultimately, it was over.

    However, I also dated a 39 yr old MD, and he had similar immaturity issues…and can’t seem to decide whether to stay friends or pursue a relationship. Age really is just a number.

  3. Sure, large age gaps have only a small chance of making it long term, but it’s a good sign if they can joke about it being creepy. Anyone who truly makes an issue of it should be told to shove it. Happiness is too important; buzzkills are poopyheads.

  4. Johnny used the formula! 1/2 + 7, It’s science!

    As a divorced dad of a daughter I always had my own creepy gauge that I had to navigate. Now that I’m 50 and my baby is 23, if I even thought about dating a girl close to her age she’d kill me!

  5. Really like Jay’s answer.

    Another way to calculate this is the generally accepted formula (age/2+7).


    … of course, I could care less? If I were single, I’d have sex with any woman over the age of 19 (just for a nice safe buffer zone – I’m too poor at math to look at a girl’s id and calculate in my head if she’s actually 18). What are you gonna do, laugh at me? Call me a creep? Imply that I can’t handle a “real woman”?

    PPFFF! Go ahead and talk shit. I’m sure all the 40 year old guys with 20 year old girlfriends are crying all the way to the bedroom.

    There was a time homosexuals were ashamed to go public because people would call them creepy and gross. Why should anyone else be shamed for their perfectly natural, perfectly legal sexual desires? Date as young as you want.

    If a guy who prefers youth (pretty much most) and a girl who prefers age (a not uncommon fetish) want to get together, why should disapproving glares stop them?

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