Dating Survival Guide: The Older Gentleman

As much as we tend to value youth and beauty, there’s a certain allure to age.  You’re hot for gramps, but find yourself feeling tongue-tied and bashful over your age difference.  Never fear, the dating guide is here: with these few tips, you’ll spend less time worrying about the age gap and more time filling other gaps. Heyyyy!

Due to women being more emotionally mature than men, an older man dating the younger woman is not a rare thing.  (Okay, women act like morons, too, but I’m speaking to the Comediva audience, a coterie of learned ladies who use words like “coterie.”  Wink.)  At any rate, the uneasiness you feel at dating someone who was in college when you were in diapers is most likely just you.  Expose that youthful, elastic skin, bat those doe eyes, and show off your fabulous legs, and most older men will be chomping at the bit to get in on your fountain of youth.  This guide will help you maintain conversation when you’re out of the bed, and keep you from making him feel like a pedophile.

Cheat Sheet
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Classic Movies:  You can prove yourself an “old soul” with easy conversation about films beyond your birthdate.  If you’re a movie buff, this will prove especially easy, and odds are you’ve seen a lot of movies as a kid on VHS (Or, you know, streamed over bittorrent … if you’re way younger) that he saw during their original release.  Star Wars, anyone?

The Beatles:  A 14-year old kid I tutor has some Abbey Road on his iPod along with Lil’ Wayne.  Some music’s just good … so you can talk about it without making him feel dated.

Neutral Territory:  Once you’re past 18, you’re fair game.  If you can get tried as an adult in court, fuck any other consenting adult, and also do things like vote, live in your own apartment, and pay taxes.  The doldrums of adult life don’t really change much with age, until you get into aching bone territory or are nursing babies.  So, talk about it: news, politics, philosophy, entertainment … plenty of things remain eternally engaging.  Like traffic sucking, or burgers being delicious, there’s a lot we can all relate to.

Get Schooled:  Similarly, being over 18, you’ve probably gone to school and have your own interests that stem past what’s trending on Twitter.  He’s got a lot of years on you, but don’t sell yourself short: surely you know a thing or two that he doesn’t, and he’d probably love to hear about it.  Tell him about your trip to Peru, or the fascinating article you read, or your dissertation on the migratory patterns of Canadian Geese.  (Well, maybe not that one.)

Potential Minefields
Texting:  Take it easy with the MMS, lest your gent be less than text savvy: keep your spelling normal and your ROFLMAOs to a minimum, and pick up on cues: if he’s not an avid texter, opt for a phone call, or he may associate you with his Blackberry-crazed teenage daughter.

Hipster Joints:  Don’t take him out to places overrun by 20-somethings.  It will make him feel ancient, way out of place and uncool, and he’ll spend more time marveling at the young men’s ridiculously deep v-necks and facial hair than enjoying your company.

Pop Culture:  You’re totes allowed to tweet and keep up on your fave shows, just be aware he probably isn’t into that as much.  Avoid gushing excitedly over the leaked footage from Breaking Dawn and keep your belting out of Ke$ha to a minimum, regardless of irony.

Inadvertent Year References:  Unless you’re specifically trying to tease him — which can be fun — steer clear from calling out the reality of actual dates.  For example, when he mentions his high school graduation in the 80s, maybe don’t say, “Man, I was two!”  It’ll creep him out.  Or make him feel aroused.  But that’s weird.

Family Photos:  If you see an old picture that looks like him, resist asking, “Is that your Dad?” because it’s probably him.  It’s the ageist equivalent of asking a chubby gal if she’s pregnant.

In conclusion, so long as you like the man, it doesn’t really matter how old he is, if you get along.  And dating older does have its advantages: by this point, he’s probably seen A LOT of vaginae, and you’ll reap the benefits of that life experience.  (Plus, he’s probs gonna die, like, way before you.  So enjoy it while you can!)


You taste like Louis Vuitton!


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