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The Dos and Don'ts of Dating Someone Younger

Everything you need to know about music, politics, sex and food additives

By Peter Gerstenzang

If you’re anything like me, in the near future, you’ll probably find yourself dating someone who is younger than you. There are, of course, any number of reasons for this. But it’s mostly because there just aren’t that many people who are older than you, unless you want to go out with someone eager to tell you about her part in the Cuban Missile Crisis.

So, fellow boomers, I’ve come to your rescue. Having recently dated a women so young she couldn’t name Jakob Dylan’s father, I’ve put together a how-to list featuring all the things you need to know about conducting yourself with members of the younger generation.

P.S.: To achieve gender equality, I wrote the first half of this wearing pants, the second half in culottes.


If you’re dating somebody younger, you’ll definitely need advice regarding your musical references. This is crucial when it comes to knowing the names of all the big festivals and employing them correctly. For example, if you toss out Lollapalooza when you really mean Coachella, this may blow up in your face.

Make sure, too, that you get your jam band names correct. Do not say Umphrey’s McGee when you actually mean The String Cheese Incident or the night will come to a screeching halt. Do not confuse Jack Johnson with Ben Harper, or you will not get a second date.

Want a couple of terms that will always keep you covered? Just remember that young people call records “discs.” And that you can respond to almost any question by saying “Radiohead.” Learn these two rules and you’ll be fine.

Food Additives

Young people today are obsessed with food additives. So know this about going out to dinner: Anything you order likely will be met with your date’s prediction that it’ll kill you by the end of the week.

The younger crowd is especially enraged by something called GMOs. If you want to get in good with your new squeeze, you’ll want to work GMO outrage into the conversation. If you don’t want to blow it, be sure you use the term correctly. In other words, should you say the GMO is still your favorite muscle car, expect that to be followed by a bone-chilling silence.

Your Age

People over 50 often wonder if they should reveal their age when dating someone younger. I would have to say yes. Mostly because, after 50, your memory starts to go. And lies about your age become just too hard to remember.


In other words, your story may start out that you like The Grateful Dead. Then shift to, you saw The Grateful Dead. And finally, that you were in The Grateful Dead. It all goes downhill from here. So, yes, tell the truth about your age.


Yep, you still want to engage in it. But remember, a younger partner will have a distinct advantage in this area. Still, you can even up the odds by utilizing the nap. If you know you’re having sex that night, take a nap before. If you’re going to be engaging in more than one bout of sex, take a nap afterward.

You can do almost anything, except take a nap during. That is worse than lying about your age.


If you are dating a young Democrat, use the word “agribusiness”  as much as possible. They love that. And, if you follow it with GMOs, that’s as good as a double word score. If you’re dating a young Republican, you can always go with “smaller government.” That’s an evergreen. If, however, you find you’re dating a Trump supporter? I got nothing.


This is one of the more explosive parts of the May-December relationship. Because it has to do with reading. An activity so archaic, you might have to give your lover a book about the history of reading. Which may be a problem when they can’t read it. And you may then have to act the whole thing out with an interpretive dance.

Still, there are ways to get your date interested. Say that Don Quixote is the story of the dude who was once head of the Mafia. That Native Son is a mystery about where Ted Cruz was really born. And that The Great Gatsby is a novelization of that movie with Leonardo DiCaprio. Then, hope that really good sex makes up for the entire thing.

Peter Gerstenzang is a humorist, video director and journalist. Read More
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