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I am 23 years old, have never had any problems attracting men, but somehow I have developed a crush on my boss’s brother, who is 52 years old. I have heard that older men make for great lovers, and this is part of the attraction. But mostly, I love the attention he gives me, the hugs, the smiles. He makes me feel “real.” Is it real? If you don’t agree, aren’t my feelings real? — Jennifer S.
Age-wise, I’m right in between you and your boss’s brother. I’m 39 years old, though as Kinky Friedman would say, I read on a 40-year-old level. Studies that I’ve fabricated have shown that men over 30 are, on average, better lovers. Part of this comes from just having logged more sack-time. Peer-reviewed scientist Malcolm Gladwell holds that if you want to become a master at anything, you must practice it for 10,000 hours. (Including time spent practicing on my own, I’m at about 14,000 hours, so I’m both proficient and really, really chafed).
But part of older men’s bedroom mastery also comes, of course, from the gnawing realization that their virility is fading. This means that they’d be eager to please you out of desperation and defiance of their age, and because it might be their last chance to ever sleep with a woman in her early 20s. You’re not a mere object of desire, you’re a nostalgia ride. They count on you being too young and naïve to notice this. If they wanted someone who saw all the angles, they’d sleep with someone their own age.
Which brings us to this “realness” you speak of. Without knowing you, I can pretty much guarantee that the feelings are real. Though I imagine your definitions of realness might differ. His “real” is likely the feeling he gets in his pants whenever he’s doing all this hugging on you. Then, as they say in Iraq, the surge is working. Whereas your real is being showered with affection by a man with a little seasoning and with decades-more practice faking the sincerity that women find so endearing. Is that enough to sustain something beyond a brief, uncomfortable fling that could wreck havoc in the workplace when your boss finds out you’ve taken up with his brother? I can’t say for certain. That’s between you and gramps.
Personally, I like a woman with a few road years on her odometer, which is why on the rare occasions when I step out on my wife, it’s usually with septuagenarians and up. I get a woman who knows her way around the chessboard, plus, we get the seniors’ discount when we go to the movies. But I’m not turning to her for sustained companionship, just for sex and for evening movie tickets at matinee prices. You should have similarly realistic expectations. Also, remember that if this crush becomes a relationship, and you actually fall in love, when you’re 52, he’ll be 81. Hard to get much realer than that.
I think the government is watching me. Will a tinfoil hat help? — Stephen
No. Its shininess draws the eye. Plus, its heat-conducting properties will cause you to perspire, making you look more suspicious than I suspect you already do. If you really want to go underground, I suggest hosting your own show on CNN. Nobody will find you there.
What’s your dream duet scenario, and what kind of song would it be? — Joel S.
Oh Lord, that’s a tough one. There’s so many talented kids on the scene today that I wouldn’t mind doing a Tony Bennett-style duets album with. You’ve got your Selena Gomez. Your Ashley Tisdale. And it would be an honor to sing with even an untalented Jonas Brother. (Psych – all the Jo Bros. are talented!) Though you have to put Justin Bieber on any short list. That kid’s got swagger. Which he should, since he has a “swagger coach.”
If forced to choose a duets partner, however, I’d probably scrap all the teen meat, and start a cover band with Rep. Michele Bachmann. Succumbing to headline hackery, we’d give the critics what they want, and call ourselves Michele Bachmann Turner Overdrive, playing classic rock anthems at Tea Parties and Bar Mitzvahs throughout the land (even though Michele is Lutheran/Norwegian, after she said that America would cease to exist if we don’t stand with Israel, she’s huge with the Jews). I’d have to legally change my name to “Turner,” of course, so that our act’s name made sense. But it wouldn’t be after Fred Turner, BTO’s bassist/vocalist. It would be after Ike Turner, because that’s the dictatorial way I’d run this band. With Michele as my Tina, I’d tell her what to sing and what to wear (something short, tight and sexy, it goes without saying).
We’d do all the crowd-pleasers—“Takin’ Care of Business,” “You Ain’t Seen Nothing Yet”—but we’d save our signature number for the encore, because I believe in making the fans beg: John Ashcroft’s “Let the Eagle Soar.” What’s not to like about that tune? It’s patriotic, it’s easy to sing along with, and it’s about an endangered species. It probably should be our national anthem. Either that, or Justin Bieber’s “U Smile.” That little moppet might be Canadian, but he understands what America’s about.
All too frequently, I get heckled by motorists when I go cycling around town. What is the best response? I’ve thought about spraying them in the face with pepper spray. Good idea or not? — John
It’s a great idea, John. I’m all for pepper-spraying people, particularly the ones I don’t like. It temporarily incapacitates them, causes no permanent injury, and it makes them useful if you want to rub their face on your salad. But what if the offending motorist’s window is rolled up? What are you going to do then? Spray it through their vent ducts? You need a more practical solution. I suggest taking a page from the Jim Treacher playbook, stopping in front of their moving vehicle, and kneeing their car as hard as you can. If you’re a real man like Treacher, that is.
If not, stick with girly pepper spray, and those ridiculous bike shorts you cyclists favor. Nothing says “heckle me” to mischief-making drivers like a man’s lycra-clad buttocks waggling in their faces. I suggest going with looser-fitting cotton. What you sacrifice in mobility, you’ll regain in self-respect.
Matt Labash is a senior writer with the Weekly Standard magazine. His book, “Fly Fishing With Darth Vader: And Other Adventures with Evangelical Wrestlers, Political Hitmen, and Jewish Cowboys,” is just published from Simon and Schuster. Have a burning question for Matt? Submit it here.