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Hot Dog and the Lady Bun – Age Differences

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We answer your pathetic questions about dating, loneliness, and your inevitable failure.

Dear Hot Dog and Lady Bun,
I’m dating a much older man who treats me great. The problem is that he’s really putting a damper on my social life. He gets too tired to go out and wants to do boring things all the time.

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Hot Dog Grows Old With You

Dating an older woman is great, mainly because women under 29 are clinically insane (the DMV classifies it as “Born After Who’s the Boss Went off The Air Syndrome.”) An older woman gives you the best of both worlds: sexual maturity combined with the illicit thrill of sleeping with a woman your aunt’s age. But bedding an older woman is sometimes a tough thing to pull off—mainly because younger men are often as attractive to older women as is a chimpanzee with a learning disorder. But the thing you have to look out for in any age gap relationship is power differentials—older people are often “wiser” and “less continent.” Here’s a few ways to keep things on equal footing when you’re having Good Times with Great Oldies:

  • Next time she wants to go to bed early, don’t argue, just softly sing the Golden Girls theme song all the way home.
  • Make “Statutory Rape” your safe word. The older you are the funnier this is.
  • In the morning, put googly eyes on your penis and wake her by saying, “Hey grandma! There’s an early bird special for this little worm!”


Of course communication can sometimes be hard when there’s a big age gap; especially in an age where younger people communicate primarily through texts and social networking, and older people communicate solely through faxes and renting beta-maxes. Here’s a few ways to make sure you’re both on the same “page” about who’s “closer to death”:

  • “Was this song popular when you were a kid?” (Bang two stones together repeatedly.)
  • “You really remind me of my mom. Which is not creepy! I breast-fed until I was five. I love older women’s tits.”
  • “What I love most about us is that since women live longer than men, we’ll probably die on the same day.”


Lady Bun Ticks Your Tock

The dating world has created an environment where older men age like wine and older women age like milk. Much of the reason men are attracted to younger women is because the words “life experience” and “maturity” makes boners softer than diarrhea at a Bon Iver concert. Older men want the thrill of dating a nubile lady without the hassle of having to post photos of their meals on Instagram. The only way to make the generational differences work here is to meet him in the middle, the way his balls do with his knees. It may be unsexy and monotonous at times, but hey, so is The Gap and those fuckers have been selling khakis since before you were born. Here are ways to ease this old-timer into some fun-timers.

  • Another boring movie night? How about suggesting you watch Transformers and then telling him it’s about an old, shitty robot that turns into a cooler, sexier robot when he goes to bars.
  • Try spicing up another dinner at home by cooking something exotic at his house, like Vietnamese food or meth.
  • Trouble with his libido? When he comes home from work, surprise him with an irresistible trail of Werther’s Originals® leading straight to your beaver.


Now that you’ve tried to make the most out of his golden years, it’s time to get him where it counts: His soft brain. Try to connect with him via verbal telegraph by sending him the kind of signals that lets your salt ‘n’ pepper sire know you’ll be with him till he retires (i.e., not long). 

  • “Your eyes tell a story… Like the Dead Sea Scrolls or cave paintings.”
  • “Age is nothing but a number, but your number gets you discounts on the bus.” 
  • “You’ve taught me things I could never learn in school—mostly ‘cause my college didn’t have courses on Alan Alda and Cialis.”


Previously – Wandering Profile

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