How To Date Shy Men


I realize most women find confidence attractive. I’ve seen men who have no chance of bedding certain women overcome daunting obstacles—height, weight, hair plugs, Hawaiian shirts—with attitude. I find most of these men to be detestable braggarts. Perhaps, you do as well. Maybe that’s why you prefer quietly secure men.

I applaud you with a golf clap.

Now, what you need to realize before entering such an arrangement is that this man will need to be led. If you sit back and wait for him to make moves, you’ll be lulled into slumberland. Here’s a list of things you had better be comfortable doing:

  • Approaching the man who interests you.
  • Suggesting the date, time, and place of your next date.
  • Placing his thumb on your clit while in girl-on-top position. (Note: This is an advanced technique, enjoyed by many, mastered by few.)
  • Giving him what he wants without asking him.
  • Defending him to your friends who will suggest he may be in a walking coma.

These wallflowers are easy to find if you seek them. They tend to blend in with shelves, lampposts, and shrubbery. Scan the perimeter of whatever venue you happen to be working for men with hands in pockets, and expect lack of eye-contact.

Once targeted, approach him as you would a timid fawn. A fistful of beer nuts might help. A fistful of Astroglide might be a bit too forward.

Side Note: What’s with the latest trend of women spitting on or licking their fingers, then wiping it on themselves prior to entry? Isn’t there a better way? Most men don’t like seeing or hearing women spitting. Perhaps it would be better to excuse yourself to the powder room to grease up the gears. Heck, you could have a Jiffy Lube drum and pump in there for all we care. Just stop spitting. Yuck!


You’ve gotten your wallflower cornered. How do you close the deal? Always leave him a path of egress. If, at any point, he runs away screaming, just shrug him off and move on. Some guys are just too much work. If he stays, makes intermittent eye contact, giggles, and says cute things like, “Aw, shucks,” you’ve won him over. Show him you’re willing to drive this train. Take him by the hand, interlock fingers, ignore the sweaty palm, and lead him to the bar. Don’t ask what he prefers, just order two chilled shots of Don Julio. Lick (it’s OK to do this now) the back of your hand and his hand, sprinkle salt, lick again (exception number two), throw down the shot, bite your lime, and throw it. If you’re caught, say it slipped.

Two or three of these and shy guy will loosen up like waxed shoelaces. Before you know it, he’ll be hooting, howling, and riding you like he’s drilling for oil. Tomorrow, he’ll apologize, and need therapy. Give him a punch in the arm and say, “You’re forgiven. Job well done.”

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About the author

Author of humorous essays about relationships and lifestyles.