Sasha Speaks: Answering Your Most Private Dating Questions –- Help I’m Shy and Dateless?

  • Posted on: November 15th, 2010 by

Sasha Speaks 11.15.10

Dear Sasha,
I’m 20 and I have never been on a date. It’s not that I don’t like girls, I actually think about them all the time. The problem is that I’m beyond shy, to the point of becoming a deer in the headlights anytime I even try to approach a girl to talk to her. On campus, in social settings with my guy friends, and at work, I freeze up.
What’s a shy guy to do?

Deer-like guy

Oh, you dear deer, you.

Don’t fret, my pet; being 20 and not having gone on a date isn’t that big of a deal. I didn’t have my first serious boyfriend or lose my virginity until I was 22, and neither did a lot of my friends, so I can tell you with full authority, good things come to those who wait. Besides, the rules of dating and sex have totally changed in the new millennium; it’s not like you need to have your pin on someone by the senior sock hop nowadays.

The biggest battle you’re facing is internal, so what you have to remember is this: Don’t psyche yourself out. I’m sure the prospect of approaching women is daunting but the Catch-22 is, the most attractive thing a man can possess is confidence.

When a guy walks into a room and acts like he can get any girl, he usually can. Take for example that schmuck The Situation on Jersey Shore. He looks like an overbaked, steroided out Popeye. And he wears Ed Hardy! There is NOTHING attractive going on in that equation. But he gets tail right and left. Why? Partially because he’s on a TV show, but, more importantly, because he’s confident. Swagger makes any man exponentially more attractive.

Shoulders back, head high, if you can talk to a girl like you’re already thick as thieves, she’ll be putty in your hands. Ease and self-assurance are the names of the game.

So how do you achieve that?

Don’t go with the old “Picture the person you’re talking to naked” trick, because chances are you’re already doing that and it’s one of the reasons you’re so overwrought. Instead, I have a quote for you to memorize.

My friend’s dad is an old Marlboro Man-type cowboy from Texas and he gave me the best piece of advice I’ve ever heard when it comes to feeling intimidated. The next time you’re starting to freeze up, let these words ring in your ears: “Everyone’s face turns red when they’re takin’ a big sh*t.”

Gross, but true. Take a few deep breaths and remember that these girls are just people like you and me, no better or worse.

Good luck!

*Feel free to email us with any dating, relationship, love and sex questions you may have for Sasha.

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About Jennifer

Jennifer Kelton

Jennifer Kelton CEO / founder LLC is a Los Angeles native and a pioneer in the worldwide dating industry, investigating the game of love while providing encouragement and support since 2007, starting with the acclaimed dating book Don’t Use My Sweater like a Towel. An accomplished CEO, visionary and entrepreneur, Kelton’s work in the […]

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