How To Ask A Shy Girl Out On A Date…


Nothing can be more intimidating than asking out a girl you’ve had a crush on or have known since forever.  The thought of telling this amazing woman that you really like her and having her snub you sends shivers down the spine, especially if she’s shy.

It doesn’t matter how popular or confident you are, when it comes to that special girl it’s hard to find the right words. You don’t want to put her off, but what is the right thing to do?

Dear Dan and Jennifer,

I’m a good looking, popular guy and have no trouble asking girls out – except for this one girl I’ve had a crush on since the eight grade… I walk away from a conversation with her thinking “What the heck did I just say” – I sound like a dumb jock! My Question: How do you ask out a shy girl, that you are desperately head over heals in love with? Ask her friends? Just walk up to her?



There is no right way

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The honest answer is there is no right thing to do. No one knows what another person will say or do. What you can’t do though, is simply let your fear hold you back from taking the leap of faith and opening yourself up to her. Sure, she might say no, which is her discretion. It’s pretty much guaranteed though, that if you just stand back and do nothing you will regret it for the rest of your life.

To start, you shouldn’t just go up and lay it on her that you’ve been in love with her forever and you desperately want to be with her.  That is a bit much to lay on someone and might even scare her a little bit.  The most important thing is to just be honest with her. Start small, like asking her out on a date not as friends but as a couple. Try flirting more and don’t hide away from her by pretending you don’t like her.

You have to let her know you like her or you’ll be forever stuck in the friend zone, the terrible place where relationships never grow and nothing ever changes. You should have the courage to tell her directly because it’s going to mean a whole lot more if it comes straight from you.

You can make it happen

If you want anything to happen, you have to make it happen. You can’t sit around and make excuses and hope that one day she just falls in your lap. The world seldom works that way outside of Hollywood.

If you get up the courage to ask her and she says no, then at least you can take pride in the fact that you owned up to how you felt and actually made that first step. Keep in mind though, that a “no” now may not be forever. As time passes, she might actually change her mind and decide you’re not such a bad guy to go out with after all.

Hearing a “no” is better than hearing nothing at all because you never made that first step. Don’t let your fear control you, work past it and change that dream into reality. As scary as hearing a “no” might be, just think of how amazingly fantastic hearing a “yes” would be! Don’t focus on the negative, work towards the positive.

Just think that if you’re friends, you probably know her better than most of the guys she has or will date.  You have an edge in knowing many of the things she likes and dislikes already which is valuable knowledge when it comes to dating.  There will never be the perfect time to ask, so just go for the gusto and make it happen. When all is said and done, you’ll look back and be glad you went for it no matter the outcome.

"The Little Black Book of Sex Positions"

by Dan & Jennifer
(Now Available on Amazon!)

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