If a friend can serve as an intermediary and determine if your boy of choice is also into you, take advantage of this invaluable opportunity.  If it is still ambiguous as to whether he likes you, then you need to be direct in your approach; no frills.  Decide if you will ask him in person, by phone or e-mail, or as we did back in my day, by the paper note.  Again, you could have a friend ask him on your behalf, but it is usually not a choice method. 

Choose Your Words

I cannot stress this enough: be casual.  Even if your heart is pounding loudly and you are shaking so badly that you believe you will cry, you need to exude confidence throughout.  I recommend using humour whenever you can.  For example, promise to pick him up in a jalopy similar to the one in Archie Comics and help him tie his bow tie.  By keeping things light, you will be perceived as fun.  Also, be candid yet tactful.  Telling him that you think he’s cool and the two of you would have a fabulous time together is flattering.  However, telling them that you would like to marry him, have his three children (two girls and a boy) and move to Bali with him where you will walk hand-in-hand together on the beach under the stars is crazy.

Accept the Prospect of Rejection 

Now, I think we all know that this story has two possible endings: either he says yes or he says no.  If he says yes, have a great time!  However, if he says no, don’t be terribly disappointed or over-analytical of the situation.  All you can do is accept it, move on and possibly try again.  He has reasons for saying no and they may be honourable or not.  It’s not your problem to figure him out.   

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sadie hawkins, eat your heart out!

Remember though, the odds are in your favour as long as you’ve formulated a solid plan.  Men are as nervous, if not more, about asking women out as we are about asking men out.  It can be a welcome and flattering change for a guy to be asked out by a woman.  So you go, girl! 

Just don’t do the Macarena on the dance floor.