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Why Guys Don’t Ask

Editor’s Note: The following is an excerpt from the book The Art of Rejection: Because Dating’s Not a Science. It’s an Art (Revell) by Hayley and Michael DiMarco.


Before we get to dealing with the end of relationships, let’s chat about the effect the fear of rejection can have on us way before the relationship even starts. If you read Marriable, you know all about our chapters entitled “Stand Up and Be a Man” and “Nice Guys Really Do Finish Last.” The next page in our analysis of man-habits is his fear of rejection. This is the kind of fear that can hold a guy back from even asking a girl out on a date in the first place. As we see it, two types of fear keep guys from making a move: the fear of being rejected and the fear of rejecting others.

The fear of being rejected keeps scores of men on the dating sidelines, frustrating anxious and impatient women everywhere. Because of a guy’s mythical mental belief that a girl saying “no thanks” will do irreparable harm to his psyche, nice guys are going dateless all across the land.

Paralyzed by fear, many times the nice guy will just opt to “settle” for the aggressive or persistent girl that asks him out, regardless of compatibility, because then he doesn’t have to deal with the risk of rejection. But what happens is that the guy essentially becomes “trapped” in a badly matched relationship.

Double the trouble: When the fearful nice guy is combined with the “just friends” girl, the problem only doubles. He really likes her, and she’s more than happy to hang out with him—she just doesn’t like him “that way.” Of course, because he never asks her out, he never gives her the opportunity to tell him he has no chance. So they have their own little “don’t ask, don’t tell” policy, all the while wasting time and stringing out emotions.

The first step in reducing the risk of rejection is learning how to flirt. Check out The Art of the First Date and Marriable for a crash course in doing the pre-dating dance. The overarching answer to why guys should start risking rejection and start asking is in this taste from Marriable:

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If you still are afraid of the chase, then consider this. What if we were to give you an endless supply of $1 bills with which you could buy lottery tickets at no risk to you? And say we guaranteed that in your lifetime, one of those dollars would hit the jackpot. Wouldn’t you be laying those greenbacks down in a heartbeat, knowing your time was going to come? Trust us, we’re not encouraging gambling or settling your retirement account with lotto tickets, but really, that’s the type of control you have over your dating life. You have an endless supply of date invitations to offer—all you have to do is spend them. So get our there and start asking. It’s the only manly thing to do.

Rejection is a part of life. When you live your life in fear of rejection, you look weak. And weakness isn’t attractive. Learning the art of rejection is hot. It shows you’re confident enough to ask for what you want, and you’re not afraid of a little two-letter word.

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