Don't be afraid for a rejection

The First Rule to asking for a date is this: No guts, no glory. The worst-case scenario is that the prospective date says no. At that point, you’re no worse off than you are at this very moment.
Rejection is definitely not fun, but a rejection is only one person’s opinion of you. You don’t like everyone, and not everyone is going to like you. If someone says no, then he or she misses out on getting to know how truly terrific you are.
Rejection can be the beginning of opportunity. Scads of hugely successful people just wouldn’t take no for an answer. Think about Fred Astaire: When he first went to Hollywood, a talent scout wrote, “Big ears, too skinny, big nose, can dance a little.” Many famous beauties and stars in many fields had to cope with someone’s negative opinion of them — nobody hasn’t faced rejection. The question is: Are you going to let it get you down? Of course not! Alexander the Great probably conquered the world by the age of 30 because some shortsighted lass turned him down — maybe because he was too intense or short or something. Maybe that rejection made him want to make more than most Grecians earn. (It’s a pun; say it out loud — but definitely don’t use it until the fourth or fifth date or after you’re married or your last kid leaves for college or your hearing has gone.)
Rejection means that that person says no but not that everyone will. You need to realize when no is no, when someone’s showing absolutely no interest. If someone consistently says no when you ask for a date, it’s okay to say, “Look, I hear that you’re not interested, and I don’t want to be a pest. If you ever change your mind, here’s my number,” or “I’ll call you in a year,” but then for heaven’s sake, don’t call any sooner than that. With time, the sting really does go away.
Conversely, if you really don’t want to go out with someone, don’t say, “Maybe” or “Call me next week.” Just say, “Thank you for asking, but it’s just not possible.” Remember that the world is a very small place. You may change your mind, or that person you turn down may marry your best friend or be in a position to hire you someday. There is no reason to ever hurt someone whose only sin is being interested in you, so be gentle but firm. Rejection isn’t gender specific. It’s not any easier for guys to face rejection than it is for women. We’ve just programmed men for power, and asking someone out is boss, even if the whole experience is tinged with fear. Either sex can feel more powerful by taking the initiative and asking someone out. Biology has nothing to do with the ability to tolerate possible rejection. Women, if you’ve never asked a guy out, you should do it for your own liberal education. Guys love it. However, they may think you’re hotter to trot (sexually) than you really are, so take that into consideration.
If you’re afraid of rejection, you may miss out on a lot in this life, which is pretty darned short as it is. See if you can put that angst away, take the chip off your shoulder, and go for it.