Whether a date’s spontaneous or planned, the first or the last date, or you’re young or old, sooner or later, going out with someone comes to this: Somebody has to ask for the date. No matter how much or how little you plan (and regardless of your reputation, your Aunt Sylvia, the knot in your stomach, the advice of your friends, your New Year’s resolution, or your success with dating or lack thereof) nobody, with the possible exception of Adam, ever made a date without asking for it.

Setting Up the Date

I bet that even with God as the go-between, sooner or later Eve expected Adam to pony up and find the courage to ask if they could take a walk in Paradise, and if he didn’t, well, it explains a lot about the snake, don’t you think? Face it, the only thing scarier than the first date is asking for the first date.

But if you can remember that you’re not looking for a cure for cancer, that you won’t die even if he or she says “yes,” and that life as we know it will continue no matter what your potential date’s response, you may relax enough to actually (gulp) ask for a date.

Do or dare: Making the approach

Gazillions of perfectly normal (and lots of less than normal) people have all gotten nervous about asking for a date. You and I and everybody else are connected to a long line of sweating, nervous, stuttering, tongue-tied souls, and even the slick ones feel anxious on the inside about asking for a date.

Do you feel better? No? Well, I was afraid of that. Never fear — in this chapter, I tell you some things that should comfort you in the asking, help you in the consummation, and protect you from any possible devastation beyond a teensy pinch on the ego.

Risking 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.

A brush-off with style

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.

Just when you think a compliment’s safe

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.