There’s nothing really complicated about asking for a date. Ideally, you should ask someone in person so that he or she won’t have any difficulty in “placing” you, but telephoning is perfectly acceptable, too.
It is best, however, to have gotten to know the person you are asking through previous conversation before suddenly springing a request for a date. Those conversations give you a chance to ascertain your compatibility with each other. If you call, mention the last conversation the two of you had together and how much you enjoyed it. You might also mention the setting and some of the topics you discussed to help jog the other’s memory. Then simply say something like, “I was wondering if you would like to go with me to the (movie, dance, etc.) on Saturday night?”
If you are worried about your mind going completely blank when you make the call, the authors of How to Date With Confidence, Barbara Siegel and Scott Siegel, recommend that you simply make a list of things you want to say before you call. Not a word-for-word speech, of course. Just a few words to jog your memory. (No one can see you looking at your notes on the phone!) If the other person should decline, don’t take it too personally. Perhaps they feel they don’t know you well enough. If this is the case, try to become better acquainted before you ask again.
In the event that the person you call declines, simply say something like, “Well, maybe another time.” and let it go at that. Don’t try to change the person’s mind. You will only make a nuisance of yourself. Besides, there is always another time. If someone you like calls you for a date, and you are available for the time requested, you have it made. But what if you aren’t available? Or, what if you aren’t interested in the person who called? What should you do then?
If you are interested but aren’t available, you should say something like. “Oh, I’m sorry. I promised I’d take my brother to band practice that night. Would you give me a rain check? Thus, you express your disappointment, tell the caller the reason you can’t make it for the date, and request to reschedule it for another time. The best thing to do is to suggest setting another date, time and event on the spot. If the caller says he or she will look for another event to take you to, but doesn’t get down to specifics at that moment, it’s a good idea to say how much you appreciated their call the next time you see them, and how much you regret having had to refuse. Chances are, they’ll think of you again.
But what if you really aren’t interested in going out with the person who calls? You want to turn the caller down gently, and yet you want to close the door to future calls as well.The best way to do this, say Barbara and Scott is to say something like “I’m kind of involved with somebody else right now” or “I’ve just gone back to my old boyfriend.” This way, the caller doesn’t see it as a rejection of him or her personally, but just that you happen to be committed to someone and unavailable to anyone else. Few people will take offence to this kind of a gentle turning-down.