Ask Anyone on a Date over the Phone

Do you want to ask someone out, but didn't have the guts to do it in person? This is how you ask out a boy/girl/significant other over the phone!

Steps

Check that the person you're calling does not already have a boyfriend/girlfriend. Skip this step if the person you are calling is your boyfriend/girlfriend.
Know what you are saying. More often than not, a person will call another without knowing what to say.If you are unprepared, then you could create an awkward silence. Avoid this by writing out what you're going to say and rehearsing. (See Tips.) Still act natural though!
Be specific. Asking a person out without knowing where to go will hurt you when the day comes and make you less confident. If it is a movie or a concert then mention the time as well.
Act Casual. Start up a conversation first. Once you feel comfortable talking to the person, go ahead and start with your rehearsed conversation.
Avoid the dreaded Recover From an Awkward Silence. If there is a silence longer than fifteen seconds *Don't count, of course*, then say "It's OK if you don't want to..." or "You don't have to tell me now."
Accept rejection. If the person on the other side says no, but does want to go out with you some other time, try again! Tell the person that you understand. Don't get angry, rude or sullen.
Say "Thank you" if he/she does say yes. Congratulations! You have just asked a person out over the phone.

If you want to go to a movie or concert, than make sure you have enough money for the tickets.
Sound confident. If you sound shy, then he/she will probably feel that you're not ready for a date.
Make sure no one is around for your big question. Don't be anywhere near your parents or anyone that will nag you until you tell them who you just asked out. This also improves your confidence.
There are also cheap or free things to do on a date. School dances or going to the beach or a lake for a picnic is always good.
Asking a person out over the phone is probably the best idea for a shy person and asking for a date over IM/Email is probably not a good idea, because then you'll only see text. In person or over the phone is the best bet and it is more polite.
If you want to go to a restaurant than ask the person what kind of food they like or ask them if they like Italian food because most people do.

If you're rejected, don't let up, but also loosen up a little. They may not like you, but they may be doubtful about their feelings about you.