Asking Someone for a Date - It seems simple enough, but it can be the most difficult part of a date

So what do you do?

Biggest clue: THINK AHEAD

You don't want to be standing there going, "Um, ah." when the object of your affection says "Yes."
You can't just looked stunned and be too shocked to utter the next sentence.
You can't wait for that very moment to try to think of what on earth you can do on a date.
You need a more impressive beginning.
If you're at the start of a relationship or asking for a first date, take the pressure off by not using the "D" word.
Don't ask for a "Date" and don't call it a "Date."
If you're uncomfortable saying, "Would you like to go out with me."
Then don't say it.
Make it casual.
But (just a reminder)THINK AHEAD.
Make it specific.

First - two deadly questions NOT to ask:
 Do not ask, "You want to go out?" it's too open-ended and can lead to awkward follow up conversation.
 Do not ask, "What are you doing Friday night?"
It's too vague. It may leave your potential date wondering exactly what you have in mind.
The other person doesn't know if you're just curious about what she/he is doing on Friday night or if you want to do something with them...
Try something along the lines of:

"You like to rollerblade? I was thinking of going out to the lake on Saturday. It's great out there. Would you like to go with me?" 

Or if you're really uncertain or uncomfortable about getting together - go with a group. Ask the question:

"Hey, there're a bunch of us going bowling on Saturday. Would you like to go?"

The operative word here is "us." It immediately takes the pressure off.

Planning activities to do on your date and getting together in a group are good ways to go - especially if you think you or your date might get "tongue-tied."
If you're busy or there are a bunch of other people in the conversation, you won't hit awkward silences and won't have to talk all the time if you don't know your date very well.

In summary, just remember when you are asking someone out:
1) Plan ahead
Know what you are going to say AND what you want to suggest to do on the date.
2) Be specific
The other person will be much more comfortable if they know exactly what your intentions are and what you want to do.

AND try to relax and enjoy yourself - worst case - they'll say they can't go out and you'll find someone else who will. Someone who appreciates you.
In other words, if the person you are asking out doesn't have enough insight to recognize what a terrific person you are, then they're just not too bright now, are they?