Most men consider dating is something that they cannot do. But it's always not the same. Most of the shy men tend to take too much of pressure of making an effort when they are out for a date. And most of us do not even think that they could actually date a person as they do not know about the fact as to how it would go.
And by that we don't mean the girl, well of course you should, but if you are asking out a girl, go to a place which you are comfortable and familiar with. A familiar setting will help you be relaxed and more focused on her. Also make sure it is an informal setting so that you can be yourself.
Take conversation backups:
It is okay if you find yourself out of words or conversation ideas. That happens with most introvert people. So you can think of some nice conversation ideas and work on them beforehand. But don't make them like a speech. Take interest in all of them and make sure she is interested as well.
Drink a little:
We all know that drinking a little can make things more relaxed and more open. So go for a couple of drinks, and only as much as you can sincerely handle. Go for something light which will bring the best out of you.