Hmm, as a guy, honestly it can be an embarrassing situation for him, but if he likes you he will have to suck it up. And if he has a car and can drive, you should have him take you on the date. At least until you get serious enough that he is comfortable with you driving him.
It is very okay to ask a guy out and take him on a date. This will prove how much you are committed into knowing him better. It will also be a sign of confidence and boldness, which guys find attractive.