Scarred, you have received some wonderful advice here. Your feelings sure bring back memories though. When I was asked out by someone (who I later married BTW) it felt really weird. I had been married in my teens and was divorced after nearly 25 years, so I had NO experience on the dating scene. It is a little scary, but if you take some precautions as others have mentioned, you will be just fine.
Try to think of this as a way to get to know someone better. You are not considering a lifetime commitment here. You also won't owe this man anything, so don't feel obligated to him for anything more than you really wish to do. You can do this, it just takes a little practice.
Relax and have fun! I guarantee it will get easier with each date.