My oldest was about 14 or 15 when she went on her first date. The boy (who could not drive) came to the house, and they walked down the street to a cafe to have cake. I remember it was raining and they shared an umbrella. He paid. They returned to the house and hung out in the living room, while we all kept out of their hair.
The rules early on were pretty simple: she could either go on a group date, where we were doing the driving (such as a movie) or the young gentleman caller could come to our house to hang out. This is so I could keep an eye on them. Be prepared for your son's date to feel more comfortable if he goes to her house, rather than to your own. Parents of daughters are much more protective.
At 17 she has yet to be on a car date but around here kids get their licenses late, since we have lots of public transportation options. She is now able to go on dates that involve the bus, subway, etc. And we've loosened up about visiting her boyfriend's house - it's okay as long as his parents are home and we've confirmed that. She has a 9:00 curfew on school nights and 11:00 on weekends.
Youngest daughter is nearly 16 now, and has never gone on a date. She is interested in boys, but just not interested in dating any of them just yet. They kinda scare her, I guess!
Best advice I can give you is to recognize that kids develop at different rates, and some kids are, indeed, ready to date at 14 (my oldest) whereas others are later bloomers (my youngest). If your son is showing a genuine interest and you are sure it's not the influence of peers, he's ready, and he'll be fine.
I had my first boyfriend and "date" (not involving a car) at 13. By 15, I was going on car dates already. But, my parents knew the boy very well, because he was my brother's best friend.
