What is the right age for teen boys to date? [I Need Dating Advice]

If they are friends already, what is the difference between dating and hanging out for them? What exactly is being forbidden that they wouldn't just be able to do otherwise behind your back.

I think this is a scenario where you speak with him and set expectations and reaffirm responsibilities. Talk to him about how things might turn out if they don't work out. About what jealousy can do. And just generally inform him about how reality works. And then let him.

You are going to end up in a much better place if you can serve as a trusted guide and mentor than you will if you are the person he has to hide his life from.