Don Tuite wrote:

Jay, don't over-analyze. Go ahead, but let the kid know he can bail
(and come back) without a big scene. Some days it will seem like a
good idea; some days it won't.

That's the best advice. If a young teen thinks you're keen to have him
do something, he'll probably attempt to "lose interest" and note your
reaction. Offer to him, support him, make the invitations, and don't
be crazed if he doesn't take an interest. He'll change his mind or
not.

Then, if you like, as he gets closer to solo age and to whatever
you'll consider appropriate one-on-one-dating age, offer it to him
again and see what he does. :-)

Rob