☆.A.
I'd probably get to know the dad & kid a little better--then let him go.
My son's O. friends' dad often takes his son & my son places. He's also 8 and they have been for quite awhile.
On a side note: I have been amazed at the parents we DON'T know who allow us to pick up their kid, take him somewhere, & bring him back without knowing us hardly at all! We often will invite a buddy along, since my son is an only and some activities just scream :NEED A BUDDY! LOL