If you are considering letting someone drive it who does not have the same love, admiration, respect for it... you should stop yourself (and them) right there. Because if something were to happen, you would always feel that little twinge of blame.
I'm with you, Tammy. And, Patrick-I agree with what you have to say. Fortunately, I am blessed with a lovely wife who shares my passion for fun vehicles-including motorcycles and trucks.

Heck, I gave her an '86 Z-28 Camaro (350, 5-speed, posi) for Valentine's Day. This, so she wouldn't put a lot of miles on her '98 Silverado Z-71

Plus, it bought me some time having to finish HER '67 GTO...
I have let my wife drive my 'Vette. She loved it-especially doing 90 MPH over Lookout Pass in Montana. She has driven it herself once-to get some key copies made. I would let her drive anything I own-she is good at it, conscientious and more careful than I am.
The only other person I have let drive my vehicles is my father-I wanted him to experience the Corvette thrill as well. He is also very careful-I offered him to "stretch her legs" and he still only went 70. But he was right there next to me when we used a GPS to calibrate the speedo in my '70 Chevelle 383 wagon (along with Mom and wife) when we rocked that puppy all the way to 100 MPH. Again, this is Montana, daylight, familiar roads, no drinking. I'm not stupid.... BTW, the wagon's got the full Hotchkiss suspension upgrade (F/R) and awesome SSBC brakes.
That said, I am generally not comfortable letting others drive my vehicles. I know what I have, what it needs, the brakes, steering, etc. Others are not familiar, and may not "get" the fact that some of my cars don't have power steering, power brakes, have 4-wheel drum brakes, etc. People I know, and I know their skills-perhaps. It definitely will depend on the vehicle.
Reading your post, Denise, his background, his brothers and his "buddies"-I have to say NO, sorry-get your own toy.
Rick