Tough situation but ....
Does the kid even want the car? He sells it and gets the real price after you gave a big discount.
If it was me, I'd just tell him you can't sell the car, but would be happy to go car shopping with him.

I would not consummate the deal for all the many reasons stated above.

The parameters changed and you are under no obligation at all.

I sold my pristine Supra that I bought new in '83 to a friend for his son in the late 90s (largely because his dad lusted after it) for much less than it was worth (felt like I was doing a good deed). The paint was good and the interior perfect. Everything worked and it ran great. It was perfectly stock. I told them it was an old car and it was "as is." After about a week, I kept hearing about things breaking as came across the car in a parking lot. The fancy factory stereo was gone and a cheap unit installed. The door handle on one side was missing. It looked terrible. About a week later, the son blew the engine (even though those were bulletproof). My friend implied that I had sold them a lemon (I found out later the son was racing and missed a shift). Now, I don't sell to friends.

I would never do that again. Especially if the person buying it lived nearby and I saw the destruction of my prized car every now and then. My father-in-law tells the same story about a '67 Mustang he bought new that the new owner promptly destroyed, so it is apparently not an isolated instance.

I once sold a '65 Mustang through a dealer. I had owned the car for a very long time and meticulously restored it. I rebuilt the engine and transmission and did the paint and bodywork myself. The buyer turned out to be a teen who found my name in the paperwork and called me about a week later. He was excited about his purchase and related to me all the "improvements" he was making (and had already taken a jigsaw to it to make it his own). He burned up the clutch in about two days and it needed another one. Made me feel sick.

If you have strong feelings about this car, don't necessarily think anyone else will feel the same or treat it like you did.

I completely agree with this and I also agree with those that wouldn’t put any kid anywhere near a bug. They aren’t safe, in the world we live in and a 16 year old kid is going to wreck whatever he drives. Usually, with his friends in there with him.

I had a bug, many years ago, and I wouldn’t drive a mile in one now.

Have a chat with the guy and explain your thinking. You were doing the right thing originally but he changed the deal.

^^^ That right there is the answer. The grandson will have more appreciation for the car because he put some work into it and learned something about the car.

I once bought back two cars that I sold in the past, because I didn’t like how the new buyers were treating them. Both were flawless, premium examples of their type when I sold them.

Had to spend a fair amount of money to undo the damage.

Some people just suck.

More times than not a kid's first car gets trashed or wrecked. If you want to help them find a car for the grandkid, that sounds like a good option.

This.

Was selling my VR4.

Kid came by with his dad and wanted to buy it.

1st car.

I said no.

Dad was a little shocked at first and said "really?"

Yup, too much car for a 16 yr old.

"But he's an A student"

Yeah, maybe, but that doesn't change the car and the fact he is an inexperienced teenager.

He went straight to full price, no haggling, thinking that would do it.

Nope, not selling it to him, sorry,

Someone had to be the realistic adult and that thing as his first car was a bad idea.

I did as well. I drove cross country four times in my 1966 Beetle.

Not today, Sports Fans.

I sold my 356 mainly because I just felt under-powered, invisible and a bit like I'd be buried in the thing if I got in modern traffic.

I get the appeal but even as a weekender I had to by hyper vigilant.

To the OP, helping your friend find a suitable car does indeed sound like the right thing to do.

When one of my dear friends sold me his 1996 LC over three years ago, he knew two things: I would take care of it and I would never ***** about the car, ever.

Years ago I was hanging out at MC dealer waiting on a tire change and wandering around the showroom. A young guy came in and wanted to buy the used 'busa they had there. The sales man asked him how long he'd been riding and the kid said this would be his first bike. The salesman said "sorry son I won't sell this to you. You'll die". The kid pitched a fit and the manager came out and said something like "anyone who pizzes and moans like you just did shouldn't be on anything more than a moped. Have a nice day kid".

So true. When my Dad passed away seven years ago I inherited his 1992 RX-7. Both my kids wanted it.

Nope, too much car.

I sold it to OneWhippedPuppy.

In the OPs case, it is a question of too little car:cool:

Yeah, that last line of the first paragraph does state that he wanted to drive it to/from work, and now he wants it for something different, so he changed the terms. I think you can back out comfortably.

Still, it could be that his plans changed because his situation has changed so radically. And you could still give the guy a lot of joy. So it's up to you what you want to do.

I agree, that the kid's probably going to thrash/wreck the car, and that's if he even wants it. Some kids would love a classic like that and some kids would hate it.

Years ago (~1990), my parents bought a 74 bug convertible that had been 90% restored, new top, new paint, new wheels, new interior, new stereo, etc... A guy had been fixing it up for his daughter. Turns out she didn't want old, she wanted something like a rabbit convertible, so the guy sold it.

That's a great story. Good to hear that those folks were human instead of just out for a buck no matter what.

Watch this and then ask yourself if you want to get into a crash in a car that was built with ‘50s technology:

https://m.youtube.com/watch?v=C_r5UJrxcck

And that Chevy has three times more steel than the VW.

I also realized that the old '74 911 (from my high school years) was my dream, not my daughter's. She liked posing for photos in front of it, not driving it. A nice little SUV (like my wife's 4Runner) was the bomb in my daughter's high school. I bought the wife a new car and kept the old 911 for myself. It was just a $5K car back then and I would never have bought one today, so it worked out well (got me started with Porsches).

My kids are 2 for 2 in this. Started with an Audi A4 and Mazda 3. Both gone.

Now they are both in Land Rover Disco 2, that are as big as anything on the road here and pretty under powered. It seems to have slowed them down and now they are seen by other drivers. Plus Mom told them no mas, do it again and you are walking.

you are not obligated to sell it.

does the kid even want it

I count myself very lucky in that the worst case for my kids was when my daughter backed our Odyssey van out of the driveway and into a neighbors car which was parked across the street in what was not considered a parking space and was usually empty. I paid them $500 and they got it fixed themselves (for a lot less I'd imagine) but no insurance company involvement on either parties part. I figured I came out way ahead on that as it only cost me a tail light for the van and some touch up paint.
We have friends whose daughter was given a brand new car by her grandmother upon graduating from HS. That car was totaled within a year do to inattentive driving.
The last Honda I sold privately I really had to learn about letting go. I got full price for it so no problem there. I saw the car a couple years later carrying a bale of hay in the trunk. Paint was thrashed and the headliner was sagging. It was perfect when I sold it as it had always been garaged and cleaned on a regular basis. I was proud of it. The kid whose dad bought it for her not so much.
I would have no problem not selling the car in the OP. It may sound hard hearted but you owe this 'friend' nothing. What about your kids? I'd keep it for them if they want it. If not, use it to fund something they do want, just make sure they put some sweat equity into it so they will take 'ownership' more seriously.

I agree with those saying he's changed the deal, also that its not the right first car for his grandson.

Perhaps offer to 'rent/loan' it to him, and let him drive to and from work for an agreed upon period. I did that with friend that had stage IV, just told him outright that in all due respect that the $'s would be better served elsewhere. He never got charged for the enjoyment he got from driving the old 911S.