Your friend eh? Everyone is telling ypu to let this go. But here are some suggestions.

Test driving a car is free, and depending on how much someone drives and the difference in MPG, it might justify monthly payments or outright purchasing another vehicle. Also, Sometimes old cars cost about the same to insure as newer ones.

Renting a TV for a week is pretty cheap. Walmart has good deals on TVs that just a few years back would have cost a small fortune.

Most mobile carriers will give you a deal on a new phone or even a free phone or a biannual credit toward a new phone with their service. Plus, both Samsung and Apple have admitted to slowing down service to older phones to encourage new purchases.

Buy the dude a set of sunglasses.

Take the old sunglasses apart and put the pieces in the appropriate recycling containers. Take the old phone and tv to the appropriate recycling plant. He can donate the car and probably get a better tax write off than trading it in, plus it would help someone out. Getting rid of the old things in a reasonable manner might help justify and ease the weariness of a new purchase.