Haven't owned a vintage car since shortly after I first got my motorcycle license (1976), but my first car was a 1937 Buick Special 2-door sedan that I had for about a decade. Showed it at all the local vintage antique shows (of which there were a lot, as western Pennsylvania is a real hotbed of antique cars), and later realized that the Indian I currently own was at most of the same shows - that was two owners earlier.
Now for the fun part: What most of you guys are talking about, to me, aren't vintage cars. They're life.
My father was a Chevrolet dealer, 1950-1965. I virtually grew up in the dealership. Was down there every Tuesday afternoon, after piano lessons. My teacher lived across the street from the dealership. My earliest memory as a child was father coming home on afternoon for lunch, summer of 1953, driving this white roadster with red interior. Yep, a '53 Corvette - years later he told me it was something like #14 off the production line. Gave me a ride during lunch (this was a habit of his during the next 12 years) and took it back to the shop.
I found the car again, twenty years later. Six blocks from the family home. Sitting outdoors, alongside the residence's garage, rotting away. I spent the next two years trying to buy the car from the elderly lady who lived there but she wouldn't sell - it was her late son's car, he was killed in a '58 he also bought from dad. The car eventually rotted away to nothing and I lost track of what happened to the remains.
Back then, I loved summer. Dad made sure he came home every day in whatever was the strangest car that was sitting on the lot at the time, and I got to ride in stuff as diverse as a Humber Snipe, Hillman Minx, Renault Dauphine (the first car I ever drove - age 12), DeSoto Firedome, various Packards and Studebakers, etc., etc., etc.
However, I've never ridden in another Corvette. Never figured out why.