As long as everyone else is doing it, why not.
1993: 1966 Galaxie 500. Identical to this car, save for hubcaps. My dad, who was into old Fords and had several while I was growing up, bought it when I was 15, it was the first car I regularly drove (not legally mine):
Fun car with loud exhaust, thirsty 390 which got 10 mpg or so no matter the speed. It tangled with a minivan one fall day, got it back after insurance as a project, but dad decided it was too much work. Sold to a local hobbyist who was going to fix it, never saw it again.
Then on to a 1985 Tempo GLX. Not really “mine” per se, but I drove it a lot, and felt a connection. I also maintained it for years. This car belonged to my mom, who kept it for many years, and later was used by kids and family members. I drove it for a bit after the Galaxie and before the next car. This was a fancy Tempo, with nearly every option, it was like this but a pleasing medium blue color (I remember the name: Medium Regatta Blue Metallic) with matching interior:
I drove this thing hard, and it never really complained. The car stayed in the family until 1999, when mom finally declared it surplus, and let it go, with 190K on the clock. I think she bonded with it, and was sad to see it go. Engine and transmission never needed mechanical work, but the primitive engine computers were quirky in later years, and it seemed to eat mufflers.
1995-present: 1964 Mercedes-Benz 220SE. 18 year old me just happened to be on an errand (probably in the Tempo), and saw a neat old car I had seen around town, parked in a local lot. It happened to have a “for sale” sign in the window. The rest is history (pic is from many years ago, before I could get wide whites for the car):
I’ve had many good times in the car - drove it through all my school years, hauled friends, 4 guys worth of hockey gear, all my worldly possessions, drove though snow/ice storms without complaint, and even used it as a DD for a while after graduation. It has needed work now and then, but has generally been reliable, and is enough of a sentimental object to want to keep forever.
2002-2005: 1989 Mercedes-Benz 300SE. I was gainfully employed, was thinking it was time to retire the old dear from DD duty, and had always wanted a W126. I wasn’t into assuming too much debt or buying new. This one owner car in a perfect color came up for sale locally, so I went for it:
It always posed well with the fintail:
The car had but a couple minor hiccups during my tenure, but was getting miled up, and as I was still young, I wanted something faster. At nearly 200K on the clock, I sold it to an older guy who’s W126 recently was hit, and he wanted a good replacement. I hope it is still out there.
2005-2006: 1998 Mercedes-Benz C43 AMG:
I had always liked these, and they depreciated to my level. I found a nice one owner car with 50K on it, and took the plunge. I liked the somewhat go-kart (compared to a W126) feel of it, but the ride was rough and rear seat space comical. I started itching for something else, and a weird engine tick at around 65K miles sent me looking again.
2006-2013: 2002 Mercedes-Benz E55 AMG:
I found a nice 25K mile tectite grey W210 E55 - a fairly rare car. I bought an aftermarket warranty, which paid for itself - the car had a few hiccups, but nothing that stranded me. I really liked this car and thought of keeping it forever, but storage space simply won’t allow that, and the running costs for this car could be aggravating. I decided to cut the cord and let it go, but I still have sellers remorse now and then.
2013- 2014: 2013 Mercedes-Benz E350 Bluetec:
First new car. Short term lease on an unwanted car. Got a good deal on it, liked it but didn’t fall in love like I thought I would. Still a good experience, people liked this car, I got many compliments.
Late 2014-2016: 2014 Mercedes-Benz E350:
Another sweetheart lease deal on a leftover car. Decently optioned, nice colors, smooth car, but not emotional. A pleasant driver.
2016-present: 2016 Mercedes-Benz E250 Bluetec 4Matic:
Yet another sweetheart lease on an unwanted car. W213s were already arriving, dieselgate had people scared, they wanted this thing out of there, and were willing to deal hard. I also like this one more than my prior 212s - the powertrain is great, optioned almost exactly how I would built it (just doesn’t have drivers assist and I would probably prefer luxury trim and a lighter blue). Lease end is on the horizon, not sure if I will buy it out or move on, but I have enjoyed the feel and economy of the car.