This has been a problem for us over the years. Below is a partial list (I have some bad memory sectors). This has been a problem for us over the years. Neither of us had any self control with cars and often contemplated selling organs to purchase a new car.

Sadly, our self control has not improved in retirement, PLUS our organs are now worth much less.

High School / College Years
1953 Chevy (in 1963)
1955 Ford Fairlane
1956 Ford Fairlane
1958 Chevy Impala

Post college / Married (now includes wife’s cars owned at same time)
1966 442 Convertible (in 1970)
1970 Pinto
1968 Monte Carlo
1970 Monte Carlo
1973 Olds Cutlass
1974 Monte Carlo
1976 Monte Carlo
1979 Monte Carlo
1968 Toyota Corolla
1976 Datsun 280Z
1981 Monte Carlo
1980 Citation
1985 K-Car (lasted 2 months)
1986 Buick Electra
1993 Nissan Sentra Wagon
1995 Nissan Maxima
1998 Nissan Maxima
1999 Nissan Altima
2001 Nissan Maxima
2003 Nissan Altima
2004 Nissan Maxima
2007 Toyota Rav4
2009 Infiniti G37X AWD
2010 Nissan Murano SL AWD
2013 Acura RDX AWD (Great car, but I REALLY miss my G37)

1985 Chevy Celebrity Wagon - Briefly learned how to drive in this then took it as a hand me down
1980 Chevy Citation - Basically my first car, nothing special but was a great car
1986 Cavalier - Basic but fun car (wife's car)
1990 Nissan Pickup - Boring and gutless (wife's car)
1989 Chevy Beretta GTU - Most unreliable car ever but really fun to drive (V6 + stick)
1995 Ford Ranger - Had large tires but was gutless (wife's car)
1995 Nissan Ultima - Pretty average (wife's car)
1996 Chevy Cavalier - Very unspecial, worse mpg than my Z24! (wife's car)
1997 Chevy Cavalier Z24 - Very reliable car and great gas mileage (35+ HW mpg easy)
1999 Chrysler 300M - Still rocking this as "my car"
2001 VW Jetta VR6 - Disappointing reliability (wife's car)
2009 Mazda 5 - Disappointing gas mileage (wife's car) - Only brand new car we ever purchased
2009 Chevy Traverse LT - Drives really nice but gas mileage isn't great in the city (wife's car)

I think I deserve a new car for myself!

I don't think I have ever seen those words together in a sentence before.

It really was... I think the V6 model was the POS. Ours was the 2.5 liter 4 cylinder with a 4 speed manual. To this day I've never driven any 2WD car that comes close to what it could do in the snow. In no way was it sexy and it had the typical domestic interior flaws but the chassis was solid. Believe me as a high school teen I tested it's capabilities for taking a beating.

As a teen, I tested the ability of my Dodge Aries to go anywhere. It too was really impressive in it's abilities. I drove it back from Jacksonville Beach, FL to Western MD, in 11.5 hours. I don't know how fast I was going because the speedo only read up to 80. I literally held the accelerator to the floor for most of the trip. After I got back the alternator failed, the power steering pump started leaking, and the air con never worked again. The only belt-driven accessory that survived was the water pump.

Heck, even the RX-7 coupe was really amazing. I had a Jeep Wrangler swap ends in front of me in the snow. Not only did I keep the RX-7 pointed in the right direction, but I did it while swerving around the Jeep. I've taken the RX-8 out in the snow, but didn't push it too hard--it's too nice.

How long do you all KEEP your cars? Some of you have went through a lot of them! The next question is...have you ended up hating most of your cars or do you just get sick of them and want change? I've kept mine until they became too expensive to keep fixing.

1. 1988 Honda Prelude
2. 1999 Hyundai Tiburon (new)
3. 2010 Nissan Versa hatchback (new)

I ended up hating the first 2 cars. I bought them for the looks, and they were the only sporty cars I could afford at the time. The Honda was a rust bucket, and the Tiburon was loud in the interior and little things costing big money kept happening to it, so it was no longer worth keeping it. Now, that I'm older, I'm more practical too. I got an excellent deal on the Versa. Considering that it's a boring looking car, I love driving it WAY better than I ever liked driving the other two cars. The only thing I'm unhappy with the gas mileage. I drive mostly in the city, and Nissan rates it at 28 mpg. I'm consistently getting an average of 20 mpg. Granted, my driving habits aren't conservative, but I wouldn't expect to get that poor of gas mileage from this car.

This might make me feel old...
69 Impala 2 door. 327 engine that we took out of a wrecked school bus.
75 Chev Monza with a 305 V8 from a pickup. Went like stink if you could keep it pointed in a straight line. Terrible idea.
81 Challenger (like Tom's), but brown and white. I loved that car.
88 Mustang 5 liter, 5 speed. Excellent, but the hard ride got old pretty quickly, and NOT winter friendly
82 Dodge Omni for the winters.
90 (I think) Chrysler Daytona (wife's car)
86 Honda CRX (a blast)
90 Mazda pickup
89 Subaru wagon. Interesting: it didn't seem to have a model name.
90 Eagle Talon Tsi AWD. Loved that one too.
04 Subaru WRX wagon. Bought new and drove it for 9 happy years until last week.
07 Impreza (wife's car) leased
11 Forester (wife's car) leased, still in the garage
2012 Kia Optima Hybrid. So far, I'm very happy with this. Just one week... But I know I'll miss the WRX.

Thanks for the stroll down memory lane.

In general, we keep them until several months of repairs exceed what new car payments would be, but other factors also apply:

1977 Toyota SR5 P/U - later received a 231 V6 and TH350 trans - Became too unreliable.
1983 Honda Prelude - Can't haul a boat with it- +had >100k miles
1987 Ford Bronco - Hauled boat to Colorado River for many years - repairs got expensive after 175k miles

then I got married in '89 and Mrs Classic brought to the mix a ...
1979 FIat Strada - pumpkin orange... fuel supply issues made this one unreliable
1986 Nissan 200SX (hers) - >175k miles - would actually love to have one of these again
1993 Saturn SL1 (his) - kept this one 11 years and >190k miles - best and cheapest car I ever owned
1993 Saturn SW2 (hers) - this one had unresolved electrical issues that made driving unsafe - dealer "couldn't find problem.."
1996 Chevy Suburban (hers) - kept this one 12 years had >200k miles
1964 Rambler 770 Classic (project car - still sitting...) - did I mention still sitting?
2000 Cadillac Sedan DeVille (his - gift from great uncle) Flooded by Katrina
1978 Chevy El Camino (was my dads, gave to our oldest boy) Flooded by Katrina, but resurrected and kept on life support - currently replacing fuel pump with one in-tank to feed new fuel injection system.
2006 Chrysler 300C (his) - 115k miles and going strong - so far
2008 Chevy Suburban (hers) - 58k miles and just paid off!
2012 Fiat 500 POP - (My parents won it in a raffle and gave it to our middle boy who is only 15 1/2!) 500 miles and hopefully many more to come

Plymouth Horizon (year?) - purchased it for $150 shortly after getting my 365, and ran the hell outta it .
Wheelchair accessible bus (year?)
94' Dodge Caravan (owned since approximately 1999) modified to be wheelchair accessible