Sometimes we do silly things in the never-ending quest for — or cars plural in some of our cases. We end up buying cars we shouldn’t own and selling cars we should have kept.

So my question today is: What car do you regret selling?

For me, it’s probably the 2000 Jeep Cherokee Sport I had in high school, which I sold once I graduated. The problem with that Cherokee was that I bought it when I was interested in off-road capability more than long distance drivability. As , my XJ rode on oversized tires, with a lift and roof rack and oversized bumper and lots of other farkles which looked awesome, but did nothing for daily drivability.

It wasn’t an off-road beast at all, but it was further away to its stock siblings than I would have liked once I realized that I would be driving the thing on the highway much, much more than I would be off-roading.

So, I sold it and decided to get something a little smaller, something that would be cheaper to fill up (this was in the throes of the , back when buying gas was a Mad Max scene for a broke college freshman like me.) After selling the XJ, I bought two shitty BMWs back-to-back. You can bet I missed the reliability of the Jeep then.

But I ended up in my afterwards, and forgot all about the crappy Bimmers and the lifted Cherokee, which was never quite in its element on the highway. Unlike that Jetta, which ate up miles and did it cheaply, too.

Now, I’m trying but to daily drive a 24-year old BMW and I’m missing that Cherokee again. Because it was a very simple machine whose only crime was being altered by someone other than myself. I’m thinking now I probably should have just kept the Cherokee, with it’s bulletproof 4.0-liter inline six, which gave me zero issues during my ownership.

I could have simply removed the lift kit and put it back on its stock tires with their OEM five-spoke wheels — which, by-the-way, are actually a solid wheel for the boxy Cherokee. After that, I could have undone the other “tasteful” mods and just ran the thing as close to stock as possible.

I bet that inline six would still be kicking just fine, with a little bit of love and care, while it’s stablemate in the garage, my 318ti, could sit a spell as I tear through wire harnesses and/or replace worn rubber bits. Of course, the other problem the Cherokee had is that it was an automatic and, well, I do place a big premium on shifting my own gears.

Still, I wish I hadn’t sold that Cherokee and instead just turned it into a stock, comfortable and reliable machine. Especially considering that my regret is slowly morphing into a desire for something David Tracy would probably call a “holy grail” XJ: a two-door, manual . That kind of can’t be good for anyone. Shoulda kept that XJ, José. But how about you? What car do you most regret selling?