A few weeks ago, I sold the one constant thing in my life for the past four years. While it was a hard decision to make, it was the right thing to do if I was every going to preserve my truly southern Jeep while living in upstate New York. Its now vacant parking space has left me with a set of juxtaposed emotions that would leave any gearhead spinning – what do I buy next?

My old 1999 Jeep Cherokee XJ Ruby. This was her “fuck you” side.

Even before I sold the Jeep to live and frolic in the land of the free and the home of the salt-less winters, I was shopping for its temporary replacement. You see, unbeknownst to the Jeep’s current owner, I have full intentions of owning Ruby again… eventually. In the meantime, why not try something else? Sure, New York winters are more salt than snow, the used car market is terrible, and most everything is filled with rust, but it can’t be that hard, can it?

“…has typical NY rust… $6,000 or best offer…”

Turns out, it can. Unlike normal people, I’m plagued with pretentious standards when it comes to cars. I can’t buy anything new – it goes against my morals. I can’t buy anything inherently reliable, and I’d rather walk than drive anything built within the last decade. To top it off, I’m a little girl when it comes to rust. Even still, every rust-free, “like clock-work” car I’ve owned, I’ve ended up selling. I’m even actively trying to sell my “needs-nothing” Subaru despite it being a great on-paper candidate for what I want out of a car. Too bad on-paper and real life don’t hold hands together.

So utilitarian, you’ll think you’re driving a Jeep.

When I bought the car, I knew I was taking a big risk. Having previously owned an automatic, six cylinder Subaru, I ultimately sold that car out of boredom. Despite knowing this, I was getting ready to sell the ideal commuter car – a 2000 Honda Civic DX with a manual transmission, manual door locks, manual windows, AND working air conditioning – to buy another version of a car I already determined to be boring. But, a Civic doesn’t have 250 horsepower, all-wheel drive, and enough cargo space it should be classified as a van. Despite its many desirable attributes, my current Outback is still not what I want.

An engine like silk, a transmission like valium – reliable and smooth valium, but valium nonetheless.

What I want is what I had. Hunting for cars is always just a game of tracking down the ones that left a burn mark in your psyche – the ones that taught you more about engineering than the classes you wish you would have taken; the ones that saved your life; the ones that thrilled you; and the ones that helped you grow into the person you are today. When doing this exercise, I can’t help but think, “you already had what you’re looking for. Why didn’t you just stop there?”

Battlewagon and Ruby – the red wagons of my dreams.

Unknown then, in May 2013, I owned the beginning of what is now the greatest fleet I can dream of today: a combination of a stock, low mileage, rust-free, 1999 four door Jeep Cherokee with the ideal factory setup – beefy four liter straight six, rugged manual transmission, and legitimate four wheel drive; AND a then-rust-free 1997 Subaru Outback that is to this day, my absolute favorite car I’ve ever owned. My chances of true automotive happiness will never be that in my favor again.

So what went wrong? Why instead of stopping there did I proceed to ruin the two vehicles I want right now?

The perfect daily driver – if it had 3.73 gears and selectable lockers.

All it needs is snow tires, a 4.44 six speed, a stripped interior and a roll cage.

I like to think it’s curiosity’s fault. One could say it’s because I can’t leave well enough alone, but I don’t think that’s true. I once owned the most ideal vehicle for 2017 and left it alone so much I sold it. Curiosity seems more to blame than anything else and despite hating myself a little for doing what I did, I’m glad I ended up letting it get the better of me. In the end, I over-abused, undernourished and dismantled my old Subaru only to then re-engineer (poorly I might add) a near-perfect specimen of an endangered species. Those actions taught me rather poignant but important life lessons about being a gearhead – the more you do to a vehicle, the more risk you take in eliminating the relationship you’ve built with it. Maybe it’s best to leave emotions out of the equation? Maybe you should never get attached in the first place? Then, you can be like everyone else and not care. Or, you can give curiosity a chance at ruining your life for the better. For me, I’ll keep hunting to feed that curiosity – even if it lands me on the side of the road.