A few weeks ago, we here at MotorTrend revealed the sometimes ridiculous, sometimes unusual cars we drove in high school—or didn’t, as some of us took the bus or subway. Some of those vehicles we miss, but like most cars teenagers own, good riddance to the rest. After high school we naturally went on to acquire better cars, some of which, through lack of funds, interest, or enjoyment, we ended up casting off. But errors are great teachers, and most of these cars that got away taught us lessons about cars, ourselves, or both that later proved useful. It’s also just fun to see the past tastes (and mistaken purchases) of the staff. Enjoy this list of cars we wish we hadn’t sold.

2001 Audi TT Roadster

I owned a TT Roadster for a few years and eventually traded it for a Ducati Monster because the TT’s check-engine light would come on every time you looked at the dash. Well, it wasn’t exactly that often, but the codes were mostly emissions-related and expensive to resolve. Despite the hassles, the Roadster was a blast to drive and mine packed a 1.8-liter inline-four good for 180 horsepower. I still miss it; my next one will be a Quattro all-wheel-drive version with baseball-glove leather seats and 225 horses. —Ed Tahaney

1984 Volvo 245 Diesel Wagon

Youth is a time to experiment and to fail. That’s what ultimately ended up happening with my fourth car, a 1984 Volvo 245 diesel wagon affectionately (and a bit ironically) called Swedish Thunder. In the mid-2000s, homebrew biodiesel was all the rage, which pushed diesel-powered Mercedes models out of my price range—but put an overlooked, lesser-known car on my radar. I didn’t know anything about diesels, but I did know a thing or two about old Volvos. What could go wrong?

A lot, it turns out. I finally found a white Volvo with an overdrive manual. Its rarity and stunning outward condition blinded me to any lurking mechanical issues. I took one test drive and noted no flaws aside from the lack of power from its Volkswagen-sourced 2.4-liter non-turbo diesel inline-six rated for 81 horsepower and 103 lb-ft of torque. The seller agreed to knock a couple hundred bucks off the price to forego a prepurchase inspection. We shook on it and I puttered home at 65 mph, spewing smoke the whole way.

I would later learn that smoke wasn’t exactly normal—it was actually caused by shockingly low compression in all cylinders. Determined to make lemonade out of this lemon, I found a a lower-mileage Volvo 760 Diesel with the slightly more powerful D24T turbodiesel I-6 sitting in a pull-it-yourself junkyard. After pulling the engine and tracking down the extremely rare parts needed for the conversion…it just sat there. For four years.

I lost hope—and interest. Parked on the street, it was an eyesore. Realizing I’d never get to finishing the job, I sold the car for $700, and eventually all the parts I’d acquired as well. I gave up before even really trying, and looking back 10 years later that’s what I regret most.

Was it all in vain? Not in the slightest. I learned a ton about diagnosis and gained a better understanding of how engines work. Would I like the chance to finish what I started all those years ago? Someday, but first I have a never-ending BMW E30 project to finish. —Alex Nishimoto

1995 Mazda MX-5 Miata

A months-long search for my first sports car took me more than 1,000 miles from my East Coast home, down to Atlanta to drop every dollar I had on a 1995 Miata in Montego Blue over tan with a color-matched factory hardtop. I taught myself how to heel-and-toe downshift in that car, hustling along all 318 corners of the Tail of the Dragon. It introduced me to approachable limit handling. It was everything I love about cars.

I had the car prepped for a cross-country journey to start my gig at MT; I sorted the mechanicals, fitted new tires, added a trunk rack, the whole shebang. I was so ready to take my dear friend to the storied driving roads of Los Angeles. And then, during my first stop in Brooklyn, I street-parked my beloved outside a friend’s apartment and it was totaled by a drunk driver in the middle of the night and I suppose I technically “sold” it to the insurance company. I miss it dearly to this day. —Duncan Brady

1987 Porsche 911 Carrera

It had 120,000 miles, the Venetian Blue paint on the frunk was chipping, the Linen leather was graying from age, the A/C blew as cold as a panting Weimaraner, and the No. 8 main bearing was toast. But the prior owner had kept dutiful receipts for the past 50K, so I took a flyer on this amazing 930-edition with the bulletproof G50 transmission. (Note: Technically, this was my wife Lisa’s car, as she’s a driving badass who occasionally let me borrow the keys.) For three glorious years, we dusted Southern California foothill roads, joyously experiencing the raspy snarl of the air-cooled 3.2-liter boxer engine. Did we swing out the rear-end on hairpins? Hell, yes. Then, a relocation to Germany loomed. We had to sell the car. We moved. The economy collapsed. Five months later, we had to move back to L.A. again, with no 911 to salve our wounds. We had bought the 911 for $16,000 and sold it for $18,500. Not bad, until you realize good-shape 930 G50s go for triple that amount today. Crushing. —Mark Rechtin

1990 Honda Prelude Si

So many people who write about cars own, or have owned, Mazda Miatas. Count me in: I had a 1996 for about six years. And while I miss it, I think by the time I’d sold it I’d extracted about all the enjoyment out of it I could. But the car I truly regret selling was the car I replaced the Miata with: a 1990 Honda Prelude Si—not a four-wheel-steering model, but minty clean and with just 112K miles.

The Prelude hit the mood I was in perfectly—the ultimate evolution of everything that was truly great about 1980s cars, baked into a single wedge-shaped highway missile that handled. Retro-futuristic touches abounded—pop-up headlights, ultra-clean instruments, chunky binnacle buttons on the super-low instrument cowl, an elegant three-spoke steering wheel, even the diagonal pattern on the seats. I could go on and on. It was a car I just liked being in. I’d sit in it for a bit after parking it, lingering and taking in the whole interior vibe. It wasn’t quick or powerful, but it used its 140 horsepower authoritatively and the cable-operated shifter was absolute Honda perfection. Just a few weeks after buying it in Washington, it was on a trailer with my stuff headed to Michigan.

Once there, it felt too nice for Michigan roads or winters. It’d kill me to see it get beaten up and rusted out—so I stored it for a winter, then realized my anxiety about watching it deteriorate before my eyes wasn’t going to change. I sold it, and that was exactly what I needed then. It funded new vehicular adventures that made more sense for where I was in life. But now that I’m back in Washington, with smoother roads and no salt, it really feels like the right car at the wrong time. —Alex Kierstein

1995 Mazda MX-5 Miata

This probably isn’t the first Miata on this list, nor the last. [Actually, it is the last, but not the first!—Ed. ] Look, the Mazda roadster’s popularity—even beyond this publication’s office walls—is the predictable nadir of its outsize personality and minuscule price tag. I found my 1995 example on Craigslist in 2013 listed for $4,200. That was a steal, as it lacked rust despite being a lifelong Michigan car, and had only 73,000 miles. I threw on a crappy set of new off-brand tires, changed the oil, the differential fluid, and the transmission fluid, and maybe swapped the air filter. It was pretty much the bulk of my necessary upkeep.

That car needed nothing. It would sit most of the time, given Michigan’s sliver of annual Miata-friendly weather and my rotation of test vehicles, but it always fired right up, happy as ever to blat around the Detroit area. My use of the car waned even further when I moved to a new apartment that lacked a garage, forcing the Mazda into off-site storage.

Eventually, a colleague at my then job convinced me to sell it to him—he needed something in Los Angeles that wasn’t a 993 Porsche to keep miles off his 993 Porsche—and I haven’t stopped wanting the Miata back since it was loaded on the transporter in Michigan. Subsequent old-German-car ownership only made the pangs of regrets sting that much more. Fun cars are more fun when they’re reliable. —Alexander Stoklosa

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