When it comes to cars and girls (or guys), most of us can think of one that got away. The car you should have bought because it would have made that final year of college so much more fun, or made you a fortune because they’ve since exploded in value and you’ll never be able to afford one again.

Maybe you didn’t buy it because you genuinely couldn’t scrape the money together. When you’re young and broke, finding the extra cash you need to buy something great, like a Nissan GT-R, instead of something serviceable but forgettable like a Nissan Versa, probably isn’t easy.

But how many of us can think of times when we could have bought something seriously cool, and had the money to do it, but when it came down to the crunch, we just didn’t have the balls? I’m guessing I’m not the only one.

Here’s an example. Back in 2007 I bought a 1980s Porsche 911 Carrera 3.2 when they were right at the bottom of the depreciation curve. I spent a few months looking for the best one within my budget and took a loan out to cover the entire purchase price. My son had just been born so there was zero spare cash swilling around to cover any costs beyond basic servicing. If it broke I was screwed.

Related: Would You Pay $20k For The World’s Rustiest (And Engine-less) Ferrari?

Credit: Chris Chilton

Which is one of the reasons I went for the 911. It might have been a brave choice compared to the modern used hot hatch I could have picked instead, but it was a pussy’s choice next to the Ferrari 308 GT4 or V12-powered 400 I could have bought for the same money at the time, and which I secretly coveted.

When it came to it I just wasn’t brave enough to risk buying an old Ferrari with the knowledge that I didn’t have any budget to fix it if it went wrong. And nor did I have the balls to buy a slice of Detroit muscle, something I’d wanted since I was a kid, because I thought it might take ages to move on in the UK and I’d have to deal with nutcase buyers when I eventually needed to sell. And since I was navigating the uncharted waters of new fatherhood, that could have been next week for all I knew.

Now both the Yankee V8 stuff and Ferraris are far more expensive, making purchasing them a much bigger commitment, if not entirely impossible. But maybe it was for the best. I quite enjoyed the 911, nothing broke, and I didn’t lose any money when I sold it, though the same woman I sold it to still has it and it’s now worth nearly four times as much, which kind of stings. But part of me wishes I’d just let heart kick head’s ass and bought the 400 or Dino.

When Sensible Pays Off

On the flip side of that I can think of occasions when life would have been a whole lot simpler if I had just been sensible. Like the dog of a Mk2 Golf GTI 16v I bought when I should have spent the same money on a tidy 8-valver, but was swayed by the extra 20 hp, the bee-sting aerial and the little red badge. That car was three years of hell.

Which hasn’t stopped my daydreaming about a $20,000 Maserati V8 Coupe from the mid 2000s. Those things look like great value right now, and I’d definitely buy one if it wasn’t for the fear of reliability and expensive repairs.

So what car did you have the chance to buy, but bottled it? Leave a comment and let us know.