Buying Two New Cars While We Were Broke

I will always remember my first car in high school. It was a blue Plymouth Voyager van, handed down from my parents.

As long as I paid the gas and insurance, I was able to drive it wherever I needed.

That van saw plenty of great times and there was something very functional about it. Plenty of room for friends and to hang out when we didn’t want to go home yet.

As a high schooler, it gave me freedom that I had never had before, being able to drive myself around town while making sure to get home before curfew.

When that van finally died, I was able to borrow my an old Buick from my parents for a short period of time. While I was grateful to have those 4 wheels, driving a Buick as a high schooler wasn’t ideal.

My First Real Car Purchase

That prompted me to buy my first real car with my hard-earned cash. I went down to a local auto dealer where a certain car had caught my eye on the side of the road.

It was a 1999 black Jeep Cherokee and it was awesome.

It had 4×4 drive, power windows, AND the back windshield wiper actually worked. As a high school senior, I was in love.

And, for $5,000 cash, it was all mine.