Her name was Jenny. She was a fire truck red, 1997 Jeep Cherokee complete with a powerful 4 liter engine, a tall boxy frame, multiple broken windows, a dented fender, a self destruct button (not a joke), and all the best memories of my childhood. She was the absolute best car I could have ever hoped for and last year I had to trade her in.

If you’re like me, your first car is a part of you. Like an over worn favorite shirt, people know you by it. I was the red Jeep guy.

But all great things must come to an end and that end looked like handing over the keys to Jenny (and a small piece of my heart) to acquire a trusty, reliable, utterly boring 2009 Silver Honda Civic. Ok, so I’m still a little torn up about it.

Buying a car is a stamp of adulthood that most people don’t experience until they’re out on their own—in the real world. And kind of like getting an apartment or making friends after college, it’s something that few of us twenty somethings are really prepared for.


Step 1: Take a Good Long Look at your Finances

The first step I took in my car buying process was figuring out how much car I could reasonably afford. Let’s be honest, most of us millennials aren’t sitting on fat stacks of cash that allow us to throw a ton of money at a car payment and also that’s probably not very smart. So before you go falling in love with a Range Rover, maybe run a few calculations to see what that monthly bill will look like.

Pro Tip: If you’re reading this, you probably can’t afford a Range Rover.

Even though all I wanted in the world was to replace Jenny (my Jeep) with a brand new Jeep Grand Cherokee (whom I would probably have named Yenny, or Penny, or Lenny) it just wasn’t in the cards for my wife and I because new Jeeps are expensive.

Good questions to ask yourself here:

  • What could I/we reasonably afford as a monthly payment?
  • What’s my current car’s value? (Kelley Blue Book is a pretty reliable source for this info)
  • How much money (if any) can I contribute to a down payment?
  • How’s my credit? (this matters because you may need a co-signer)

Step 2: Figure Out What Matters to You

For instance, I bought my boring Civic because it’s a fuel-efficient, reliable, reasonably affordable car that will probably run until the Zombie apocalypse. That’s all well and good, but I realized about 3 months after purchasing it that I just really don’t like small cars. First world problems, I know.

There were several other small SUVs in the same price range that we could have gotten, but I got in a rush to buy so I just kind of did it. Side note: my wife gets frustrated with my propensity to just do things so this would be a good example of that.

Ok so this part is important and honestly I wish I would’ve done a much better job at remembering this throughout the process. Buying a car is a big commitment. Ideally, you’re going to have this thing for several years and it’s not the sort of thing you want buyer’s remorse on after a few months.

Some things that could matter to your decision making:

  • Do I/we have a long work commute or travel a lot?
  • Do I/we have a dog? Will we spontaneously get one in 5 months making me further regret buying a small car?
  • Do I/we have kids? Will we in the next 5ish years?

Step 3: Research Cars

Like any other big purchase decision, car buying takes some research (shocker I know). You need to figure out what you want, what you can afford, and what’s out there. If you get really lucky, all three of those criteria may line up and you get your dream car. Haha, just kidding–you’re in your twenties. Forget about that dream car.

When I started car searching last year the main tools I used were Kelly Blue Book and Carmax, but I’ve since discovered several other tools which I’ll list at the bottom of the article. I would suggest checking out all of these tools and seeing which ones are most helpful for you.

I spent the majority of my time on CarMax’s website because 1) they have good pictures, 2) they sell used cars which is what I was interested in, and 3) it was the first car-buying site I came across. I do recommend using their website to learn what is out there, but the general consensus of what I gathered is that their prices are higher than you can find at other dealers. That said, they also only sell higher quality cars. Again, do your research.

The primary criteria I judged cars by were:

  1. Price
  2. Mileage
  3. Year
  4. Brand
  5. Driver Reviews
  6. Auxiliary Input
  7. Cruise Control (my wife’s car doesn’t have it)
  8. Color
  9. Cool Factor

Step 4: Go Talk to Some People

I’ll be honest here, the more you read the better off you’ll be. I’ve got nothing against used car salesmen, but I dealt with about 4 or 5 and every one of them disagreed with what the others had said. Their goal is to get you in a car—that’s it.

Going to a used car lot is about as fun as judging a black licorice competition (you’re welcome for that mental image), but for most of us millennials, without the cash to buy a car straight up off Craigslist, it’s probably something we’ll do in our life. Or you could just one of those new fangled websites to buy cars on—links below.

What I’m saying is that most likely you will eventually you have to get out of your bubble and go to a place with cars. Then you have to talk to people about cars like you know what you’re talking about. So do your research as best as possible and if you know someone who knows cars, take them with you. Which reminds me…

Step 5: Remember Car Buying is a Negotiation

I don’t know about you, but I don’t have much experience playing hardball. So when it came time for me to buy a car, I went to the place, gave them my car and some money, and walked away with a used one. There’s nothing wrong with this, except for the fact that I could probably have gotten them to lower the price some. If not, I at least could have tried. What’s the worst thing that could have happened? They say no. That’s it, that’s literally the worst thing. This is a lesson most twenty somethings probably need help with.

At one point in the car buying process, I actually had the dealership lift up my Civic on a hydraulic lift so I could look at the underneath part of the car. Who knows what the hell I thought I was looking for.

In hindsight, I would have left that day and come back the next so I’d have time to clear my head and the dealership would think I wasn’t interested. I guess my tip here is to do just that. Early in our car searching process, one salesman offered a leather seats upgrade when he found out we were about to walk out the door. We didn’t end up buying that car, but I still wonder what could have happened had we tried to negotiate for the Civic we ended up purchasing.

Also if you’re blessed with a friend or relative who thrives on negotiations, take them with you. I have one such friend and it probably costed me thousand of dollars by not having him there.


If I had to summarize all my car buying thoughts and opinions it would basically boil down to this:

  • Know your numbers (monthly payments, down payment, etc.)
  • Do the research (what kind of car you prefer, best cars in your price bracket)
  • Talk to trustworthy people (ask friends, family, reliable Twitter followers)

First Time Car Buyer Resources