There is no such thing as a stupid question. Except that there totally is. With regard to some things, if you have to ask, you already know the answer.

Am I committing tax evasion?

Yes, yes you are. Stop trying to hide funds in overseas accounts. Stop “forgetting” to report earned income. Someone will find out, and you’ll be in way more trouble than if you had just checked the damn box to begin with.

Should I have that fourth slice of pizza?

No you shouldn’t, but that isn’t going to stop you. Just like you know that you’ll wake up feeling like a beached whale, swear that it will never happen again, and do it at the very next opportunity. Let’s stop pretending that we have self restraint.

Is this milk bad?

Yes. The expiration date has passed, and it smells more like something you’d clean your bathroom with than something you’d actually consume. Throw that sucker away and go pick up a new bottle.

Should I study this weekend, or head to my buddy’s bachelor party?

You’ve got that big test on Monday, but that’s ages away. Rationalize all you want, but you know you’re going to the party. The hungover shell of a human who shows up to take the test is going to regret it. As long as you go into it with open eyes, you’ll save time pretending and won’t be surprised by your failing grade.

Am I actually into to this person?

If you have to double check with yourself, you’re not. Maybe you’ve been dating for a few weeks, and finally realize it’s out of convenience. Or maybe you’ve had a few too many cocktails at the bar and are pretty sure you’re talking to a real-life model. Move along.

How old is too old to still be living with my parents?

Whatever age you are when you’re asking this question, there’s your answer. Time to find another job and get your own place. It makes cooking breakfast for the person you picked up the night before a lot less awkward.

My car is making a weird noise; should I get it looked at?

Of course you should, but you can also roll the windows down and blast the radio until you can’t hear it. If you don’t “notice” the problem, it doesn’t exist. Laws of physics, right?

Do I really need a retirement account?

Yes, but you really need that new outfit more. Go on, splurge now and look fabulous for one night. It’ll be worth it when you’re begging your kids to take you in because you’re too broke to even buy a new sweat suit.

How important is car insurance, really?

Very important. Go ahead, just see what happens if you get into an uninsured motorist accident with a BMW or Rolls Royce. It’ll make that annual premium look like a drop in the bucket compared to the debt you’re about to put yourself in.

Is that drink free?

We all know there’s no such thing as a free drink. If it’s sitting on the bar, it’s either just been ordered by somebody else (who paid for it, and therefore expects to drink it as well), or has some drug cocktail already slipped in (in which case, you should probably avoid it). Or the person who bought it for you has expectations that you really don’t intend to meet. Either cough up the dough and buy your own, or befriend the bartender so they’ll hook it up.

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