My boyfriend’s roommate, Charles, is kind of an asshole. And I love him. When I first started hanging around the house, Charles was away for the weekend, but Joe and his friends all told me the same thing: “He’s an asshole. You’ll love him”. I didn’t understand how that could be a real thing, but then I met him and understood instantly. I learn something new every single time I talk to him. Sometimes he shows me movies I never would have known existed, and sometimes he teaches me how to potentially murder someone with brass knuckles.

One night, Charles was watching me respond to your letters and floated the idea of him providing a temporary advice service via snail mail. The solution we came to is that he will be taking your questions and providing some (tough love) advice to you in a handwritten fashion.

Tell A Stranger Your Damn Business: Letters To Charles

I would like to preface this with the fact that Charles can be blunt, mean, and sarcastic. These are not letters to or from me, they are letters from him. They’reย not going to be covered in glitter, balloons, and positive encouragement. In fact, it might be the opposite. But it’s going to be hilarious. Something that doesn’t really get touched on here is my sick sense of humor, and I think this is a good introduction to it.

Treat this like you would an advice column in a magazine. You can ask him questions about your relationship, job, or hobbies. He’s up for questions on drugs, guns, and sexually transmitted diseases. Really anything is fair game.

c/o Uncustomary Art
PO Box 354
Linthicum Heights, MD 21090

Dear Charles,

I just found out the only thing that turns my boyfriend on is watching Shaquille O’Neal put on gold bond powder. Do you think I should play ball or leave him?


Shaq-ly Confused

You don’t have to use your real name, but please include your full return address so that he can respond to you.
You actually don’t even need to use a real problem. Let’s just get weird with this.
Yes, this is international. I am funding the postage.
I am not going to be proofreading these, and although I am facilitating this hilarious connection, the opinions of Charles in no way reflect Uncustomary Art’s views.
This is an experimental thing. Right now, we’re signed on for at least the lifespan of a brand new pen and we’ll see where it goes from there.
Feel free to e-mail me photos of the letters you receive from Charles. That’s really the only way I’m going to see them. And I may compile a post of them in the future to share with those of you not brave enough to submit your own letter.
Get ready to be offended.

Questions? Comment below!