Mailbag: My Sister Is Sleeping With My Friends, And I Think She’s Hot

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The Mailbag is back with a brand new invention. Grabs a hold of me tightly, flow like a harpoon daily and nightly. Will it ever stop? Yo, I don’t know. Frankly, I hope it never stops, and if I keep finding gold like this in my inbox, it never will. Anyway, it returns this week with a situation I’ve never really put much thought into, but one I know some of you can relate to. The emailer, Tim (probably not his real name), faces a quandary of collegiate relations and brotherhood, with just a tinge of incest.

“Tim” attends college in Florida with his older sister. “Angela,” as he calls her, is close with his fraternity brothers–really close with a few of them, if you know what I mean (you do). Tim doesn’t quite know what to think of it all for a couple reasons, one of which is mildly disturbing. His email is below.

Sup Dorno,

I guess I’m supposed to start off by saying fuck you or whatever, so fuck you. Your hair is pretty nice but overhyped in my opinion. Just thought I’d share that.

Anyway, this is about my sister. First off, I go to a prominent school in the state of Florida (not Miami), and I’m in a frat (obviously). Enough about me. My sister (let’s call her Angela) is in the top sorority at my school. She’s a year older than me and one of the reasons I chose this school. We’re pretty close. I’m in the top fraternity. My fraternity hangs out with hers a lot, we get matched up a lot for all the events, we tailgate together, etc.

I wouldn’t say my sister gets around too much, but she definitely has had some hookups that I know about, and they’re pretty much all with guys from my chapter. Here’s where you come in. I need advice. Half of me feels angry with my brothers for hooking up with Angela. Isn’t there an unwritten rule about banging your brother’s sister?

Then the other half of me like yeah, I get it, and I’ll be honest here since this is anonymous…I think my sister is hot. I’d call her a solid 9.5 on a sober scale. She’s tall, long brown hair, tan, athletic build, green eyes. I feel weird typing that out, but honestly Dorno it’s the truth. You’d wife her up in a heart beat.

I have two questions.

1. Should I be mad at my brothers for hooking up with her?
2. Is it normal to think your sister is attractive?

Fuck you sincerely,


First of all, this sentence only works in the context of a fraternity, or else we’re talking about a whole different level of fucked up: “Isn’t there an unwritten rule about banging your brother’s sister?” In real-world context, yeah, there’s a rule against that.

Now to Tim’s first question. Yeah, Tim, I think it’s fair to be angry with your fraternity brothers for having sexual intercourse with your sister. You know what that means, right? It means they’re sticking their privates inside hers for sexual gratification. That’s your big sister, Tim! Your flesh and blood! The daughter of your parents!

In fact, your friends actually expect you to be mad at them and are most likely shocked that they haven’t yet faced any repercussions from it. Sex with your friend’s hot sister is on every straight guy’s dream to-do list, because A) she’s hot, but also because B) it’s wrong, and wrong is hot.

Furthermore, I think rule 1A of the Brother Guide commands that you do everything within your power to prevent your friends from sleeping with your sister, and rule 1B states that you better get mad as hell if they do manage to sleep with her. It’s your duty. That shit shouldn’t fly, especially without having to answer to you. Sack up, Tim.

Now for question two–which is the reason we’re all here. There is a monumental difference between the adjectives “pretty” and “hot,” and it breaks down like this: “pretty” is how you describe a girl who you can’t or shouldn’t publicly state that you’d like to have sex with. Moms can be pretty. Your girlfriend’s friends can be pretty. Your girlfriend’s sister can be pretty. Your aunt can be pretty. All these people have something in common: sleeping with them is off limits. Guess who else can be pretty, Tim? I’m sorry to say that your sister can be pretty.

Your sister cannot, however, be hot, because you want to bang a girl you describe as “hot.” Tim, I’m just going to say what we’re all thinking. You want to fuck your sister.

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Dillon Cheverere

Dillon Cheverere (@DCheverere) is the Vice President of Media for Grandex, Inc. Email:

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