Send Us Your Email Quandaries

Sometimes a teeny little mistake in your email can land you in seriously scalding water (see: that time you by accidentally sent that pic to your lady friend's mom). That's why I've teamed up with the new Outlook.com to give you some advice on how to handle your email conundrums.

So, here's how it will work: You send me your most frustrating, craziest, and walking-on-thin-iciest email issues (for instance: What time is the best time to email your boss when you're "sick"?) to etiquette@deadspin.com, and I'll answer my favorites in an upcoming column.

But, before I take your queries, let's get started with some basic tips. The following things should never, ever be in an email message by the time you hit "Send."

Quotes in Email Signatures

We get it: Life moves pretty fast. If you don't stop and look around once in a while, you could miss it. We also realize that the Dude always abides.

So maybe your high school yearbook only gave you a single line to express yourself, and a well-known classic rock quote was an efficient way to let the world know that you are a misunderstood snowflake. But emails are sent to bosses, loved ones, loved ones' parents, and people who may begin to question their decision to do business with you. And you never know: Maybe that person on the receiving end of your email absolutely hates Ferris Bueller's Day Off or The Big Lebowski.

Any Email Address That References Something Besides Your Name or Business

This includes references to boy bands ("1directionisntenough"), fictional characters ("lonelyholden"), or feats of strength ("benchpress350"). Seriously. Just declare your devotion with "really meaningful" tattoo or something.

Obvious Copy-and-Paste Jobs

There are tons of reasons why you'd want to copy and paste a message to a bunch of people. Maybe you're a PR flack sending blasts to journalists, or just somebody trying to make your mass-sent party invite feel a bit more personal. Either way, the secret to a good copy-and-paste job is that it doesn't feel like one. One surefire way of blowing your cover: If your message's font formatting shows the bulk of the message as one style, and the "Dear ____" greeting as another. Format that thing to be consistent, or appear amateur.

Comic Sans

Everybody knows that you close deals with Wingdings.

Of course, this is all novice stuff that you (hopefully) already know. So send in your harder questions to etiquette@deadspin.com, and then check out the new Outlook.com to start flexing your newly found skills.

Seth Porges is a New York-based writer, editor, on-air commentator, and entrepreneur.