The red line: your not good with you're grammar

Mar 19, 2014

Dear Freelance Editor,

I’m a freelancer who works from home. Recently, I decided to try online dating - I need to escape my comfortable home office/burrow. Immediately after I created my profile, some guy wrote me a message saying, “Hello. Your [sic] so pretty!” I immediately slammed my laptop shut and have been tucked in a fetal curl under the bed ever since, panicky and depressed about my romantic prospects.

Was I wrong to reject him just because he cannot distinguish between your and you’re? He was kinda cute, and there are a lot of dust bunnies down here.


I Don’t Want to Die Alone, Albeit with Impeccable Grammar (IDWTDAAWIG)


Oh, how I feel your pain. As a freelance editor, the your vs. you’re mix-up generates countless hours of proofreading angst, and nothing makes me do a Liz-Lemon-style-eyeroll faster.

I will also confess that back when I was dating, I was the Correct Usage Ice Queen. My long-suffering Significant Other still has to meticulously spell check every text he sends me.

So, I totally understand your response!

But it is probably unfriendly (and quite close-minded) to run screaming; nobody is perfect all the time, be they client or dating prospect. Next time, perhaps do not summarily reject this fellow.

Instead, send him this link, containing a very straightforward and easy-to-follow guide:


When to use you’re:

You’re is a contraction of you are. Sound out the sentence you are writing. Can you expand you’re into you are in this sentence?

If your answer is “Gee, lady – no, I cannot do that”, then PLEASE DO NOT USE YOU’RE. This is an iron-clad and very simple rule.


1.) You’re so pretty, Internet dating prospect!

Can we translate that into “you are so pretty”? Yes. Then we’re good to go, and I’m so flattered – I HAVE been trying to get more sleep, thank you for noticing!

2.) You’re a terrible snot, you know.

I really am, but that usage is correct.

When to use your

Use your EVERY TIME that you cannot expand it into you are.

This is because your is a possessive adjective, but let’s not worry about labels. Back to the examples:


1.) Sirrah, I am afraid that your initial grammatical error is turning me off.

Expanding that into “‘you are’ initial grammatical error” does not make any sense. Thus, this usage is correct.

2.) Please take a moment to consult this handy-dandy guide; it is not too late to mend your ways.

It is NEVER TOO LATE, friend!

Crawl out from under your bed, open your laptop, and see if that comely young man is willing to adjust his grammatical habits.

Do it before the dust bunnies become sentient – because then your [sic] in real trouble.

This has been a message from a Freelance Editor.

Have a question for our resident Red Liner and mender of grammar-challenged hearts, Kate Hamill? Email her at, or leave it in the comments!