The email address of the question inbox you seek is at the end of the post. Please read the instructions first!

1. The blog wouldn’t exist without you, so, thanks!
2. Submitting a question gives me the right to publish it on the site and use it in other media (a Captain Awkward book, for example) in perpetuity.
3. We can edit questions for content and length, but usually don’t. If you want to keep the people & situations in your letter anonymous (and you probably do), change the names & details before you submit. Please also try to keep your text under 400 words.
4. We’ve been at this a while, so, try searching the archives to see if your question has been answered before.
5. Please also familiarize yourself with the site policies.
6. I don’t share email addresses, real names, or personal details of Letter Writers with anyone, ever. However, harassment or violent threats will be documented and, if necessary, reported to law enforcement.
7. Questions aren’t answered in any particular order or on any schedule. I don’t answer all the questions I receive, and I can’t promise private answers.
8. Re: Point #7: This is not a crisis hotline. If you are in a scary or violent situation, if you’ve been assaulted, if you or someone you know is having suicidal thoughts, please call a trained person who can give you the immediate assistance you deserve. Here are some lists of helplines that others have compiled. I haven’t tested all the links & numbers for accuracy, so please know that you can also type “helpline” + “[nature of your crisis/issue/problem]” + [where you live] into a search engine and come up with results local to you.
9. New! Improved! It’s really helpful when Letter Writers include their pronouns (and the pronouns of the players in the situation) Reasons: I don’t want to misgender people. When sexism and gender politics are a factor in what’s happening in the letter, it helps me figure that out much quicker. When we cut down on 50-100 “but we don’t know what gender people are” comments, it helps me moderate comments much quicker.
10. New! Improved! Pronouns = great! Kindly steer clear of intended-to-be-inclusive blanket terms like “women and femmes” and acronyms like AMAB/AFAB, which may be useful in context on discussions hosted by other sites but are being frequently hijacked by “gender critical” (i.e. transphobic/TERF) “feminists” to argue that the assumptions made about someone’s gender as a baby must follow them around for life (and define their rights and inclusion in certain spaces). If you think how someone’s gender is perceived is affecting a current situation, find another way to say this, even if it’s clunky. Thank you!
11. New! Improved! The more descriptive you can be in your email subject line, the easier it is for me to get to your question. “Question…” “Question for Captain Awkward…” = I have thousands of these, all of them no doubt GREAT and IMPORTANT questions, but it’s hard to latch onto a particular one. “Help with emotional baggage that is packed in literal boxes” = Makes it easier for my brain to say “Hello, what are you?”
12. New! Improved! I do my best with data security (using two-step authentication, for example), but you might consider using a throwaway or anonymous email address when sending sensitive questions or information.
13. New! Improved! Are you a woman, married to or dating a man, and you are writing for help about a situation that primarily affects him (his relationship with his family of origin, his workplace conflicts, a conflict he’s having with his social life, his mental or physical health, his difficulty in setting boundaries with others)? There are lots of letters that cover this in the archives, going forward please strongly consider asking the gentleman in question to write to me himself, since outsourcing this kind of emotional care-taking and fixing to you is maybe part of the problem.

Thanks again for reading. The email address for the question box is awkwardmailbox@gmail.com.