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## 556: What’s the difference between “can’t” and “I’m scared, don’t wanna?”

Dear Captain Awkward, I’m a 25-year-old living at home with my parents; I received a BA in English/Creative Writing about two years ago, and I haven’t done much of anything since then. I’ve been struggling with depression and anxiety (especially social anxiety) for practically my whole life, and a couple months ago I was also […]

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#541: What kind of financial “help” do I “owe” my uncle?

My feet are cold, but my heart is warm thanks to the generosity of the Winter Pledge Drive contributors. Thank you so much! Support the site if you can! Today’s letter is about money and family and when those things come together in a manipulative and possibly sinister way. Dear Captain Awkward, My parents passed […]

#449: I hate my job, I’m broke, my commute sucks, and I maybe want to be a writer.

Hi Captain! My main question is: how do I keep going? I have 99 problems, I need to fix at least 95 of them but right now I can’t even seem to fix 1 so I am stuck. I’ve been actively job-hunting for over a year now. I know others have it worse, either through […]

#309 & #310: The Broken Record

Dear Captain Awkward, I need a second opinion. I’m at my wits end as to how to address something that has become a large problem with my boyfriend. My friends are no, help; I’ve gotten lucky, landed a good, caring boy, how could I have problems, lalalala-I-can’t-hear-you. I’m glad they approve of him, since I […]

#295: When failure moves into your house to stay.

Hello, readers. It is Day 2 of the Captain Awkward Dot Com half-yearly pledge drive. If you like it here and can spare a dollar, consider making a small donation and getting a copy of my short movie, The Wardrobe. Thanks to everyone who has contributed so far! Dear Captain Awkward, I have written to […]

#292: Wealth (& massive insecurity) is messing up my love life.

Hello Captain Awkward, I have an issue that you probably don’t get every day. I have a problem with wealth and dating. I’m in my late 20′s, and I have had the good fortune of becoming quite wealthy. Unfortunately, I am having trouble finding women who like me for me and not my wealth. Back […]

#252: How can I help my boyfriend when he won’t ask for help?

Howdy, Captain. I am in a four-year relationship with a lovely man. We’ve weathered serious storms and worked through what could have been relationship-wrecking issues, thanks to being forgiving, talkative, and evolving people. We’re easy-going, share humor and interests, and enjoy spending time together, and we’ve lived together for three years now. For about the […]

#238: If I tell my parents I am an atheist, they will disown me (or worse).

Dear Captain Awkward: I’ve been a closet atheist for almost five years, and it’s getting kind of stuffy in here. Here’s some background: I’m a Dawoodi Bohra Muslim, which is sort of like the Muslim equivalent of the Catholic Church, only smaller. We have organized clergy, a pope-like figure, etc, etc. My parents are devout. […]

Question 161: “Please fix my life?”

Dear Captain Awkward, Hello! I hope all is well with you and things. I have a long rambling question that is either summed up as “money: how do I get it” or “life: how do I fix it,” so, yeah. Relevant life history: Recovering alcoholic dry drunk unintentionally emotionally abusive father, unintentionally emotionally abuse mother, […]

Reader question #110: How do I claw my way out of this depressing living situation?

Dear Cap’n Awkward, I’m stuck in a depressing living situation and I don’t see a way out. I spent much of 2010 living on my own, doing a halfway-decent job of getting by, occasionally needing my mom to help me with rent like many a financially irresponsible 22-year-old. The thing is, I’ve been pretty badly […]


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