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…
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#449: I hate my job, I’m broke, my commute sucks, and I maybe want to be a writer.
Tagged with: employment, Job hunting, Job Search, Writing
Posted in Mental Health, Money, Reader Questions, Work, writing
Posted in Mental Health, Money, Reader Questions, Work, writing
#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…
Tagged with: anger, break up now, breaking up, Dating, divorce, grudges, hoarding, judgement, love, Relationships, Sex, wits end
Posted in Dating, manipulation, Mental Health, Money, Reader Questions, Relationships
Posted in Dating, manipulation, Mental Health, Money, Reader Questions, Relationships
#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.…
#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…
Tagged with: Dating, fairy tales, insecurity, Relationships, trust, wealth
Posted in Dating, manipulation, Manners, Mental Health, Money, Overthinking It, Reader Questions, Stockholm Syndrome
Posted in Dating, manipulation, Manners, Mental Health, Money, Overthinking It, Reader Questions, Stockholm Syndrome
#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…
Tagged with: depression, halping, helping, mental health, Relationships, unemployment
Posted in Mental Health, Money, Overthinking It, Reader Questions, Relationships
Posted in Mental Health, Money, Overthinking It, Reader Questions, Relationships
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.…
Tagged with: bad decisions, consequences, crime, despair, downward spiral, poverty
Posted in Families, Mental Health, Money, Reader Questions
Posted in Families, Mental Health, Money, Reader Questions
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…
Tagged with: depression, ithaka, making a fresh start, overcoming depression
Posted in Families, Mental Health, Money, Parents, Reader Questions, Work
Posted in Families, Mental Health, Money, Parents, Reader Questions, Work
Reader question #108: Jealousy and Law School
Dear Captain Awkward, My boyfriend and I have both just started law school in different cities, and I’m having trouble adjusting to the change in our financial situations. For the last couple years we have been living together, making roughly…
Tagged with: competitiveness in a relationship, jealousy, law school
Posted in Dating, Money, Reader Questions, Relationships
Posted in Dating, Money, Reader Questions, Relationships
Reader question #46: I have a great job and a great life, but I feel like I should be doing more to help others.
Dear Captain Awkward: I’m a 23-year-old in Chicago who’s had a pretty smooth transition out of school and into a job I like. I get to use some of my skills from my history major, I have flexibility and can…
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