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Archive | November 2011

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Question #144: I am tempted to get a makeover so I can ask out my crush.

Captain my Captain, I’m twenty years old, I’m in my third year of college and for the first time I have a fat – no – a phat crush on someone. I’m not new to dating or youknowwhat (well, not extremely new anyways..) but I’ve never felt so hopelessly into someone before. I guess you […]

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Question 143: I lent an ear to a friend, how do I get it back?

Dear Captain Awkward, I want to be a good friend and a good listener, I really do. I have a lovely, kind friend who I have known for a long time. She has some mental health issues. She is going through a very rough time and I totally want to be there for her. The […]

Question 142: Did I offend my date when I accepted his offer to get me drinks? (Drinks 101)

Dear Captain Awkward, I’ve really no idea how to sensibly start this story. I’m in my early twenties and I’ve never had a boyfriend before. In fact no one has ever been interested in me. And then I met this guy. We met on a drunken night out and while nothing but holding hands and […]

Question 141. Breakup second thoughts: Can these pants be fixed?

Dear Captain, This is a question about tailoring ill-fitting pants. So there’s this lady in my life. She’s a fantastic lady. I met her last summer and we connected pretty much instantly. I was coming off some serious heartbreak, she was coming off some other drama. So we took things slowly, but we started to […]


Thanks for being the best group of readers a girl could ask for. And thanks to the letter writers – we really don’t do this without brave people who share their stories. Here’s the poem of the day: Postcard from the Party You have to be invited, and there’s nothing you can do to be […]

Guest post! “I don’t have a Friend Zone.” (Question 140)

Today, the awesome regular commenter known as “k”has been promoted to Ensign Perception in the Army of Awkward. She will help this letter writer explore the universe of people he would like to sleep with. Dear Captain Awkward, I have a problem when it comes to being attracted to people. I suppose colloquially this problem would be […]

Question #139: How do I deal with my “cheap, cowardly” friend?

Dear Captain Awkward, My friend is driving me crazy. We’re going to call him Dan. Dan is in his mid-twenties, has graduated from university, and has been working a steady job in his field for two or three years now. He still lives with his parents completely free of charge. He’s generally a good person, […]

Question #138: How do I help my employee overcome his self-loathing?

Oh Captain my Captain, I am the manager of a retail establishment and recently had an eye-opening experience with one of my employees.  He is normally a smart, funny, articulate, motivated, an amazing artist and very thoughtful guy.  Twice now I have had bizarre experiences with him where, over the course of his shift,  he […]

Question #137: I got promoted at work, and now supervising my old friends (and lovers) is awkward.

Dear Captain Awkward: I recently got a promotion (yay!) and now people I have to supervise people I’ve previously worked alongside (less yay). There’s one employee in particular who’s had a problem with taking instructions from me. He and I were hired around the same time, and he has more experience in the field. I […]

A Plea

Guys, I love your detailed, nerdy hearts, I do! And I am one verbose lady! But I’ve got some letters in my inbox that are over 1500 words long. Those will never get answered, because I will never read all the way through them and I don’t have time to edit your thoughts and your […]


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