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Archive | May 2012

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#261: I keep falling for fixer-uppers

Dear Captain Awkward, I hope you and your army of awesome readers can help me! I’m 28 and I find myself in the awkward position of getting divorced and simultaneously losing my best friend. Long story short, I was also dating my best friend and we broke up so she can go back to her Darth Vader Husband. I’m […]

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#260: Sense and Sensibility and Saying Stuff Out Loud

Dear Captain Awkward,   I’m afraid my question is a little on the vague and general side.   I feel like Jane Bennet, whose “feelings, though fervent, were little displayed.” I just don’t wear my heart on my sleeve, and for the most part I’m very happy to be that way. But I think it’s […]

#259: “I’m in love with someone who treats me badly.”

Hi Captain, I’m in a sucky situation. I’m in love with one of my friends and he doesn’t treat me very well – even as a friend.   I started seeing him very shortly after the end of a very long, serious relationship. I said “this has to be casual, don’t ask me what we […]

#258 = #191 + Bridesmaidery

This is a follow-up to this post: http://captainawkward.com/2012/02/15/191-annual-reminder-time-get-your-teeth-cleaned-get-your-eyesnaughty-bits-checked-and-stop-hanging-out-with-crappy-people/ Dear Captain Awkward: First of all, I want to thank you and your commenters SO MUCH for being such kick-ass human beings and providing so much support and insight into the situation when I was so blind to what was going on. If I could, I’d invite […]

#257: Does having my awesome career mean I have to lose all of my relationships?

Dear Captain Awkward, Here is my problem. I made a bunch of friends when I was in my 20s. Then, when I was 30, I went back to school to finish my BA, and because my GPA from my first round of college was so very low I told all my friends I was going […]

#256: Not feeling the whole dating thing right now.

Dear Captain Awkward, I have become convinced that I am turning into a cold, emotionless robot a la Britta-Bot if you’re into Community (<3) Anyways. I ended my last serious relationship about a year ago, and since then I’ve been on a few first dates with some pretty cool people (or so i thought?). These […]

#255: Breaking up with a client (and surviving the resulting guilt-trip).

In linkmania and internet fame news, Proffitt from Good Girls Gone Geek interviews me about this here site today. And now, a question. Hey Cap’, I’ve wound up in a rather unpleasant business arrangement, and I was hoping for some advice on disentangling myself from it. To summarize: For the past 2 years my sister […]

Linky Links of Linkyness

Lindy West reacts to a new book by the authors of The Rules with the correct amount of “What the everloving fuck?” (h/t Bitches Gotta Eat) “So, essentially (according to these jokers), online dating is a forum where you put yourself up for auction and then passively watch while men compete for your silent company […]

#254: Torn between two lovers!

Dear Captain Awkward: There’s no way I can think to say this without sounding like a brat, but here goes. I’m sleeping with a guy that’s completely in love with me and supports me in everything I do. We get along great, the sex is great, he’s someone I could see myself raising a family […]

#253: “This was not the FEELINGSART we were looking for.”

Dear Captain Awkward, I hope you can help me with coming up with a script for an awkward conversation that needs to happen. Here’s the situation: My husband and I (!!!) got married (!!) on Saturday. It was amazing in every way except for one—we made a guestbook for people to sign. The guestbook was […]


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