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Archive | March 2012

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#218: My anxiety is messing up my relationship.

Dear Captain Awkward: I think I may have messed things up with my amazing boyfriend, and I just feel terrible about it. Let me preface by saying that I am 19 and he is 20, about to be 21, and we have been dating for just over 3 years. We met in high school, and […]

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#217: The Almost-Doctor with the Almost-Boyfriend

Dear Captain Awkward, So there’s this guy, let’s call him James. We have been friends for several years and in this, our last year of medical school, have slowly gone from drunken making-out, to friends with benefits, to casually dating. It has been exciting and awesome, but we were both more or less expecting this […]

#216: I broke up with someone because she cheated on me. Was that sexist?

First, I love this: How do work up the courage to kiss the girl I like? Second, a letter: Hail to thee, O Captain, Perhaps I’m taking a different approach than other letter writers, but I would like your thoughts and judgment on events that quickly transpired this weekend. I had little time to deliberate, […]

#215: How do I help my friend realize she is lovely?

Dear Captain Awkward I have two friends, let’s call them Jane and John, who have been in a long distance relationship for the last few months. She’s 18, he’s 25 and they met online – same way I met both of them. They decided to meet face to face but at the last minute Jane […]

#214: An object lesson in “overthinking it.”

Dear Captain Awkward, I’m sure there’s a short and sweet solution to this one, but I can’t seem to see it. Perhaps the Awkward Army can advise? The very short version: There’s a guy, and he’s cool, and I’d like to maybe get coffee with him sometime and see what happens. I know, I know, […]

#213 : Am I weirding everyone out by not being gay?

I’m happy to say that this is my most pressing question about sex ‘n’ relationships ‘n’ stuff right now.  The short version is that a lot of people who don’t know me that well aren’t sure whether I’m lesbian, straight, or somewhere in between.  I’m sure where I am (straight) but I also like the […]

#212: Bad connection. Try again later.

Dear Captain Awkward, I’m 24, a lady, and I have never been in any kind of a romantic relationship before, until now. I think I’m fucking everything up. Here’s the lay of the awkward; Some mutual friends of ours set me up on a blind date about a month ago and we really hit it […]

#211: If my friend has feelings for me, it is only logical that I return them.

Dear Captain Awkward, Geeks of the feather, flock together. It’s an obvious thing within my wonderful friends circle, but it’s not horrible. All the people I consider to be good friends are socially inept and awkward somehow. Not to a debilitating or super-creepy level, but we’re all definitely the oddballs who will miss a handful […]

#210: I feel guilty because I don’t like my dad.

Hey Captain Awkward. You might be the wrong person to direct this question to, but I don’t really know who else to ask. I don’t really like my dad and it makes me feel guilty and weird and anxious. Part of it is that he makes me uncomfortable in a way that feels sexual. I’ve […]

#209: My mom is pressuring me to invite my molester to my wedding, and it sucks BIG TIME.

Hello everyone. Captain Awkward here. This post involves some deeply harrowing no-good shit, so we’re putting everything behind a cut. Also of note: This post, you’ll notice the byline above, is a guest contribution of Marie (of The House is full of EVIL BEES fame), now promoted to Private First Class in the Awkward Army. […]


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