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Archive | July 2012

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#316: Reaching out to an ex

Dear Captain Awkward,  At the beginning of this year, after much agonising and a deep depression lasting several months, I broke up with J., my boyfriend of three years. We lived together, we had friends in common – it was messy, but I tried very hard to be honest with him. This included telling him […]

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#315: The boundary-crossing neighbor

Hi, Captain Awkward, My Beloved and I bought a house around three years ago, which shares a driveway with another neighbor (the property line literally goes right down the center of the drive).  We were very optimistic about this, initially, as she seemed a very charming and outgoing lady.  For the most part, our relationship […]

#313 & #314: Broken Friendships

Should there ever be a Captain Awkward Dot Com Meetup, I will acquire a bunch of these coloring books and the big boxes of crayons (and some silver and gold gel pens) and have a table where people can hang out and color. Right? Right. Thanks, Cleolinda! Today’s letters are on the less happy topics […]

#312: Aftermath

Hello! I took a few days off to work at my real job and go to the movies and read books and hang out with my boyfriend. It was awesome and I will be doing more of that + shooting a short film in August. Old business: If you donated to the pledge drive via […]

#311: My wife freaks out whenever I’m away from her.

Dear Captain Awkward,  My wife has contributed so much to my life.  In college, I made a difficult transition from developmentally-challenged homeschooled Evangelical missionary wannabe to Libertarian to a proto-value-actual-people-and-outcomes-and-recognize-cognitive-biases-and-reject-satisfying-internal-consistencies-ist.  The latter doesn’t actually have content; I was shattered and adrift, trying to find my voice.  Hell, discovering the phrase, “find my voice” was actually […]

#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 […]

#308: I feel like I don’t deserve my partner’s support of my artistic dreams.

Dear Captain, So here’s the deal: I’m married, and living with someone who is incredibly smart and hard working. He has so many mad skills that he doesn’t even need to submit applications to get a job. By comparison I have a degree in something I realized (after 4 years) isn’t really my thing and […]

#307: Chemistry!

Dear Captain Awkward; I have liked this girl for a while now, or at least we seem to have strong chemistry. Sometimes we hang out and there are these tense moments of “Are we gonna kiss?” that I think are on both sides. The caveat is that she is already dating someone (who sounds kind […]

#306 Secrets, Lies, and Stephanie

Dear Captain Awkward, I’ve been in a relationship with a kind, caring man for the past two years. This is my first serious relationship (yay!) and his second. I’ve had some experience with casual dating and casual sex prior to meeting my boyfriend, but he hasn’t had as much, so his previous relationship is his main point of reference. […]

#305: “Quit helping so much! I’m not going to fall in love with you.”

Dear Captain, I am having a hard time finding my words, or finding words that will get through.  Here’s the situation: I am a thirty-something female who has, after several years of struggle, come to terms with her complete lack of sexuality.  I have dated men, and I have dated a woman, and all in […]


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