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Tag Archive | darth vader

#533: Can I bar my son’s unlikeable girlfriend from family events?

Dear Captain Awkward: My 27 year old son has been in a relationship with his girlfriend for about 18 months. He was living with a friend until a couple months ago, when he and his girlfriend moved to an apartment. Before the move, his friend came to see my husband and I to talk about […]

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#520: Getting your stuff back from a Darth Vader ex

Dear Captain & Co., I’m in a wonderful relationship, but we’ve got a Darth Vader ex-girlfriend lurking on the sidelines. When we first started dating she behaved horribly: showing up on his lawn screaming suicide threats when she found out I was over, harassing him for months, hacking his email to get my phone number […]

#511: When you find out that someone you care about is mean.

Dear Captain Awkward: How do I see the whole of a person? Hello! I was hoping you could help me with something. There is a guy at uni I am friends with, who has depression. Over the past semester at uni, we have grown very close, mostly on the basis of me becoming the person […]

#465: Life after Darth

Hi there, An online friend and I were innocent email buds. One day, we start DMing which leads to texting/phone call. It gets sexual. Tells me he has a live in girlfriend but doesn’t ever say “maybe we shouldn’t go there.” It progresses to constantly talking, texting, gchatting. 2 weeks after we started he flew […]

#454: Darth Vader is a tricksy hobbit.

Hello, Citizens of Friday. First order of business, this great nod of solidarity for the socially awkward from Dorothy Parker. ‎”Those who have mastered etiquette, who are entirely, impeccably right, would seem to arrive at a point of exquisite dullness.” -Dorothy Parker Second order of business: This great post from The Pervocracy, “How To Have Sex […]

#269: Anxiety, chemistry, and second chances.

Dear Captain Awkward: I’m caught in my own head and could use a guide to get out of it. There’s a gentleman who’s recently come back into my life. We first connected two years ago when he was separated from his (second) wife and while we talked all of the time and hung out a […]

#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 […]

#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 […]


I started this blog in the middle of an email thread with my lady friends about deciding where to eat brunch. (Answer: Wave) I had flirted with blogging before, starting a semi-professional blog (completely made obsolete by the awesome Short of the Week) and a food blog (Pretty recipes! Sometimes read by 20 people a […]


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