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#563: I have a hard enough time making friends for myself. How do I navigate the special hell that is arranging playdates for my children?

Hi there Captain! I’m a 36 year-old mom of two adorable boys (6 and 2). I also have no friends. I’m not entirely OK with not having friends, but I’ve gotten used to it over the past 30 years or so of not-having-friends-ness. What I’m less OK with is that my Big Guy seems to […]

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It Came From The Search Terms, April Showers Edition

Every month(ish) I answer the questions people typed into search engines to find this blog. Except for adding punctuation, I don’t change the wording. Enjoy! 1. “Mother-in-law hates me. How do I tell her I’m pregnant?” That sounds like a job for your spouse, her (presumably) son, who should be doing all or most of […]

#558: Help I’m boring

Hi Captain Awkward (or any other lovely affiliated blogger kind enough to take this letter on), I’m a very boring person. I used to think I was creative and interesting, but I find that all I really do is mindlessly consume media. I read online constantly (articles, blogs, forums, etc) but almost never post anything […]

It Came From The Search Terms: SMARCH

The monthly(ish) roundup of the questions people type into search engines to find this blog. 1. “My partner thinks I have genital warts but I have herpes what do I do?” Both of you should get a full STI screen, if you haven’t already, and talk about whatever you find there. (‘Cause maybe it’s both). […]

#553 I’m following my heart, so why won’t my friends root for me?

Dear Captain Awkward, I married my college boyfriend T three years ago, but our marriage became pretty awful. This past summer I went to a month-long program for my job and met M, who is honestly the most amazing person I’ve ever known. He gets me in a way no guy ever has. When we […]

#552: Crossing Paths with Darth-of-Old

Hello, nice people of the internet! I took your generous Pledge Drive donations and finally bought myself a reliable, working computer. I CAN WRITE AGAIN! February is over and my 2-week sinus-infection-shitbeast-respiratory-thing-from-hell seems to be lifting. I CAN WRITE AGAIN! HI IT IS NICE TO SEE YOU ALL I MISSED YOU AND HOPE YOU ARE […]

PSA for the shy, sexually inexperienced, maybe-queer, maybe-bi, maybe-asexual ladies who send me letters about finding someone to snuggle and/or date:

YOU. ARE. LEGION. You are not alone in writing a (usually beautifully written, well-spelled) note about how you are looking for someone to hang out with and maybe make out with and cuddle but without pressure or expectation of doing more. You are not alone in feeling like traditional “dating” situations and advice don’t work […]

#546: Counter-Intuitive Friendship Fixing Advice: The Be Nice To Yourself Project

Dear Captain Awkward: My very best friend and roommate acquired a boyfriend and I’ve become a bitter, jealous, monster. I never, ever thought I would be one of those jealous, possessive friends, but it turns out I am. We are very wonderful friends and roommates and are happy and enjoy each other about 90% of […]

#545: My old friend was great when we lived close, but has gotten very mean from a distance.

Dear Captain Awkward, When I was in university, we had a tightly knit group of five friends, and I’m glad to say that group has stood time and is still together. Two years ago, I moved abroad to a different country and I only see the rest of the group occasionally, around three or four […]

#539 “Old New Friends”

It’s day 2 of the Winter Pledge Drive, so if you feel like dropping a few dollars in the tip jar, here’s the link. Thanks to all who have given already; it really makes a difference in my life. Today’s question is also on the theme of forgiveness and repair Hi Captain! I have a […]


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