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Overthinking It

#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 […]

#560: It’s *your* party, so why would you invite people who put you on edge?

Dear Captain Awkward, I’m organising a house party for my 21st birthday, but I’ve run into a dilemma which I don’t know how to resolve. Backstory is, I was dating this woman, let’s call her X, for over half a year. We split up before January. It was my first real relationship and the breakup […]

#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 […]

#555: Carts, Horses, and the Order of Operations

Dear Captain Awkward: How bad is it to get involved with a new person when I am still very hung up on someone else? Someone not available to me, but still part of my friend group? Even though I am still in love with him, I no longer hold out hope that we can be […]

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). […]

#554: The Mirror of Confusion

Dear Captain Awkward, I happen to really like a guy who is the most confusing man I’ve ever met. I met Matt( fake name don’t worry) through my best friend. She is the type of person who finds loads of guys attractive and usually likes me to meet them so she can a) get my […]

#551: What does it mean when a dating partner is “worried that they might be using me?”

Dear Captain Awkward, I’m a white ciswoman in my late twenties living in the Midwestern US. I’ve had a free online dating account for a while, having marginal success with short term dating but nothing that’s really led anywhere. My only *serious* relationship ended five years ago, after less than two years. I’ve come to […]

#548: I met a cool person to flirt with and I’m scared of what to do next.

Dear Captain Awkward, So I met a girl last night, one I’ve run into occasionally when the orbits of our respective circles come into gravitational alignment. We spent the time chatting together and exchanged numbers afterwards. I have zero experience with romantic relationships, but what little knowledge I’ve accumulated from rom-coms and trashy novels leads […]

#543: I can’t sleep because my first prospect for a “real” relationship might secretly be a furry.

Hi Captain, I’m afraid I’ve ruined something. I don’t feel comfortable talking with my support team about this yet for reasons that will soon be apparent. Backstory: I am a woman in my later twenties whose longest relationship ever lasted 6 months (and honestly it’s stretching it to call it a relationship). This is not […]

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