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rejection

#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 […]

#559: Does “can’t be in a relationship right now” always mean “…with you”? Spoiler: Yup. Sorry.

Dear sifters of potentially-answerable awkwardness, I’ve had a lover of the very best kind for the past ~9 months, healthiest relationship I’ve ever been in, and we both had started to talk about, you know… we could see us together for a long time. I feel respected and heard and loved and the sex is […]

#557: That’s just one dude’s opinion/Annual reminder that “why did you break up with me?” is not a question you actually want answered.

Dear Captain Awkward: About two weeks ago, I was broken up with by my then-boyfriend of nearly two years, P. I did not see it coming, at all. A week before, he had invited me to his family’s reunion in the summer, and he had spent the previous weekend with me. P and I met […]

#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 […]

#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 […]

#535: Forgiveness, patience, and other traps.

Hey there Captain Awkward, I don’t normally post these things, but I’m taking a big step and reaching out to you in the hopes that I can get some useful (if not probably obvious) advice from you.   I have been in a relationship with a man 8 years younger than me for the past […]

#534: Cancer support or pity dating?

Dear Captain Awkward, Recently, an old friend began messaging me on social media to tell me that he had cancer. Initially, I was shocked to hear that he’d been diagnosed with (an unspecified) form of cancer. He’s the same age as I am (24) and, from what I’d seen when we were closer, led an […]

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