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Dating

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 […]

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#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 […]

#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). […]

#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 […]

#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 […]

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 […]

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