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#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 […]

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#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 […]

#547: “Is it my anxiety or is my relationship dodgy?” Spoiler: Holy fuckshit, IT’S THE DODGIEST

Comments are closed as of 2/9 Hi Captain, I need your help. I don’t know if I’m in a shitty relationship or if bad things just keep happening to us. I’ve been dating a guy for eight months. We fell in love very quickly and very intensely. The first period was very happy but I […]

#542: The Butt Dial of Jealousy and Specious Accusations

We haven’t had a gif party or a “Yo, maybe you are way cooler than that person you are dating” thread in a while, so, here you go. Dear Captain Awkward: My partner of 5 years moved 200 miles away last week for a job. I’m sad he’s gone and I’m missing him, but I […]

#541: What kind of financial “help” do I “owe” my uncle?

My feet are cold, but my heart is warm thanks to the generosity of the Winter Pledge Drive contributors. Thank you so much! Support the site if you can! Today’s letter is about money and family and when those things come together in a manipulative and possibly sinister way. Dear Captain Awkward, My parents passed […]

#538: Forgiving a Friend’s Darth Vader

Dear Captain, How obligated are we to try and forgive our friend’s significant others for the harm they have caused in the past? To make a long story short, my friend A started dating person B.  I wasn’t wild about B, but I wasn’t the one dating him, and our casual interactions initially seemed fine, […]

#536: My face is a blushing traitor, and creepy older dudes have definitely noticed.

Hey Cap’n & Crew, Fairly straightforward question here. Sometimes my face can be a traitor…it turns bright red and gets really hot at any extreme emotion, particularly embarrassment. I am sure many people can relate! So here’s the question: What would you suggest for scripts for when someone (99.9% of the time it’s an older […]

#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 […]

#529: (un)Fun with tenses: You HAD an abuser. You HAVE a stalker.

This post is behind a cut due to intense discussion of sexual violence and stalking behavior.


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