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#381: How do I tell my sad friend I’m getting engaged?
Dear Captain Awkward, So, this friend is someone I’ve known for nearly a decade. We went to college together, we were roommates during and after college together, we’ve collaborated on work together,...
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#385: My ex-friend and his bullshit lies.
Hey Captain Awkward… So! I used to be BFF with this guy. I eventually ended things after it took a turn for the weird – he became incredibly demanding of my time and attention and started telling me...
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#386: Facing down a predator.
Behind a cut for discussions of sexual abuse. Hi Captain Awkward, I don’t know if you appreciate trigger warnings, since most of what you deal with sounds like it would apply, but this letter is...
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#387: The coffee made me do it.
Hi Captain Awkward, I have a best friend who’s already like a brother to me. He’s married and they’re expecting their first child. However he’s still struggling to make his ends meet. Hence I only get...
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#388: Please let me go.
Dear Captain Awkward, I have decided to end my 4-year relationship with my boyfriend. Throughout the last 4 years, despite my best efforts to convince myself, I have never been truly passionate and...
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#401: I can’t tell whether my girlfriend wants to have sex with me. (Spoiler:...
As of 12/7 comments on this discussion are closed. Hello Captain! I need a script for talking to my girlfriend about what she wants in bed. She’s eighteen and I’m twenty and we’ve been together for...
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#404: My thief of a dad is going to be at my sister’s wedding.
Dear Captain Awkward, In a few months, my big sister’s getting married, and I’m a bridesmaid. Awesome! The problem is that my estranged father will be there, and I legit cannot be around him. My...
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#407: Was I “leading this guy on” when I asked him if we could be friends and...
If you had met up with your ex that day, this would have been the expression on his face. Still feel guilty? Hi! This is very sweet, right? But don’t spring it on someone the first or second time you...
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#418: My mom wants me to prioritize caring for my sister over caring for...
Hey Capt., Cliff notes. My sister got pregnant three years in a row, giving birth to three healthy babies by c-section. With baby 1 she was put into bed rest almost immediately and I was assigned to...
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#423 & #424: Relationships aren’t transitive.
Dear Captain Awkward I’m currently in a happy poly relationship where me and this other individual are dating the same person (X) whom we both have a primary relationship with (the girl and I have a...
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#426 & #427: E-blasts from the past.
Hey Captain Awkward, I am the LW of the “how do I break up with my mean ex who scares me?” Recently I have received harassing emails and blog comments from his new girlfriend telling me I am a liar and...
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#434: Just me and my shadow, trying to network.
Hi Captain Awkward, A few months ago, I met a guy who works in my field through a professional networking event. Since then, I have noticed that he has such a brutal case of White Knight Syndrome that...
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#435: Getting the silent treatment for an honest mistake.
Dear Captain Awkward: Quick backstory: my mom and stepdad babysit my daughter for free one afternoon a week while I work (I telecommute the rest of the time). My mother offered to do it right after my...
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#443: Ending the reign of FEELINGSTERROR
Morning, Dear Captain: I have a friend who I suspect is battling some pretty severe anxiety/depression problems. It makes her extremely defensive and difficult to be around, because literally anything...
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Cohabitation Situations: Ambivalence Deliverance (#451) & Eviction...
Before we jump into sad, serious things, Gollum dreamed a dream (of coming to your party?) Courtesy of my friend @spyscribe. You guys watch The Lizzie Bennet Diaries, right? Now, some letters about...
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#460: Boundaries are good, even if other people don’t enjoy it when you set...
This is a very smart post on moving on and setting boundaries with an ex from Jenn Vicious at In Our Words: “There’s this thing that sometimes happens when people break up but still care about each...
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#461: My partner makes hurtful jokes about my health situation.
Dear Captain Awkward: I have had a very complex life in the last couple of years. I have gone from having a fairly normal life in regards to health and then I went on dialysis. Since that point I now...
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London Meetup + #462: When is it time to cut off communication with abusive...
Reminder, monthly London meetup is tomorrow. Sorry for not posting this sooner, guys! It’s been the week of 1000 meetings. Dear Awkward Army, London meetup this weekend, 23rd March! All welcome. 11:00...
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#465: Life after Darth
Image from likecool.com Hi there, An online friend and I were innocent email buds. One day, we start DMing which leads to texting/phone call. It gets sexual. Tells me he has a live in girlfriend but...
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#468 and #469: “Hey, knock it off”, or, Constructive Conflict, Continued.
Jolly’s great comment to Monday’s post is going to be very relevant to these seemingly very different questions: “You also don’t necessarily have to bring some of these things up in one big...
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