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#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 […]

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#467: How do I help my partner communicate better with his family?

Dear Cap’n, I don’t know how best to help my DH. This message follows us having a long, slightly drunk but happy and loving chat about his life. DH’s family history is complicated. His upbringing includes some things which, when we talk about them, he agrees were “probably abuse”, but explains that he’s somewhat normalised […]

Cohabitation Situations: Ambivalence Deliverance (#451) & Eviction Prescription (#452)

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 living situations gone bad (#451) and very, very bad (#452). Dearest Captain, I need some help with relationship ambivalence. It’s been 3 years […]

#418: My mom wants me to prioritize caring for my sister over caring for myself. What do I do?

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 make sure she didn’t jeopardize her or the baby’s health. This was a difficult task only made worse […]

#407: Was I “leading this guy on” when I asked him if we could be friends and then he suddenly showed up where I live?

Hi! This is very sweet, right? But don’t spring it on someone the first or second time you meet them. Friend-date people for a little while and if you’re meant to be friends you will totally figure it out. Dear Captain Awkward: I ended my first romantic relationship earlier this year. I’m in my early […]

#371: “How do I end this misery?”

Dear Captain Awkward: About ten months ago, I started a relationship (a really-long-distance relationship with someone I met on a website). At first, and I have to be honest here, I was just fooling around, I couldn’t believe that you could actually fell in love with someone you don’t even know. He was a “good […]

#335: How do I set a boundary with my friend without hurting her feelings?

Dear Captain Awkward, I have a best friend.  We’ve known each other for a long time, gone through some really rough times together as we both coped with mental illness, toxic families, financial hardship and general shenanigans.  Being single ladies who are at the asexual end of the scale, we share a house, and have […]

#315: The boundary-crossing neighbor

Hi, Captain Awkward, My Beloved and I bought a house around three years ago, which shares a driveway with another neighbor (the property line literally goes right down the center of the drive).  We were very optimistic about this, initially, as she seemed a very charming and outgoing lady.  For the most part, our relationship […]

#305: “Quit helping so much! I’m not going to fall in love with you.”

Dear Captain, I am having a hard time finding my words, or finding words that will get through.  Here’s the situation: I am a thirty-something female who has, after several years of struggle, come to terms with her complete lack of sexuality.  I have dated men, and I have dated a woman, and all in […]

#258 = #191 + Bridesmaidery

This is a follow-up to this post: http://captainawkward.com/2012/02/15/191-annual-reminder-time-get-your-teeth-cleaned-get-your-eyesnaughty-bits-checked-and-stop-hanging-out-with-crappy-people/ Dear Captain Awkward: First of all, I want to thank you and your commenters SO MUCH for being such kick-ass human beings and providing so much support and insight into the situation when I was so blind to what was going on. If I could, I’d invite […]

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