Dear Captain Awkward, I am so scared. I keep messing things up financially. I just don't know how to do it. How to DO MONEY. But it's a paradox, because I am earning a decent amount. It's a paradox about which I feel rather ashamed, because I am aware of my privilege. I come from … Continue reading Guest Post: #909 “I Should Be Able To Do Money…But I Can’t”
Hello Captain Awkward, I have a long question about how to get a family member to pay back the money they owe you. First bit of background: I recently got married and moved to another country VERY far away. It's been almost a year now and really wonderful (except where my sister is concerned). My … Continue reading #892: How do I get my sister to pay me the money she owes me?
Dear Captain Awkward, I have a great, strong, smart female friend who has fallen head over heels for her boyfriend. They've been dating for under a year but already live together. This friend has been attending a weekly trivia night with us now for over a year. When the new guy came on the scene … Continue reading #806 Trivia Night & Drunk Math
Can I say how much I love this LW's original email subject line: "A Soap Opera Problem--families torn apart over money, demanding parents, undutiful daughters who are me, sons trying to bear the whole burden." Yeah!!!! Dear Captain Awkward, I'd really appreciate your advice on a family problem. Dad grew up privileged, then was mostly-disinherited … Continue reading #800: F is for “Family, Finances & Feelings.” D is for “Disengage.”
Ahoy Captain, Several years ago my fiance and I started hanging out with a guy named Devon*. At the time we started hanging out with Devon he was having a lot of personal problems. He was living in a hotel that he could barely pay for, slept all day and stayed up all night, and … Continue reading #752: “My roommate is acting like my teenaged son.”
Ahoy, Captain! My partner and I have been together for about three years now. We don't live together, but lately my partner has been saying that he would like to start cohabiting - not necessarily immediately, just at some point. Mostly I'm the one saying "let's not." There's a few reasons for that, but a … Continue reading #608: My partner wants to move in together, but I don’t feel comfortable combining finances with him.
Ahoy Captain, I'm writing this after reading about the LW who kept getting stuck with the check. I'm in the inverse of a similar situation, and I'm not sure of the best approach. I've just started a job in an awesome place with a bunch of wonderful, appropriately friendly co-workers. Apart from loving what I … Continue reading #601 and #602: Bodies and money and shame when you have nothing to be ashamed of.
Dear Captain, I was wondering if you could spare some advice on how to go dutch (AKA 'make-people-pay-their-share) with people who are 'sensitive' (where 'sensitive' is in the ''easily-offended' way, not the 'sensitive-they'll-figure-it-out-with-only-a-little-prompting' way.) And these 'people' are all members of my in-law family which I would described as a relationships which are 'generally-pretty-friendly' but … Continue reading #586: Splitting the bill with people who always forget their wallet.
Four letters about The Guy Who Would Be Perfect If Not For That One Dealbreaker Thing. I didn't publish the 5th of this ilk that came in this week, which was about a perpetually-unemployed-and-not-trying, bad-in-bed man who was also mean. That one was too easy (Bees! Run!). These are harder because people don't have to … Continue reading #573, #574, #575 and #576: Applying the Sheelzebub Principle
Dear Captain, I have a dilemma. I’ve been having a terrible year in 2014 (and 2013 was pretty shit also!) My husband and I have been having a rocky year in our marriage, I have just started an antidepressant to deal with my ongoing and dangerous depression, we have a $25,000 fee to pay to … Continue reading #564: I’m dreading the prospect of a summer houseguest, but I feel like I can’t say no.