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 and lost his job when I was a
kid. Instead of retrenching, he incurred debt. Mom demands luxuries,
cheats, and is an alcoholic prone to rages. Now Dad asks me and my
brother A for money constantly, always at crisis moments.

Dad always believes that his financial issues will be over soon.
Unfortunately there’s a company he has a part in being sold, meaning
he might get some money one day—there’s some basis in reality but not
enough. He refuses to sell his house, because he wouldn’t get enough
money, and claims to be always economising because he doesn’t go on
holidays though Mom does and he belongs to an elite gentlemen’s club.

A and I have precarious jobs in which we are paid in irregular lump
sums, so we have the money to give him. We both consider ourselves
lucky. The emotional toll of these emergency requests is huge. We also
cannot afford them. Over 5 years, between us we’ve given Dad over

I wrote to Dad saying his behaviour is disordered and deeply hurting
us. He refused to go to his bank with us, blamed A for not giving him
enough, and hardly seemed to have read my message. He’s past hearing.
Saying he’s a good father otherwise is asking Mrs Lincoln how she
enjoyed the play otherwise.

I tried cutting him off altogether years ago: it ended when my
siblings exerted pressure on me to do a family Christmas. I’m proud of
my siblings (A, B & C, all younger) for getting through our childhood,
but I’m the one who rocks the boat. A gives money to Dad without me
knowing, so as not to risk alienating me. A has a more optimistic view
of the situation. My sister B agrees with me mostly, but B and C are
more sheltered (by me and A). C is college age, still living with my
parents. He’s begun suffering from panic attacks. He plans to get out
of the house next year: I’ll help him.

I’m considering not going home this Christmas, but I know it’ll upset
my siblings and I want to see C as neither of us is great at
long-distance. If I do go I’d like a script for talking to A, and my
other siblings, about this, and to make a plan for us going forward,
in how we’re going to react to my parents and stick together. I’ve
asked A to promise me not to give money to my father without telling
me: so far he hasn’t promised. It would make me happy if I could get A
to agree on no more money given directly to my father.

Thank you so much.

–Saving Only Siblings

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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 seems to have had a minor drug problem. Fiance and I, seeing that he was in a difficult situation, invited him to come live with us for a few months.

It’s been two years.

I like Devon, a lot, and I enjoy hanging out with him. He’s a sweet guy and being around him is simple and fun. I don’t necessarily want him to move out, which I guess is good for me because it doesn’t look like he’s going to any time soon.

Devon is now has a job, doesn’t do drugs, and kinda sorta pays rent *sometimes*.

My real problem, though, is housework.

I think it’s only fair that Devon take some responsibility for the house work. I’ve tried to talk to him about this so many times I’ve lost count. He always brushes me off, says he’ll do it ‘later’, he’s tired from work, or that the dishes in the sink aren’t ‘his’.

These excuses are childish the point of hilarity. I don’t argue about whose shit stain is whose on the toilet when I clean it, why does it matter whose dishes they are??. I brought it up again last night and he said “well I keep my room clean”. Well yeah, that’s all fine and dandy, I don’t expect him to clean my bedroom. I DO expect him to help with the kitchen and bathroom, which everyone uses every bloody day.

I’ve tried multiple tactics:

I’ve tried telling him what is expected of his as a member of our household

I’ve tried gentle encouragement

I’ve tried reasoning with him

I’ve tried yelling at him

I’ve tried explaining that it’s not fair for all the housework to fall on my shoulders since I’m not a damn maid

I have even tried boycotting all chores in the hopes that the revolting state of the house would encourage Devon to pitch it. The only outcome of that is, after a few weeks, the house (especially the bathroom) became so disgusting I couldn’t stand it anymore and I cleaned it myself.

What am I supposed to do about the cleaning short of kicking him out? I feel like I have tried everything. It’s driving me completely batty. In the past few months I don’t even bother doing more then a perfunctory clean because everything is always messed up 5 minutes later anyway. Sort of like in that episode of The Simpsons, “Bart Gets an Elephant” where the kitchen door opens on a clean kitchen, swings closed, and opens messy (sorry couldn’t find the gif) [Ed note: FOUND IT]!

Kitchen from Bart Gets An Elephant


I can hear him cooking in the kitchen now and just dread the stupid mess of discarded vegetable parts that will be everywhere in about 20 minutes.

I have been very explicit about my expectations but he just doesn’t hear it. I’ve even asked my fiance to speak to him about it in the hopes that maybe he would be more inclined to listen to an older man. Nothing. Same brush off.


Molly Maid

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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 major one is financial.

I work full time at a higher wage than my partner, who works part time. He’s frequently out of money by the time his next paycheque comes, while I can count on one hand the number of times I’ve been straight-up broke, even when our incomes were more comparable. When we go out, I usually pay, which is not a problem for me; I’ve also occasionally lent him money for things he really needed, like a bus pass at the beginning of the month, and when something is clearly expressed as a loan, he’s fairly good about paying me back. However, I’m not totally on board with the way he prioritizes his spending. For example, his bed frame has been falling apart for the last year and a half. He said he couldn’t afford to replace it – but in that time, he’s definitely spent more than the price of a cheap Ikea bed (let alone a Craigslist find) on books and games.

I’m not criticizing him for spending his money on things he likes. It is, after all, his money! He’s a grown-ass man and he earned it. I’m also not his mom, and neither he nor I wants me to nag him about financial responsibility. Basically, I just slap a big ol’ Not My Problem sticker on about 90% of his cash flow crap and move on with my life.

My concern is that if we do move in together, I will start shouldering not just most of our financial responsibilities, in accordance with my larger earnings, but ALL of them. I worry that if we did get together, he’d know that the rent would get paid and food would get bought no matter what, so why not go ahead and spend whatever he feels like – not inconsistent with what I know about his spending habits. He’s also got a big pile of student loan debt, and if we’re cohabiting and eventually end up being common-law, I don’t want to take on responsibility for that.

It feels cold, but basically, I’m afraid that moving in with my partner will mean taking a financial hit. It’s not necessarily one that I can’t afford, but it is one that I don’t want.

I’m not immediately on fire to move in with my partner right now – it probably wouldn’t happen anyway, for a number of reasons – but should I mention this to him as part of my reasoning? If so, how do I do that? And if we do decide to make that commitment together, how do we address this problem as a couple?

Many thanks,

Not Subsidizing Anyone

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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 do there, this job will (slowly) get me out of a pretty grim financial situation created by student loans and intermittent work over the past two years.  For now, though, I’m on a skeleton budget and can’t afford much by way of unnecessary stuff, which is where the problem starts.  My co-workers have all worked together for a while, and they do this cool thing were they go out to lunch together a lot and take turns either paying for lunch, or collecting money from the office to run out and get food.  They invite me frequently, and once or twice have covered me for lunch on the rare occasion I forgot to pack one. I’d love to participate, but I can’t at the moment due to being behind on a lot of crucial bills.

The trouble is that it’s getting to the point were it feels really weird to be constantly opting out of these lunches, especially since we’re a small office, and the fact that I don’t volunteer to pitch in for food runs is creating some very awkward situations were I’m constantly removing myself from the rest of the group.  I know I’m coming across as either stingy or unfriendly, which concerns me because I really want to make this job a pleasant environment.  But it’s realistically going to be a few months before I can afford to do this, and I don’t want to explain my financial situation to my colleagues.  Are there any scripts or tips you and the awkward army know of to navigate this embarrassing situation?


Economic Casualty

Dear Economic Casualty:

The first ever Captain Awkward reader question was about a similar topic, with friends and money and eating out. So, hey! We’ve come a long way.

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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 coated with a thick layer of ‘don’t-rock-the-boat’.

I don’t mind being generous (and I come from a family of similar) but I’m finding it increasingly difficult to deal with my in’s who are all financially well-off but when a bill comes around for a shared service are always suddenly stuck by the need to ‘go to the bathroom’ or ‘get something from the car’, have forgotten wallets, don’t have cash on them right now, will ‘get the next round’ or ‘are really short this week’.

I’ve tried some techniques in the past –

  • Pre-arranging payment methods beforehand (these get ‘forgotten’, wrong payment is brought, or guilt is brought out ‘I didn’t know it was so expensive here’)
  • Only bring a set amount of cash or trying to remind them that I had the last round (the ‘bring only a set amount’ has been a disaster – its resulted in long moments standing awkwardly round the till in silence with everyone looking at me while I muttered pathetically “Sorry, I only brought enough for me” or worse, they have all walked out/vanished leaving the bill unpaid. A member went back and paid it once we realized it hadn’t been covered but the experience was very unpleasant. The ‘I had the last round’ is met with excuses similar to if payment is pre-arranged).
  • Ask my husband to speak with HIS family about this. This had been met with either apathy and sympathy but no results. (“Yeah, they are like that and it is annoying. But that’s just how they are.”) (“Just don’t go out with them then.”)

I like spending time with my in-law family and we do a lot of other free fun things together but I’d also love to occasionally go out for a meal, see a movie or get my nails done in their company without having the pay for the pleasure.



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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 be evil to be not quite right for you.

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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 our condo I still don’t know how we’ll finance, and I have been balancing full-time work and full-time school schedule for nine months. Basically, I’m tired to the bone physically and emotionally.

My husband, Jack*, and I are currently in the process of going through some counseling and things on that front seem positive and hopeful. The problem is, he recently asked me if his brother can come stay with us from June to August to work in our town. Jack’s brother, Bill*, along with the rest of his family members, live in a faraway province with little economic action. We live in a booming economy with many jobs, especially in Bill’s area of interest.

I had not been planning to take any courses over the summer and was looking forward to some rare downtime and the chance to recover and feel like myself again. With an air mattress in the basement serving as a “spare room” and only one shower, living area and kitchen, it’s inevitable that Bill would end up encroaching on our space. Although he’s in college now he’s still a teenager, so I’m also concerned about his cleaning ability or lack thereof. Plus, frankly, I just don’t want to deal with a houseguest for the whole summer!

Jack misses his family a great deal. This would be a great chance for him to catch up with his brother and bond, to say nothing of the opportunity for Bill to build work experience in his field. I can’t help but feel like the bad guy if I say no, but I’m already mourning my lost, private summer full of reconnecting with Jack and having plenty of alone time. Should I kibosh the trip and live with the guilt? Say yes and quietly resent every moment? PLEASE SEND HELP.

Houseguest versus Hag

*all names changed

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