Author Archives: JenniferP

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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I’ve got a piece up on awkward holiday conversations at BuzzFeed this week.

If you’re a new reader, here’s some stuff you might like to know:



[Video: A French bulldog puppy rolls around on its back trying to flip over]

If you’re not feeling this time of year, this is your place to commiserate with others. I am not sure I’m getting to any more “holiday” questions this month, so you may want to post the short version here instead for others’ feedback.

Regular commenting policies apply, with some reminders:

  • BE KIND.
  • This remains a “No Diet/Weight Loss Talk” zone.
  • If you’ve got a lot to say, it’s okay to give a brief intro to a topic & then link to a longer version on your own site.
  • Don’t yum other people’s yuck. If you love the holidays, your thread is over here.
  • If you find yourself arguing back and forth with another commenter about their own experiences….why? Why are you doing that with your time?
  • BE KIND.

[Video: A Great Dane and a deer are best friends who snuggle and frolic]

If you love this time of year, this is your thread. Whatcha cooking? Who are you excited to see? What are you thankful for? What’s a favorite tradition that your family & friends have? Got any cool decorating plans?

Usual commenting rules apply, with this brief review:

  • BE KIND.
  • Don’t talk about calories or weight loss or diet stuff.
  • Don’t yuck other people’s yum. If you hate someone else’s idea, or it won’t work for you, they don’t need to know!
  • You can share longer thoughts/posts…by giving us a brief intro and then linking to the rest on your own site.
  • If you hate the holidays and everything sucks right now, I made you a thread, too. This is isn’t that one, so don’t cross the streams.
  • BE KIND.




The post title was the subject of the email exactly as it came to my inbox. That will be important later.

Hey there Captain,

I recently moved to a job that not only frees up more time to focus on schooling, but pays better. On the last day at my previous job, a girl I’d occasionally worked with and spoken with in the breakroom, asked for my number.

If her interest wasn’t obvious enough, as I walked out the door for the final time, her question was whether I had a girlfriend. I told her no, and to my amusement, her reply was that she’d text me. Needless to say, I got a text bright and early the next morning and we’ve been texting a bit.

She’s nice and I get along well with her, but I’m unsure about making the choice to date her. There are a few things I see as obstacles, but can be worked through.

She’s the daughter of my previous manager. Introductions as a boyfriend would be awkward because my manager didn’t want me to leave. I worked hard, kept a positive outlook, and somehow managed to get along with even the prickly people there. I lit up many people in that glum environment.

While texting, she obviously wanted to get to know me better, so I took the lead, organized a meetup, and we had fun, went for coffee, and wandered around the mall.

It was a great chance to get a feel for her personality, lifestyle, relationships, and maturity. When I asked her what she enjoys doing, she said that she didn’t really have any hobbies, but that she enjoys hanging out.

During the meetup, she spoke mostly about how she doesn’t like work, her parents are always mad at her, her exes (about two or three by how she spoke about them), and her life in general. After the meetup, she told me she had fun and wants to meetup again next week (the next free day she has).

Clearly she enjoyed my company if she already wants to hang out again. I asked what she wanted to do, and she said “I don’t know, I’m good with anything”. This bothered me somewhat, but I’m a big boy, not everyone knows how to be assertive.

When I asked whether she’s doing post-secondary, her answer was the generic “I hated school, so maybe I’ll become a cosmetician”. She agrees with whatever I say and doesn’t have a lot to say about her day, goals, or hobbies. That bothered me more deeply. I’m easygoing, so I spent time reflecting on why this information bothered me.

I have my life together. I’ve got a great part-time job to cover costs, university and my budget balances at the end of the day. I pursue hobbies such as photography, programming, hiking, and cooking. I’m on great terms with my family. I know myself well and what I want in a companion. This girl is wonderful, but it seems she dates as a form of entertainment; escape from her life. I date for a strong equal to share my interesting life with, and I’m not seeing a lot of that in her.

I’m not interested in being a crutch and I can’t save her from a boring life. If there’s a way for her to grow up and not rely on me to fill up her open schedule, I’m open to sharing a life with her. Although she’s my age (19), I don’t think she’s at the point where I can tell her this without grievously wounding her undeveloped ego, especially given how she admires me.

My first relationship (a different girl), about a year ago, ended because both of us had been insecure. Since then, I worked at self-improvement, and I’ve honestly been impressed with my progress. I’m a much more confident and relaxed person than I was.

I know myself well enough to know conversation is important to me. I’d feel lonelier in a relationship than alone if the other person had nothing interesting to talk about, AKA, their own life. I’m looking for a healthy relationship where our worlds don’t revolve around each other, but where we know there’s respite in each other’s company.

How can I kindly tell her that she’s wonderful and brave, but not ready to be the female lead in my story?

Casting a Female Lead

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I’m in some troubled and rapidly freezing waters. I live with two roommates and it’s been a peaceful arrangement so far. I lived with one roommate, A, in my last place, and my other roommate, B, is one of my best friends and it’s our first time living together.

We’re responsible for filling an empty fuel tank for the winter, but didn’t realize this until recently.  The financial stress of filling this tank is being felt mostly by B and me (I’m a full-time grad student and part-time server, B needs to save for a car because of Family Stuff), and A is having trouble relating to us since she is relatively sound financially with her off-the-books job and reduced rent (which we agreed to since she had a smaller room).

Because we meet preliminary qualifications, I applied for state heating assistance, but to complete the application I need a social security card from A. Unfortunately, it has somehow been misplaced. A is incredibly lax about trying to remedy problems that might be much higher up on other people’s lists of Stuff To Get Done (ie, paying bills on time, cancelling missing credit cards, replacing a lost driver’s license). I’ve already told her about needing her to apply for a new card, so the ball is entirely in her court.  B is freaking out though, and it feels like there is literally nothing I can do beyond offering to drive A to the office and sit with her while she applies for a new card to ensure it gets done.

Confronting A, or when she gets stressed about out things, also causes her to shut down and lash out and procrastinate even more. B and I are stressed for many reasons, and A also doesn’t seem to understand why we are so pressed financially. Her proposed solution is to ask her boss for the money (and that’s a Hard No from me). B has been venting to me exclusively and it’s harder to handle and try to be the middleperson when I’m also angry and hurt. Long-term solution here is to not live with A again, but for the short-term what can I do to effectively encourage A and express the importance of how much this Needs To Get Done, as well as smooth things over between all three of us?


It’s getting a little heated, but not the kind of heating we need

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Hello! This is a question that is hopefully less fraught than a few of the other Holiday Questions and I hope will be an easy question for you all to answer.

My partner and I have been living together for over a year and together for much longer than that; it is a thoughtful, committed relationship and I’m very happy. My parents took some time to warm up to him but now like him very much (him wading in (yes, literally) to help at last Thanksgiving’s Sewer Explosion in the Parents’ basement went a long way towards them recognizing how good of a man he really is).

The problem: my family is deeply Catholic (not me) (and in the liberation theology, Nuns on the Bus, Vatican 2 kind of way, which helps). Until my partner and I marry, my parents will not allow us to stay in the same bed. We have no plans of getting married unless there is some extenuating circumstance, and then certainly not in the church.

I haven’t brought it up in the last year or so because 1) I want to respect their beliefs and 2) most of the times we’ve been home, I’ve been sleeping on a couch or with my sister anyway since it’s been for other family events where there’s a full house. But now it’s gone on for a long time, and aforementioned sister yesterday got in a fight with my parents about creating a “boys dorm” and a “girls dorm” for our next family vacation (this also will impact my brother and his girlfriend, who have been together since they were sixteen but also are unmarried). They told her that it’s clearly not an issue since I haven’t brought it up and she’s overreacting. She is not.

Look, I’m not trying to have wild kinky sex under my parents’ roof. I would like for my partner to not have to sleep on the floor (or as happened on other vacations, in a tent outside), and I would like to feel like my parents respect our relationship. How do I broach this topic and make it clear that this does, in fact, bother me, but I’ve thus far respected their wishes — but it is a problem that they don’t seem to respect me or my relationship as responsible, adult, or mature without the parameters of Catholic marriage? Do I even bother? Is this a passive aggressive nightmare waiting to blow up ten years down the road if I don’t say something now?

Help me, Captain Awkward! You’re my only hope!

Grandma’s sleeping in my bed this year anyway so it doesn’t even matter right now

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