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Dear Captain Awkward,

I have a situation that is getting very awkward indeed. In a few months, I will be going on vacation to Tokyo with my best friend. This has been a dream of ours for a long time, so we have a lot of plans. A coworker – with whom I’m friendly, but not very close – heard through the grapevine about my trip and started a conversation about when I was going and what I planned to do.

The week after that, she told me that she was planning a trip on the same dates, and she was so glad to know someone who could ‘show her all the sights’. I was a bit taken aback, but I told her my plans had just included myself and my best friend, and we already have reservations booked for just the two of us for most of the attractions we want to see. She seemed to understand and didn’t mention it again for a while.

However, I later overheard her talking to another coworker about ‘our trip’, and how I had planned everything out for ‘us’ to do. I waited until the other coworker was gone so as not to embarrass her, but this time I told her in no uncertain terms that my plans had not and would not include her. She got upset and said I’d been so enthusiastic about my trip that she’d gotten excited as well, and why was it so difficult for one more person to join us?

Since then, she’s kept talking about ‘our’ trip and what ‘we’ll’ do and all objections I make are completely ignored, even though I’ve stopped being polite and I have told her in front of others that she is in no way involved in my trip. I want to have a great experience with my friend and I absolutely do not want to be stuck playing tour guide to an acquaintance.

Since this is not work-related, I don’t feel like I can bring it up to our managers. I know I can’t stop her from making her vacation plans, even if they coincide with my own, but she already knows the name of my hotel and my rough itinerary from that first conversation, so how can I get it across that my friend and I do not want her with us? I’m concerned that she might have booked at the same hotel or that she’ll show up there, and I don’t want to cause a scene or have to try and avoid her. To my knowledge she’s never done anything like this before, so I’m completely baffled by her behavior. Obviously this problem is a bit different from many of the other letters you get, but I have no idea how to address this situation. Help?

Thank you,
Tokyo Traveller

preferred pronouns she/her

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Hi Captain –

I have a question about keeping yourself sane while trying to get out of a bad situation.

I’m trying to leave my job. Everyone I work with is too. I’m at a very small startup, and the main person in charge is both incredibly demanding and extremely volatile, which makes it virtually impossible to succeed. For a variety of reasons,* I can’t just quit, but I am actively looking and trying as hard as I can to get out.

The problem is that, for me at least, job searching is stressful too, and I’m much better at it when I’m in a good place mentally. Unfortunately, our head honcho makes this really difficult. It’s not just a matter of ignoring or deflecting manipulative or unkind comments; it’s that they’re in touch constantly, with all of us, making it hard to even get the time or space for reflection. They don’t have a lot of family and have devoted the last few years to making the company work, which means that they constantly want engagement and validation (even if they’re berating us), and they won’t stop trying to engage until we cave and give them the answer they’re looking for.

For example: they’ll ask, on a weekend, if a previously-undiscussed deliverable can be done by Monday. If I say it can’t, they’ll ask why we’re not working on the weekend when everyone else is working “like mad.” They’ll then keep messaging me asking what it is that they haven’t explained properly about the opportunities before me, and what they can do differently so that I understand it, and then ask if I’m receiving the messages. If I don’t answer, I’ll receive a talk on Monday asking what it is that can be done to make sure a situation like that, in which we’re unreachable, doesn’t happen in the future. (This is often followed by “I’m tired of arguing with you and want to make this work, but I don’t know what else I can do.”)

So my options boil down to either a) completely acquiesce to all requests, regardless of their merit or any other factors, or b) have a pointless, hour-long conversation that consists mostly of being reprimanded. I should also note that they also want to hang out socially with all of us a lot, and pout if we won’t, which, as you can imagine, also affects the workplace dynamic.

I will be much, much better off if I can stay in this position until I find another one or am in a better financial position to leave. In the meantime, though, I’m so stressed and busy that it’s hard for me to do anything, including look for other jobs. Do you have suggestions for scripts I can use on *myself* here in order to keep myself going? My therapist says just to remind myself constantly that I won’t be here forever and that I am leaving as soon as I can, but the more frustrated I am, the less likely that seems. And I feel like this is a situation that a lot of people get into – cutting toxic people out of your life is necessary, but it’s so complicated.

Sincerely,

Working on Freedom (she/her)

*You can include these reasons if you want, but I left them out for brevity. I’m including them here to indicate that I really have thought about leaving, and really have decided that the best option for the moment is to stay until I get another job. Those reasons are:

– I have < 1 month of rent in my savings account, and am reluctant to borrow from my parents
– My job history has quite a few short stints, mostly due to coincidence and/or bad luck (yearlong grant programs, getting laid off, leaving a part-time job in order to take this one, and, yes, one where I was a bad fit)
– I’m in a weird specialized field where the work I’m doing is actually hugely beneficial to my ability to get a job in the future

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Dear Captain,

Thank you for indulging me by reading my email. I have been a lawyer for the last almost 13 years and been at the firm where I am for the last 5. I was so happy to get this job as I have worked in other firms where my desperation to qualify as a lawyer was ruthlessly exploited in the form of terrible pay, or where I was the only person in the firm doing the area of law I do when I was still in the period where the law required me to be supervised, meaning that I had no-one to discuss cases with and was forbidden from having my own stapler or printer and had to walk down 4 floors to pick up printing, which was massively disruptive. For the first 4 years everything was great. I started the job on the same day as an older lawyer called “Jacob”, and we did the same job ie Big Deal Files With Lots of Money Involved That The Other Side are Fighting and the Court is Involved Which Have Massive Consequences If You Mess Up. Two things happened in 2015 – poor Jacob had a breakdown and messed up a lot of his files and left just after Christmas last year, and also I was ill for a few months with terrible ladies’ problems that caused me to bleed non stop, all over the office, for 4 months. I didn’t take any time off work apart from the day I was actually operated on because I had so many Big Deal Files with deadlines, and if I hadn’t done them they would all have gone to poor Jacob who was already struggling with his own work. So I messed up 2 files by not filing documents in time, because I was distracted by bleeding and/or dazed from meds. Unfortunately, “bleeding all over the office” isn’t a legitimate reason not to file documents in the eyes of the court, I should have made sure someone else did it (although if I’d been well enough to think “this, this and this needs done” rather than “aaaaagh stop bleeding” I would just have done it myself) and the cases got thrown out of court, costing the firm money.

After Jacob had a breakdown and left, I inherited all his files. I am now the only lawyer here who does this type of work (we are a very small firm). For the last 5 months or so, my own mental health has been getting worse and worse. More mistakes are happening, the bosses are reminding me constantly that I am costing the firm money, which makes me more nervous, so more mistakes. I am having multiple panic attacks daily, my hair is falling out, I end up being sick from nerves and I have started cutting myself after over a decade of not doing that. I have been having suicidal ideation since the summer but don’t really want to do it, yet find myself planning how I would. I have seen my doctor and been referred to a psychologist (referral came through last week, one session so far) so I am getting attended to by professionals. My husband and friends think I need to quit and get a new job, or at least have some time off. I don’t know how to get that though – Jacob’s “stress” was met with incredulity (“What does he have to be stressed about? We’re a very lenient firm”) and I can’t even articulate why I am finding everything so difficult that I need time off. My doctor has been trying to sign me off for the last 2 months but I have been fighting him off because I have too much to do. If I wasn’t here nobody else knows how to do this kind of work. The bosses know that my mental health is on a downward slide as I told them in the summer after an embarrassing sobfest in the office, and last week I had a file review where I was found to have not worked on some files and I broke down again, sobbing that I wasn’t well. The bosses squirmed awkwardly at the hysterical woman and said that they were a very lenient firm, and that in other firms I would have been fired after the bleeding disasters. I am worried that they are right and that I am just too useless to be a solicitor. I am also worried that I could make a mistake that causes the firm to be shut down.

One of the bosses, “Adrian” has a tendency to nitpick, and once a mistake is made, goes on and on about it, and will call me in to tell me to do something right away even if I am in the middle of something else. The other two are less inclined to lecture, but I still feel guilty for messing up their business. I am not messing up all my cases, just a tiny proportion, but any mistake on cases like this has massive consequences, in the way that the cases that the bosses and the one other lawyer here deal with don’t.

TL, DR version: I am very depressed and anxious and making mistakes which get me into trouble, then I get more depressed and anxious. Am I unreasonable when the bosses are trying to run a business to want some time off? I already had a week off in September to go away with my husband but the day I came back I was already panicking by 10am. I don’t want to stop being a lawyer, I used to be able to do this job. I don’t hate working here either, it is a nice place to work compared to everywhere else I have been, I just hate that this has spiraled out of control to this point.

Thank you again for reading, sorry so rambling

A once-competent lawyer

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Hi Captain,

Earlier this year, I agreed to do some work for someone. We hashed out that I’d do about X hours/week, and they’d pay me $Y/hour. It was a hobby that I never expected to monetize, so I was really surprised that someone was willing to pay for it. Between my two official jobs and all the other stuff I’ve had going on this year (moving, cutting ties with my abusive parents, my mental health taking a nosedive), I hadn’t even noticed that they didn’t pay me… for months, now that I look back on my records. Add to this that the work, which used to be fun, now feels like an utter chore, and I really don’t want to do this anymore.

I need a script (email or text) to deal with them. Ideally, I’d like to a) maximize my odds of getting paid (I know there’s no guarantee, since we never signed a contract or anything, and luckily I can survive without the money), and b) make it clear that I will no longer be working with them, since this behavior is unacceptable. Any advice? All my attempts at writing something come out rude and profanity-laden.

-Why Does Everyone Feel Entitled to Free Millennial Labor?
(He/him.)

PS – any advice on not feeling foolish and irresponsible for not noticing this sooner?

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Dear Captain,

I’m in my early 30’s. Having spent my 20’s doing the ‘right’ things (college -> law school -> office job), I have now recognised what was clear all along, namely that this is not for me at all, and that maybe that’s okay. I’ve also realised that maybe it’s okay to not be making the maximum amount I possibly could be, and okay to say ‘no thank you’ to the budding career I have zero interest in in favour of pursuing my passions.

Passions, of course, don’t pay very well, certainly not at first and possibly never. If I quit right now, today, I would be living hand to mouth with virtually no safety net. If I hold on for another 22 months, then I would have a very substantial safety net, enough to cushion me for a decade or more to come (I would still need to work to feed myself, but I would be able to absorb a good number of unexpected financial blows before going into crisis mode), plus put me in a better position in old age. There is no in between here.

Herein lies the quandary: I could die in six months’ time, in which case I would rather quit now and take my chances. On the other hand, if I did quit now and then didn’t die shortly afterwards, 2020!Me’s life is likely to be significantly more precarious and uncomfortable than it would be if Present!Me stays for the 22 months. I should add here that I tend to be a lot more productive in the creative area I want to pursue when I feel immediately secure, so this isn’t even just about my own comfort, but potentially impacts the quality of the work I want to do (and of course the point of this whole exercise is to give myself a better chance of producing quality work).

Knowing myself, I will probably do the 22 months. I don’t hate my job, have no reason to expect my imminent demise beyond the fact that it could happen to anyone, and the job comes with a fixed end date at the end of the period, so I’m less likely to fall into the trap of just putting it off and putting it off until it becomes too late. I’m just having a hard time reconciling myself to the ‘what if’ part right now right now. Help please?

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Readers! Especially Readers Who Are Also Writers! Here is a blog you might want to know about:

Longtime Awkwardeer Rose Fox has started an advice site for writers called Story Hospital. Every week Rose answers a question from a writer who’s struggling with a work in progress or with writing in general. The site’s tagline is “Heal your relationship with your writing” and it reads a lot like a relationship advice column, with a balanced mix of writing tips and deeper analysis of what leads writers to feel blocked, anxious, or uncertain about their work. So far the site has covered being your own muse, writing peer-reviewed papers while feeling overwhelmed by academia, patching plot holes in novels, and figuring out when to let go of a script draft that’s just not working out, among many other topics relevant to both fiction and nonfiction writers. The site is supported by Patreon and patrons get cool perks, including inspirational postcards and access to a priority question queue. Rose has been a professional writer, editor, and book reviewer for 20 years and is overflowing with great advice. Take a look at their site, and if you’re having trouble with writing of any kind, ask them a question!

It’s been a long time since we’ve looked into the abyssthe internet’s unfiltered Id… the words that people type into their search engine windows in order to find this place. Good news, Patreon contributors met the first monthly goal, and this will be coming back as a monthly feature. Shall we dance?

1. “Colleagues surprised I got promoted.”

And they point out their surprise? To you? Depending on my comfort level & closeness with the people in question and the likelihood that they’d have the grace to be embarrassed, I might say something like “Thanks for that astounding vote of confidence, Marian!” to help everyone laugh off the moment. I might also call no attention to it and pretend I didn’t notice, based on the fact that sometimes people have weird reactions to things when they first find out about them and do better when their first reaction can be private.

Now, if they keep bringing it up after that first announcement, like, “I was so surprised they promoted you and not Andy…” – it’s time for a wicked smile and “And yet…here we are!” (+ subject change).

2. “Can I ask neighbours not to be on my drive.”

Yes? “Please don’t use my drive, thank you.

3. “My mother died without resolving our strained relationship or saying thank you.”

We all die in the middle of something unfinished.That SUCKS and I’m sorry for the loss of your mom and for the loss of the chance to make things right between you. It sucks to be grieving someone when you’re bouncing back and forth between grief and anger and regret.

I hope you will honor your mother’s memory and your own experiences with your mom (the ones that made you need to keep your distance) someday when some more time has gone by. Write her a letter of all the things you wanted to say to her, but didn’t. Write the letter back to yourself that you wish that she would send you, the one where she says, “Thank you” and “I’m sorry” and “I understand.

Be kind to yourself.

4. “Why would a man tell you he will take you out for coffee once in a while, even after breaking up?”

Maybe this man has some idea that you’ll still be friendly. Only he knows for sure, so before you say yes you might ask him: “Hey, was there something in particular you wanted to talk about over coffee?”

Before you go, ask yourself:

Do you want to go out for coffee?

Do you want to stay in contact, or would you benefit from a clean break?

Do you want to go even if it doesn’t really mean anything special about your future together?

5. “People who care about grad school too much.”

Duuuuuuuude. Seriously. What is it with grad school, being all expensive and intense and competitive and interesting and stuff.

(I have no good answer, sorry. Grad school: It’s absorbing.)

6. “She says, ‘Not now, sorry’ when I want to talk with her.”

My best guess is that she is busy and doesn’t want to talk right now.

Try saying, “Ok, let me know when it’s a good time” and then going and doing something else with your time for a while.

In a good [romance][friendship][artistic collaboration] she’ll come find you when she’s ready.

7. “My brother is an insufferable ass.”

You can’t choose your family. Can you limit the amount of time you spend in his company?

8. “If my boyfriend forces me to change my appearance”

Is this one of those fill-in-the-blank scenarios?

“If my boyfriend forces me to change my appearance, and it is not a matter of life and death because we are on the run from an international spy ring, then I should dump him for being a controlling jerk!”

People who “force” you to change important things about yourself are not on your side, Young Googler. Please love yourself enough to get away from this person.

9. “Why is my boyfriend really aggressive about me wearing makeup?”

The simplest explanation is that he does it because he is a controlling asswipe. See #8. He is literally trying to control your face. 

10. If a family member shuns you, do they ever think of you?

Maybe? Sometimes? Without action on their part, it’s hard to know.

11. “I found my grandmother’s sex toys.”

Yes! GET IT, GRANNY!

My best suggestion is: Put them back where you found them and act the way you’d like Nana to act if she stumbled across your sex toys (i.e. “quiet” & ” discreet”).

12. “‘Sorry I can’t date you’ message.”

I like replacing “can’t” with “don’t want to” or “am not interested,” if you feel safe to do so. “Can’t” implies circumstances beyond your control, like, “I would totally date you, but this tornado just spirited me away to the land of Oz, so I can’t.” That little window of ambiguity can send a persistent lover into a tizzy of looking for ruby slippers that will click you back to Kansas when really you just want them to leave you in this Technicolor world where it’s not the Great Depression. Whereas, “It’s nice of you to ask, but I am not interested in dating you” is clearer and more specific.

13. “Are all bad girls confident?”

Marie Claire’s former pillock-in-chief Rich would have it so. I need a better definition of terms. What is a ‘bad girl,’ exactly?

14. “How many times should I invite myself to stay as a house guest?”

This is my personal house-guesting code as a 42-year-old white American lady with a job. It does not have to be your personal house-guesting code.

With a close friend or family member,

Where I have a good history of reciprocity,

And I trust them to say an honest “no” if it’s not a good time or whatever,

And the dates of my travel are pretty well-defined (nobody likes “sometime” hanging over their head) and short (1 night – a few days);

…I may ask once or twice or every now and again. More likely when I know that the hosts have a guest room and a habit of saying “Please come visit, we have a guest room and we’d love for you to stay with us!,” in which case, they have invited me and “inviting myself” is more about suggesting a specific time. Much less likely when there is no guest room or guest bed and I’d be taking up someone’s main living space. Not at all likely when the prospective hosts are brand-new parents of a baby or enmeshed in other big deal life stuff. Definitely not if a suggestion of staying there is met with any hesitation; one may askIs it okay if I stay in your guest room for a few days?” but one must not try to convince the hosts.

This was all more fungible when I was 25 and used words like “crash” and traveled more internationally and AirBnB did not exist.

15. “How to ask friends not to invite themselves over?”

“Hey, friend, I love your company, but when it comes to my space, can you wait until I invite you over? Thank you.”

16. “I don’t want to be friends with ex-boyfriends.”

You don’t have to be!

17. “A message to write to a friend to tell some one they are of value to you even if they have gone broke.”

“Hello, friend, I know times are really hard right now. I just wanted to say that you are important to me and I’m hoping things get better for you. Can I fix you dinner sometime soon? I’d love to see your face.” 

18. “What is Captain in sex?”

If you’re lucky, there’s a recorder solo.

19. “Should teenage boys have sex toys?”

I’m neither a parent nor a legal expert, but my instincts say, “Why the hell shouldn’t all teenagers have access to information & resources to make themselves feel really really good in their own company?” I wish to hell I had grown up with Scarleteen and a waterproof, adjustable-speed vibrator.

20. “Do therapists want to hear how their former patients are doing?”

People in the helping professions sow a lot of seeds without expecting to see the blossoms, so, I say “yes” if you had a good relationship and the information is conveyed in a medium that doesn’t demand work from them. Think of it the way you’d write to a former teacher you wanted to thank in a short note, like, “Dear Therapist, I just wanted to let you know that things are going better at work thanks to your suggestions for managing my time and anxiety better. I hope all is well with you, thank you again for your help. Sincerely, Your former patient.” If you find yourself generating paragraph upon paragraph of text, maybe make an appointment?

21. “Stop meddling and being a matchmaker!” 

Yeah, knock it off, Emma! 

22. “Me and boyfriend break up because we never have sex.”

Breakups are HARD, even when they are the right thing to do. I hope you are both happier with a little time and distance, and may your next partner(s) be more compatible with you in that way.

23. “Should it bother me that my husband wants me to party with alcohol & cocaine knowing I have seizures and interactions with medications could be harmful?”

I find it useful to replace the word “should” in talks I have with myself. When we’re talking about feelings or big decisions, what “should” happen is not so helpful. The better question is “what IS happening?”

“Should it bother you…”

==>

DOES it bother you? It sounds like it bothers you. (It bothers me!) And, since you are the sole boss of what substances you put in your body, you are the sole decider of what risks are unacceptable for you. “Husband, I don’t want to ‘party’ with you. I don’t want to have a seizure or a bad interaction with my meds. Please stop asking me.”

24. “My roommate leaves the bathroom door open when he goes to the bathroom and showers.”

“Dude, close the door!” (+ open the window!)

 25. How to get your boyfriend to look after himself?

Any answer I give is going to generate an automatic “But it’s more complicated than that!” or “But I love him!” response, and rightly so, but I’m going to talk to my younger right now and let everyone listen in. If it’s not applicable then it’s not applicable.

Hey, Young Jennifer, I’m so sorry, the Time Machine did not get me back here in time to stop you from falling in love with [Hot But Troubled Boy]. I had the dial set for 1990, which is why I have all these catalogues for women’s colleges and a bass guitar in here with me, but I can see that I’m a couple years late.

I know you love Boy. His skin feels like magic and when you touch each other it feels like the microscopic space between you is filled with stardust. He smells like two angels fucking. You can stay up all night talking and fixing the world together. You are unstoppable…except for when he is very stoppable.

Boy has a condition called depression. You have it, too, and you should go and get checked out for that. Where I come from you didn’t figure that out for another 5-7 years, and I can’t help but wonder what would be different for me/us if you knew. Depression doesn’t mean you’re unloveable, it just means that it can take medical help and concentrated effort to manage the condition. When Boy hates himself, and stops going to work or class or washing his clothes or wanting to do anything with you, when he has mood swings and gets dark and mean, when he tells you that he doesn’t deserve you and wants you to go away, and then the next day tells you that he’ll die if you leave him,  it’s at least partly a manifestation of an illness. It’s not your fault, it’s not something you are doing wrong or not doing enough of. What that also means is that you cannot love him out of it. You can’t fix him or fix it for him. He’s got to do it himself.

What I know now that you don’t know is that the time you are spending, tidying his space for him, worrying about him, talking to your friends about what to do about him, trying to coax him to eat or shower or go see a movie with you, wondering what he’s thinking about, making sure you always look pretty when you see him, keeping track of his schedule and his deadlines, processing the stuff he says to you in and out of his mood swings, taking care of him, trying to lay your love and your body down into all his cracks and fill them, time spent biting your tongue not wanting to make him sad or angry…this is time that you will never get back. You are stealing these years from yourself and offering them up to him, to no one’s benefit.

I know, you love him. I know.

And I have unfair knowledge, because I know stuff that you can’t know now, that maybe you wouldn’t have ever learned if you didn’t try and fail at this.

But I’m from the future, and if I could tell you what to do right now I’d tell you to have one conversation with him where you ask him to seek help for his troubles and to start being nicer to you. If he does? Great, maybe you can have that love story you’re so sure this is going to be. If he won’t? Especially the part about being nice to you? Then I’d tell you to bail. It’s too late for the women’s colleges, but it’s not too late for the bass. Take it, find some other awesome women, start a terrible punk band, and use all the painful things he’s said to you as material for lyrics. Hold out for someone who is always kind to you, someone who doesn’t need to be fixed or parented.

P.S. In 1997, when your friend I. offers you a chance to work at her internet startup but you’re going to take the job at the non-profit instead? WORK FOR I, FOOL. She’s gonna sell that thing to Yahoo right before the crash in 2000, and you can donate your millions of dollars to the non-profit.

This is Captain Awkward Dot Com Pledge Drive Week, as you know. Ways to contribute:

  • You can become a patron at Patreon. At the next funding goal, I release an e-book of columns once every year, free to patrons, a few $ to download for non-patrons. When/if we hit $2000/month, the blog goes ad-free. 
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Thank you so much for reading and for your generosity. It really makes a material difference in my life.