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Author Archives: JenniferP

This is another one in a series about difficult parent relationships: A dad who wants to talk on the phone for hours about only the things he wants to talk about and who reminds his daughter, when she tries to set boundaries, that he has nobody else to talk to. It’s about guilt and about how the hardest part of boundary-setting can be a negotiation between us and ourselves. Maybe the key to this negotiation is figuring out the difference between “should” and “want to.”

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I’ve gotten a bunch of letters about family weirdness and estrangement and boundaries (weird, almost like there was a series of events in the last month that forced a lot of family togetherness, can’t think would have caused all these old wounds to re-open at the same time? 😉 ) and I’m going to put up a series of them this week. This one is about the aftermath of cutting ties with a parent and the still-present worry that running into them will be awful.

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Hey Captain Awkward.

I read some of your responses to other writers who had concerns about their partners’ finances, and I feel like this is related but not quite the same.

I’m stressed about my boyfriend’s money management skills and how I can help him without getting myself into a bad financial situation. I also recognize that he’s probably embarrassed on top of being stressed, so I’m trying not to make him feel ashamed. He was raised below the poverty line and when he made it “big” in his industry, he was earning huge salaries, so I think he’s allowed himself to fully enjoy it. Now he’s unemployed but is still living a “huge salary” lifestyle.

About me: I’ve always lived pretty frugally. I’m kind of a prepper in some ways – I buy a lot of dried or bulk foods, and I park nearly a mile away from work and walk every day so I don’t have to buy a $400 annual parking pass, plus I get some exercise which is hard to come by in my 9-5 cubicle lifestyle. My mortgage is manageable, 90% of my furniture is thrifted (thank god eclectic/Boho decor is “in” right now), I pay my bills on time, I have a modest emergency savings, and I have excellent credit — with a little bit of revolving credit card debt. My house is my first home purchase, and in addition to receiving some assistance from my grandparents, I participated in a federally funded first-time home buyer program and saved for years to come up with the down payment. My house isn’t fancy, but I love it because it’s mine goddamnit, and after changing addresses every year for 18 years, I finally get to lay down some roots! I‘ll hit my one-year anniversary of homeownership next week. Yay.

I do not typically seek out partners with tons of money. In fact, I’ve been known to date transient wildlife biologist types who briefly stay in the area to work for six months out of the year, and then squirrel their earnings away to get by the other six months. I just happened to fall in love with my BF who – up until last summer – was successful in his career, made a lot of money as a senior level designer with some recognizable household brands, and was promptly relieved of his duties the same week we met. He felt it was a blessing in disguise because he’s burned out on doing design for a living and wants to pursue his passion of selling rare European cars.

BF was earning a gratuitous salary last year, and while he lived within his means, said means were extravagant and now unsustainable: he owns two houses and has 7 cars (or 8? I actually don’t know anymore). Again, cars are his hobby/passion, as well as his side business, so some of this is to be expected. Two of them are “investment” items that will continue to appreciate in value, two are for driving, and the rest are “projects” that he plans to sell… but as you might imagine, this ties up a lot of capital in non-liquid assets.

BF is hemorrhaging money, but not cash, and is putting a lot of charges onto credit cards. He justifies this by saying that most entrepreneurs fund their businesses through credit. BF also owes his best friend a sizable amount for a recent generous loan which seems to have strained their friendship a little.

Three months ago, BF put his second house, which is in a popular resort town a few hours away from where we both live, on the market. He’s received multiple offers on the second house, but due to complications beyond his control, they continue to fall through, and so it remains on the market. BF was relying on the sale of this second house to kick-start the car business.

His monthly expenses (e.g. mortgages, private school tuition for his two kids, and commercial space for his new business) are over $5k. Not included are utilities, groceries, gasoline, health insurance, pet expenses, or anything else fun/recreational like an occasional meal out or outing to the nearby large city. BF has very little income right now except for infrequent freelance design work which he loathes and the car side hustle. Currently, he sells a car every 4-8 weeks and each sale results in a few thousand dollars. I in believe he’s receiving unemployment, but I’m not sure that he’ll qualify for much longer.

I told him he could sell his primary house and move into mine if he wanted. My mortgage is literally half the size of his, and if he paid HALF of my mortgage he’d still save $2k/month. However, he doesn’t want to sell his primary residence for a lot of (legitimate) reasons, and he wants to keep trying to sell the vacation home that’s been on the market for four months. OK, I get that… But right now, it’s just him and his dog occupying a 3,000 square foot space. He wants me to rent out rooms in my house and move in with him (I would contribute to his mortgage, which would only cover 25% of his monthly payment). I am considering it, but I’m also so happy to finally have a home of my own… it would make me sad to move out of my first home so soon.

I know he’s filed for bankruptcy once before, and he recently said he doesn’t want to do that again (he said it semi-jokingly, so I don’t know how much of a real possibility it is for him). He also told me early on that he thought I’d be a good influence on him as far as spending habits go. These were yellow-orange flags for me at the time. Now, he’s asking me to go with him to a cousin’s wedding on the absolute opposite side of the country in two months. We both have airline miles that will cover the trip, but it’s honestly not how I want to use those miles — the whole reason I got a credit card that gives airline miles is because he suggested I get one so we can travel overseas together this year. I wouldn’t have taken out a second line of credit if I didn’t think we weren’t going to use it for an *international* vacation. Plus, the wedding trip in two months becomes more expensive when you add up the other items that will not be covered: lodging, dining out for five days, hiring a pet sitter for our two dogs, rental car, etc. And I’m also just feeling less and less secure about out future together as the weeks roll by. Like what kind of message would I send to his family by attending this big family event if I’m not sure how into/secure I feel about the relationship by the time the wedding rolls around?

He has also half-joked about how I should have offered to pay for a recent ticket he got because he’s so broke. (He wouldn’t have received the ticket in the first place had he agreed for us to take my car that morning — which gets twice the MPGs — instead of his… but he insisted on taking his car. It apparently didn’t have a front license plate which resulted in a ticket.) The irony is that I almost offered to pay for it as a “sorry you’re broke, happy belated birthday” gift… but after he said that, I thought “NOPE. Nevermind; I don’t owe you shit.”

Let me preface that BF is the closest I’ve found to “my person”, if you get me — our connection, chemistry, and compatibility are mind bending. I’ve dated a lot of people in my day and never felt about them the way I do about him. I want to live with him at some point, get married, and maybe even have a child. How can I communicate my concerns to him without compounding his stress and sounding like a tightwad? (Also… Am I a tightwad? I’m starting to doubt myself and my saving habits…) And how do I support him without getting myself into a bad financial situation of my own? I don’t want to lose my savings, wreck my good credit, or be his cash cow, but I do want to be there for him in a way that empowers, not enables. I can see a future with him… so do I just sit tight through this rough spot and hope it all works out soon, or am I aboard a sinking ship and just don’t have the perspective to see it? Also, is there a way I can get out of attending this wedding?!

Thanks Captain Awkward!

Hello! I am so glad you wrote!

And congratulations on this month’s award for “burying the lede”! I retained the subject line of your email as the subject line of the post because I wanted readers to ride the same “oh, only 7 cars? Or is it 8?” roller coaster I did. 🙂

Screen Shot 2020-01-18 at 4.14.29 PM

Image: A certificate for excellence in “buring the lede in an advice column letter”

You have been so candid and such a good advocate for yourself that it makes my job very easy. My advice is:

  • Do not jeopardize anything about your finances or housing to “help” or “support” a man with 2 houses and 7-8 cars. 
  • Re-examine the idea that it is your job to help him figure out his money & his relationship with money. 

I’ll elaborate but here are some scripts:

  • “I do not want to move out of my house.”
  • “I do not want to move out of my house to make housing payments on a house I don’t own.”
  • “I’d rather save my miles and money for a vacation than go to that wedding, and I can’t afford to do both, so you’ll have to fly solo on that one. I’ll have to meet your family some other time.” 
  • “We approach money really differently, and I do not think it will be good for either my credit score or our relationship if we combine money or housing, especially while you’re still getting your business off the ground.” 
  • “I want to help you through this, but ultimately it’s your money and your decision, so one way I can ‘help’ is by having really clear boundaries especially around financial decisions that affect me.” 

Additionally, scriptwise, be very blunt and specific about money in your dating life. Do not let this flounder in expectations and hints, get in the habit of nailing stuff down like where are we going, what is the anticipated cost, who is paying. When you are offering to pay, make that offer up front: “Can I take you to ____ tonight? Dinner’s on me.”  (This is a good thing to do anytime you are treating a known poor-er person, the anxiety of guessing and mentally running the budget numbers is just awful and fun-destroying). When you are splitting costs or expenses, settle up right away. “The bill is ______, do you want the waiter to split it for us or do you want to pay and I can Venmo (etc.) you my half?”

This may seem unromantic and tedious, and it might bring out some weird shame behaviors and avoidance in him, but do it anyway. If you can’t afford something, say so. “That sounds nice but pricier than I can handle right now, can we save it as a treat for next month and stay in tonight?”  Make this shit matter-of-fact and normal. Make yourselves a couple who can talk frankly about money in mundane, routine ways that doesn’t require big negotiations or emotional processing.

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Dear Captain,

I (34/she/her pronouns) have a new stepfather as of this summer. He has been with my mom off and on for the last 10+ years, and they finally married in July 2019. I think this man is a Garbage Human, but we have to let our parents make their own adult decisions.

A bit of background – my highly narcissistic mom and I have reached a detente after several years of fighting and NC (no contact). She knows what sort of leash she is on, she knows that access to her only granddaughter depends on her good behavior. We mostly get on ok.

SF seems to be of the opinion that he can smack talk my mother’s shopping habits to me when she is not there. I could use some scripts to help deflect him, because while I am very frequently in my first class compartment on the “My Mom is Awful” train, I do not want my stepfather as a seat mate.

Help?
This Train Has No More Room

Hello This Train Has No More Room:

Oh yeah, shut it down.

Your stepdad humorously venting or having “Hey, is this normal, or…?” or “Here’s what’s going on with me” conversations with a close friend or other trusted member of his personal council of advisors is within bounds, but you don’t have to join that advisory board.

He’s either trying to bond (badly), assuming y’all are much closer than you are, or sending out a triangulation advance scouting team to test things like “Will LW not repeat mean stuff to her Mom?” and “But will she repeat the stuff I strategically want her to, so it comes from her and not me?” but it doesn’t really matter what he’s after, you can still opt right out. He could be like “I’m just making conversation, your mom is what we have in common” and you could still decide “Nope!” He doesn’t have to be aware of the history of how much effort it’s costing you to even be around him and your mom for you to decide “I’d prefer not to,” and you don’t have to explain yourself.

You don’t have to explain yourself, but silence will only encourage him to continue, so the next time he tries this you’re going to have to say something. Possible scripts:

  • “Wow, what a weird thing to say to me about my mom.” + redirect your attention away from that topic. 
  • “Sounds like a good one to talk about with Mom, a therapist, and…nope, actually just those two.” + redirect your attention.
  • “I thought we covered this: Don’t say anything to me about my Mom or anyone in my family that you wouldn’t say when they’re in the room.” Then, redirect your attention.
  • “‘Ladies be shopping’? Whoa, save it for the comedy club!” There is a decent chance he is one of the legions of shame-proof straight, cisgender men who are convinced they could do stand-up professionally despite never once having made a person who wasn’t dependent on them for a salary, lunch tip, or lucrative sales contract authentically laugh. If he comes back with “Ha, I’ve always known I could do stand-up!” try “Sure. Pose as a time traveler from 1983, and let me know when it is so I can not be there.” Then redirect attention, etc.
  • Use your “Yikes.” “Wow.” “What.” “Nope!” “But jokes are funny.” as necessary and then redirect your attention.
  • You could ask him, “When you say mean stuff about my mom what is the reaction you are hoping for?” but do you actually want to know? If you think he’s looking for an excuse to expound, don’t use this one.

Redirecting your attention could mean:

  • Being very terse, flat, and boring in your reactions.
  • Changing the subject.
  • Leaving the room. Doesn’t have to be a dramatic exit to make a point, wandering away because you need a glass of water or to make a phone call or use the rest room does the job.
  • Ending a phone call, social media back-and-forth, or text conversation. Anything from “Ok, gotta go” to not replying to selective replying to using “mute” and other filters to best serve you.
  • Starting up a pleasant side conversation with someone else in the room.
  • If you are a person who tends to space out, harness it. Were we still talking about that thing? Who knows? You kinda spaced out there for a second. (Might as well make it work for us for once).
  • “Rudely” disappearing into your phone. Sometimes the people in the internet are much nicer than the ones we’re related to, sometimes “Oh, sorry, I’m getting distracted by this work message, I need to handle it, if you’ll excuse me” is what gets you out of the moment.
  • Over time, limiting contact with people who routinely stress you out. You know all about that, Letter Writer!

I know I’ve recommended all the above actions individually a whole bunch, but I started thinking of them as a unit to be filed under “redirecting your attention” during the holiday posts, some of the “reasons are for reasonable people” and “why do we spend so much time and energy on the worst people?” discussions, and definitely as part of a “do less” approach to fraught relationships. We spend so much time and energy worrying about communicating with people who don’t give a single shit about our feelings or our comfort. Can “do even less!” in 2020 be about changing that equation?

For example, politely changing the subject is useful, I’m a fan, I like to let people save face and de-escalate situations when I can. But how long do we have to knowingly walk into certain rooms with a list of safe, innocuous topics that we extensively strategized about beforehand, and then cheerfully toss them out like a gym teacher distributing tennis balls at the beginning of class and pretend this is normal, neutral thing to have to do?

Do we have to pull every mean and annoying person we know aside and earnestly and patiently discuss our boundaries, or spend all family gatherings navigating patiently around the people we don’t like and didn’t come to see? Or can we say a quick “hello” for routine politeness’ sake and because it would take more effort to freeze them out, and then go talk to the people we actually like?

When someone says something out of line, can it be enough to say “Jeez Louise! What a weird thing to say” and then skip right to “Oh hey, there’s Louise, I’m going to bring her a glass of water” and keep it moving right out of that conversation? Not as a way to “reinforce the boundary” or convince anybody of anything, more like, that’s done, now I’m reclaiming my attention and re-directing it where I want it to go, somebody else can change the subject for a change.

‘Cause sometimes what the person who is behaving badly wants most is more of your attention, by any means necessary, and if they don’t get the initial high-five or commiseration or invitation to expound they hoped for, they’re willing to be loud and wrong if it means they can suck you into a longer conversation where you discuss the subject by which they mean they get to talk more about it. 

If your stepdad is one of these people, being told “no” is just fine, he’ll promise he won’t say mean things about your mom anymore, but that doesn’t mean he’s gonna shut up, not when he’s just gotten started, can he interest you in a long, involved back-and-forth about why he is the Normal, Cool, Reasonable One Who Is Trying Here and you are the Touchy, Humorless One Who Can’t Take A Joke, Just Like Your Mom, now with extra bad faith? It’s entirely possible that the more you try to talk about stuff you don’t want him to share, the more opportunities he has to try to “discuss” your mom with you, which…is exactly what you don’t want.

Emotional sea-lioning is still sea-lioning, someone whose opinions you don’t care about being “very concerned” (or whatever) and wanting to “get to the bottom of things” or “work on our relationship” doesn’t mean you have to play along. “Ok, stop doing the behavior and the relationship will be fine” is your way out of that one. Resist the pressure and the urge to play the “what if” game. What if your mom’s shopping is excessive and causing financial problems or making him think dementia is happening and he’s worried about her? ‘kay, maybe, then he should talk to someone who is close to your mom (clearly not you) and someone who didn’t just get finished telling him “Hey don’t tell me stuff like that about my mom” i.e. Not You. What if your mom is mean to him and he’s regretting the marriage? He should talk to someone who likes him (Not You, again!), someone who cares about their marriage (this role will be played by…Not You!). Does he want someone to talk with about aging, wills, elder care, and the like? Simple, he can ask people he knows for recs or type those words into Google and click any results that do not contain your name. Is he trying to loop you in because that’s what would happen in other families? Cool, cool, somewhat understandable, but he’s known you for 10 years and he knows you don’t have that relationship. Does he think he can repair the relationship you and your parent have with each other? What an unusual hobby, he should get that looked at by (you guessed it) Someone Who Is Not You. Is your mom perhaps deputizing him to talk to you on her behalf? She knows where that game ends by now, it ends with You, Not talking to Her for extended periods of time. It doesn’t matter why. Hold fast to the safe, happy life you have created and don’t let either of these people make their problems into your problems. 

Letter Writer you are smart and realistic, you obviously have some hard-won boundary-defending skills, and correctly, you don’t want to change this dude, you just want to avoid this dude slightly more and slightly more skillfully than you already avoid him. So when your stepdad says weird stuff about your mom to you, tell him to stop in the quickest and most efficient way possible and then redirect your attention. Don’t worry about getting it perfect, if your stepdad thinks you don’t like him much or that you are unreceptive to his confidences, those things are true, so…:shrug emoji:?  If someone you don’t like, whom you see incredibly rarely, under highly-controlled circumstances decides you’re not exactly his cup of tea, I think you’ll manage to carry on somehow. 😉 If the train called “Mom is Terrible” and the train called “Both Of You Are Terrible” leave the same station at the same time, they will be necessarily be on parallel tracks that can’t meet without causing a serious accident. It doesn’t matter if they are headed in the same direction part of the way, or how long it takes to get where they’re going, or if they double back and cross each other’s paths sometimes, this isn’t the fucking SAT and you don’t have to show your work.

Let us close with a video montage. Is Miranda Priestley (antagonist of The Devil Wears Prada) a paragon of warmth and human kindness? No.

Is Miranda Priestley going to get three visits from three spirits one Christmas Eve to examine her past, present, and future? No, every rich mean person doesn’t get issued a personal redemption psychopomp, but I would watch the hell out of that movie, twice if there were Muppets.

Is Miranda Priestley extremely good at getting people to stop talking when she’s done listening and might you want to harness some of that “I said what I meant and I mean what I said kthxbye” energy when you talk to your stepdad? Oh yes.

 

I’m writing this from an inexpensive AirBnB not far from Awkward Apartment, where I took a few days to be in a blank slate, away from cats and laundry piles and human conversation, so I could sit in quiet and solitude and think about how to get my ambitious projects off the ground this year. I wasn’t going to blog but this question jumped out at me and I’d like to shoot it like a fiery arrow across the horizon for me and my fellow creatives who are trying to figure out how to go from the hard drive or the manuscript drawer to the world. Here is my 2020 Note to Self:

NO MORE SHITTY LIFE-HACKS OR PROCRASTINATORY MINUTIA AROUND FORMULATING “THE PERFECT MORNING ROUTINE FOR BEING AN ARTIST” OR WHATEVER

GET TOGETHER WITH OTHER PEOPLE WHO LIKE YOUR STUFF

AND MAKE YOUR STUFF

AND SEND IT OUT INTO THE WORLD

AND THEN DO IT AGAIN

THAT’S IT, THAT’S YOUR ONLY JOB

STAY ALIVE AND MAKE ART

And now, the first letter of the year:

My dear Captain,

I have been reading your blog for many years, since the early days. It’s been so exciting watching you grow! I’ve often been able to find something in the archives applicable to my general situation, or the forums have been a help. Now, though, I’m in a fix, and I don’t know what to do or whom to ask for help, and I’m hoping you might be able to provide some guidance. I’m desperately hoping you will, in fact. I feel like I’m about to have a baby and I’m looking for a hospital.

I’ve written a drag rock opera of Bible stories about the bad women in the Bible, whores, killers, and evil queens. It came out really good. Really good. The issue is that I did it as a self-taught nobody by myself in my bedroom, and now it’s just sitting here in my lap with nowhere to go. I have no money or connections, and no way to produce it. We (husband and two young daughters) moved to a very large city a couple of years ago, and while I would never have had the scope to fully form and finish my project as it is if we hadn’t come here, I’ve never really adapted to big city life. I’ve had trouble connecting with collaborators. They way people operate here just isn’t what I’m used to. People are just so insular.

While everyone I’ve played my material for loves it, I haven’t been able to connect with anyone who can make the whole project happen. The couple of people (one drag queen and one belly dancer) who I’ve connected with seemed really excited about working with me, but they wanted to do one or two pieces at a time in a small venue. No. Would you agree to viewings of only two minutes of one of your films?

This is a piece. It’s meant to be performed as one big thing, from one end to the other. The songs form a progression and tell a story about oppression of women and queer people. It’s a whole thing! It’s not just music.

This wouldn’t be a *problem* (hence this email) if I hadn’t lost my job in September. I’ve spent my entire marriage of 17 years supporting and following my husband as he got his career going, really never having any focus of my own. I had a short-lived local career as a singer-songwriter in my youth that fizzled as I never really liked that kind of music that much, or the kind of work it entailed going it alone. I always wanted to do something different as an artist. I piddled around in a series of jobs that didn’t really mean that much to me, spent an ill-fated year in law school, stayed at home with the kids for a few years, worked as a paralegal…and when I found myself looking for work, it felt so demoralizing to be digging through job listings when I have a masterpiece sitting in my lap. But what do I do with it?

I have some friends who advise me to get on Twitter and reach out to people, but I am a ghost on the internet and have zero social media presence. When I created a profile, it didn’t go well, and I’m worried my clumsiness will only sabotage me, so I hesitate to start contacting people. And let’s say I get it sorted out and do contact people, what direction do I take that? Social media just gives me all kinds of anxiety, way more than my regular social anxiety. I don’t even want to be out there under my own name. I have kids and I spend most nights at home, but even if I were to go out and start “pounding the pavement,” I don’t know where to go. Most drag shows start when my eyes are getting heavy these days. Do I start with drag shows? Or am I looking for theater? I have no idea anymore. I feel like this strange hermit living in a cave with a golden egg, polishing it and loving it, but having nowhere to take it.

I had a plan before I lost my job to use my Christmas bonus to buy equipment to produce tracks to perform to, but even the first step went bust before I could take it.

The material is ready. I’m ready. I feel like I’m about to have this baby. What do I do?

Please help.

Thank you

Bout to Pop (she/her)

Dear ‘Bout to Pop:

Your musical sounds AMAZING and I want it IN MY EYES AND EARS right NOW.

To get it there you are going to have to:

1. Copyright your stuff. It protects you legally, it forces you to record/document it in some kind of tangible way and send it out of your house. This is a good step for someone who is where you are.

2. Make a monthly budget called “Get my show made.” If it’s a small budget right now, that’s okay, but you need a line item in your budget & your family’s budget for this. This is a big deal. This is you. This is your work.

3. Make a sacred weekly time on your schedule called “Get my show made.” During this time, you are not Mommy or Honey, you don’t give a fuck what’s for dinner or whose turn it is to pick the music in the car today. You’re getting your show made. You are working. Treat it as seriously as any day job.

4. See shows and meet people. What theater company where you live does the best/most musicals? Their directors and producers might salivate to get their hands on new work. Would they workshop something for you – stage/light/costume design a few numbers? Howabout producers in your local drag scene? Could you jointly crowdfund a fringe festival pilot? Time to hire a babysitter and drink caffeine after 3:00 pm, ’cause once a month you have a date with THE STAGE.

5. CALL THOSE PEOPLE WHO WANTED TO DO A COUPLE SONGS A WHILE BACK, APOLOGIZE, AND LET THEM PERFORM SOME SONGS.

FYI this was the part of your letter that made me yell “NO!” and “OH MY GOD!” and HAVE TO answer it.

I will stop yelling but I needed to BIG FONT yell for a second. I understand wanting to be protective of work, but I would absolutely let someone screen a single episode from a web series or a short film or read the first 10 pages of a feature script before committing to the whole thing. Your work is “too big” right now, so make it smaller!

I believe you that your piece is great and best viewed in full, but a) workshopping parts of a larger show is a standard part of the creative process (Have you ever seen your work performed? Have you ever seen any of this piece performed with lights and costumes and an audience? You will learn so much omg do it just do it please just do it.) b) “Get a short digestible chunk that people can love in front of them so they’ll ask you for the whole piece” is one of the bedrocks of getting content seen by pros in the entertainment industry. If you continue to insist that people who don’t know you or your work have a choice between “all” or “nothing,” you may get lucky someday but you’re going to encounter a lot of “nothing, sorry” on the way.

Staged readings are a thing. Workshops are a thing. Showcases are a thing. “Viral” videos of works in progress are a thing. Make them your thing. You did the hard, lonely part of having an original idea and putting it on a page. To get it on a stage, you need other people. Their enthusiasm and love for your work is not a threat to you, it is the engine that will make it real. A short version or excerpt is not a threat to the whole, it is the “trailer” that builds anticipation and excitement and shows off what you can do. Big productions evolve out of small moments, ideas, sketches.

Furthermore, “This is a show that started as a few songs performed here and there in drag clubs” is the best damn origin story imaginable, not something that will ruin the eventual “Julie Taymor presents…” on the fancy marquee. Your idea about a show about the Bible’s bad girls intrigued me, the prospect of that show originating with and piloted by drag performers completely SOLD me. Collaborate with and harness and trust the enthusiasm of these people who love the work when you are a “nobody.” What you’re telling me in your letter is that your work is great and you’ve already made some strangers love what you do and want to be a part of it. THAT is a success and THAT IS where this starts. These people who fell in love first will invest their time and love now and make it happen with you and for you through the whole life of this project.

ACCEPT THEIR GIFTS. And take them with you when you “make it.” Opening night on Broadway I want to see you give an interview like, “Me & a bunch of drag performers started this together when they took a chance on me and performed some of my songs in clubs and laundromats and wherever people would listen, now we’re all on Broadway together, singing about the Bible’s Baddest Bitches, because they believed and made it possible.”

6. Hire/recruit the best audio & video people you can to document any and all performances, have them put together a polished cut of each song and a video of the whole showcase. I put audio first for a reason – if you can only afford 1 pro and 1 student/talented newbie helping out, make the pro the audio person. Make a website with a synopsis, photos, all your information before you push the videos online. When this hits you want people to be able to find you easily.

7. Figure out this social media thing so that those songs get seen and heard and loved and sung along to. Lots of awkward, shy people are on social media. Here’s a starting point: Friends-of-blog Julie & Jessica of King Is A Fink wrote a book called Social Media Charm School for social media neophytes who are trying to harness social media specifically to network and promote and make creative projects (in their case, films). There is an older, pre-social media resource about film-funding (movies are expensive and also more my wheelhouse than theater, apologies) but I really like Shaking The Money Tree: The Art of Getting Grants and Donations for Film and Video by Morrie Warshawski. He has lots of advice about raising money through overlooked and unexpected ways but probably the most valuable advice is about crafting your pitch and using your passion and skill in how you tell the story to connect with people who might give you money or want to work with you. You are the expert on you, you are the expert on your story, you can translate that passion even if you are nervous or shy. It’s okay to be a beginner at “Show Business.” Everyone in show business started as one.

Austin Kleon’s Steal Like An Artist and Show Your Work are both valuable and inform the ways I first approached social media for promoting and networking. Using Twitter as an example, the people who do what you do the way you want to do it are on Twitter. You could follow them and listen to them and get to know them. Fellow aspiring goddesses of musical theater are on Twitter. You could follow them and listen to them. You don’t have to say a thing for a while, never mind crafting and pushing the perfect pitch for your project. Just listen. Who inspires you? Who draws you in? Who makes you feel encouraged and excited? Where are they submitting and promoting their work? Those are the seeds of community and fellowship, interacting like a friendly human with other friendly humans who are doing the same work you are, cheerleading each other on. [Beeteedubs Chicago, I have a 60-90 min ‘sustainable, positive social media for indie creators’ talk/workshop I will happily bring to your school or organization, lmk if having a person who hates the term ‘personal branding’ and who found ‘selling Girl Scout Cookies, a thing people love and look forward to every year’ stressful but somehow makes a whole entire living by engaging with audiences online would be useful to you or your students/colleagues/members].

I repeat: Leverage the community you already have (beginning with the people who wanted to put on a short version of the piece), follow and listen to people who inspire you, and get going.

8. Research how new musicals get made. I don’t know how they get made and can’t tell you, that’s your research to do. Hadestown started with a concept album and a small performance. At least one reader submitted their amazing-sounding piece to a contest a producer runs every year. Seed and Spark (where the above-mentioned Julie worked for a while before getting her MBA in saving the world) is a good place to start researching crowdfunding options. Where you live, what theater companies routinely present new work? What fellowships, grants, mentorships, panels, etc. for new playwrights and composers exist? Who routinely directs and produces musical theater where you live? Meet them. And RESEARCH.

9. If you must get a day job, get one where you have a regular schedule, the lowest-intensity-to-highest-money ratio, steady Internet access, and a printer. Last time I had an office job with any regularity, I got my work done in about four hours every day and I also had at least four hours a day where I was trapped at my desk and had to “look busy” but really had nothing to do and that’s part of how I became a writer. Dress well, show up 5 min early every day, and do your paid work with so much competence and integrity and efficiency that nobody will notice when you have 20 browser tabs open and 19 of them are “fringe festival submissions” and “artist residencies for emerging playwrights.” You’ve got to put food on your table somehow and that might be the somehow until this thing breaks.

10. When you get discouraged or depressed, consider “Cats.” 

“Cats” is a real thing in the world. It was ridiculous poems. Then it was a ridiculous show. Now it is, for some reason, a ridiculous movie. If “Cats” can do it, YOU CAN FUCKING DO IT. Approach your creative endeavors with the audacity of every single person who thought “Yes, ‘Cats’ is a thing we will make with our time.” The next time I see the words “worryingly erotic” I want them to be about you and your show.

Let us know when there is video/audio to share so I can smash that “retweet” button, we at Awkward Dot Com Enterprises are rooting for you. ❤

Thank you all for the kind words and end-of-year donations and patronage that have flowed in over the last week or so. I’ve been traveling and kind of made a point about not touching my laptop for a week or so, but I read everything and I’m very grateful. ❤

Everyone’s doing decade-retrospectives and my brain is melting at the thought of it. Ten years ago, I was still technically a grad student/adjunct teacher, I lived with roommates, I’d just finished my very last student film, Captain Awkward Dot Com didn’t launch until January 2011, and I didn’t meet Mr. Awkward until 2012.

But let’s do a 2019 round-up, yes? Here were the most-viewed/shared/discussed posts from the site in 2019:

First, a timely seasonal carryover from the very end of 2018,  “#1162: Is there room to compromise when it comes to alcohol and driving? (Answer: Why not set the default at “Don’t drink and drive”? I made a chart and everything.)

Next: #1215: ” ‘So…about your private reproductive decisions’ and other ‘small’ talk.” 

Let’s please stop asking people about their intense private life stuff out of passing curiosity, the idea of politeness, or because we think we’re entitled to know. When people have big news about babies, THEY’LL TELL U.

While the rest of the world catches up, this post has lots of strategies for answering (and deflecting/de-escalating) potentially fraught “small-talk” questions that can unknowingly hit real sore spots.

P.S. Letter Writer #1228 you’ve been in my thoughts and the offer to fight your family in real life if necessary is still incredibly open.

Third, #1219: “My friend’s boyfriend keeps ‘negging’ me.” 

This post has THREE HUNDRED AND EIGHTY ONE comments strategizing about whether it’s okay to tell a serially annoying dude “Look, could you stop?” and is often re-shared/cited for mention of “Schrödinger’s Autist,” a theoretical construct who only comes out in Internet discussions of cis men behaving badly toward women as a way to pre-excuse bad behavior (and has nothing to do with actual autism).

Fourth-most viewed is #1186: “How do I restore trust in my relationship?

Like the faux rank of “Captain” Awkward, “The Marie Kondo of Breakups” is a self-assigned comedy title because it’s one of my life’s missions to tell my younger self young people, especially young women, that a partner who keeps letting you down and leaving you wondering in the early stages of a relationship is probably not going to change for the better, and there’s nothing you can do to “love somebody more” into being who you need them to be.

It’s okay to want love, to risk, to try to make things work, but working at somebody who isn’t doing any work to be a good partner to you is a lonely and disappointing bet.

Fifth, #1218: “Irritability and constant criticism in a marriage. The post and comments are a good roundup of previous discussions of verbal abuse and safely extricating oneself from a draining and damaging partnership.

Good “Could this be abuse?” guideline: When someone who is supposed to love you is constantly mean and you start asking yourself “what’s wrong with me that’s making this person be so mean, how can I fix myself?” it might be time to visit LoveIsRespect.org from a private browsing window and start making plans.

Sixth, #1198: “How do I deal with work burnout and make my partner* happy?” (*My partner = my boss, who is *a* partner in the law firm where I work)

Notable for link to description of “insecure overachievers”and how capitalism hijacks anxieties and perfectionism in search of star performers, not caring who burns out along the way or how unsustainable and unhealthy the culture can get.

VERY GOOD NEWS: This Letter Writer sent me an update and is doing MUCH, MUCH, MUCH BETTER. ❤

Seventh, #1197: “He broke up with me but hasn’t moved out yet. How do I not ruin our last chance to make this work?” 

I had the worst time moving on after breakups (rejection sensitive dysphoria, yaaaaaaaay) and learning how to let people go was one of the hardest and best lessons I ever learned. I’m proud of this heartbreak omnibus and hope it can make a difference to others. There are enough ballrooms in you, Letter Writer, and I hope you are in much better straits now.

Eighth, #1194: “I’m moving in with my girlfriend and now my homophobic parents want to disown me. One of a series of posts on family estrangement and how to close doors to protect yourself and leave some open in hope of better things. “Forever is a long time, Sally.” Letter Writer, your parents don’t deserve you and I hope your new home with your girlfriend is a cozy and happy one that is everything you want it to be.

Ninth, #1233: “Is it ever safe to take a parent off a low-information diet?” 

People have choices about how they treat you, and relationships don’t get messed up overnight or for no reason, so when a parent wants you to have a “closer” relationship, does that obligate you to try to repair things in some way? Can they acknowledge why distance made sense at the time?

Probably one of the most personal posts I’ve made on the site, this brought up lots of stuff for me and was very much on my mind during holiday visits with my folks. When people talk about the past, my mom says “I don’t remember that” a lot ( A LOT) in a sharp, pointed way that clearly means “So, obviously it didn’t happen.” She’s telling the truth (she doesn’t remember) but it doesn’t mean that it didn’t happen or that my memories are lies. I still don’t know how to ever ethically tell our story or tell her about my writing here, but I know our story lies at the heart of many of the things I write here.

In tenth place, several posts around the topic of “WEDDINGS, WHY ARE THEY SO WEIRD?” came in within 100 page views of each other so I’m re-sharing them all:

  • It’s Mother-Effing Wedding Season Again So Let’s Chat. Your wedding doesn’t exist to fix you, your family, your friendships, your partnership, your body. It does not have to be your sole creative act that communicates your exact social class and crafting ability.
  • #1223: “Feminist Etiquette Wedding Help”. Your wedding doesn’t exist to fix you, your family, your relationship, your body, or the world. It’s a party so try to throw a good one that makes you happy and invites your guests in to what you want vs. trying to argue with each of them about why you’re allowed to want what you want. “Oh thanks, but we’re all set!” is a very useful phrase.
  • #1188: “Grief and empty chairs at the wedding feast.Maybe the idea of ghosts first sprang from the divided vision of grieving people, the way we can both see the party as it’s happening and see the echoes of what the party should be like, our longing giving shape and color to the empty spaces where our loves should be.”
  • #1189: “Fox News, Immigrant Family, and the F**ing Wedding Invite List.Probably the Uncle could have behaved himself for one day, but this thing where we tiptoe around bigots and keep negotiating with non-bigots for “more tolerance” toward bigots has gotta stop. We can work on tolerating/convincing/courting them once we’ve out-organized and out-voted them, let people who aren’t their direct targets run interference for a change.

I should also highlight the awesome series of guest posts from Lenée aka dopegirlfresh aka the GOAT who filled in for me during surgery in the spring. I plan to have her back in 2020, as well as some other exciting guests (Rae McDaniel has volunteered to peek into the inbox to answer questions about gender, we’re just trying to get a meeting on the calendar to figure out the logistics).

The blog motto for 2019 was “Quit working so hard on relationships that aren’t working for you” and I’m still ruminating on 2020’s. How do people feel about “Do even less work than that and see how you feel?”

Love and good New Year wishes to all of you in Awkwardland, comments are open.

Got an update for us (never an obligation, but we love to read them)?

Is there a post from the past year that you found especially useful?

Did you kick ass at setting a difficult boundary this year?

Did you decide to put in “less work” with a thorny relationship? What happened?

Ahoy Captain,

This past year I (31/F) finally received a diagnosis for what I’ve been struggling with for over half my life. I have Complex PTSD/PTSD (I’ll spare you the differences and overlaps) (Ed. Note: No worries! I, Jennifer, will link people to a basic explainer.) Encouraged by my therapist I shared the PTSD with my parents. The main reason being because, with the enthusiastic support of said therapist, I am pursuing a service dog (SD).

Being able to acknowledge that yes, I have experienced multiple traumas and that I deserve to seek help and healing in a way that’s actually beneficial has been huge for me. I am very fortunate that my dog turned out to be an excellent candidate and I am owner training with the help of a professional service dog (SD) trainer. For the first time in forever, I can even sometimes think positively about the future!

The problem is that my feelings of being valid and deserving of help are new and fragile. My mother is extremely dismissive about my having PTSD, deciding to go the SD route, and the legitimacy of my dog being a service dog in training (SDiT). It often gets to the point of being triggering. And when I tell her she’s being hurtful she says she loves me, has good intentions, and somehow I end up apologizing for getting upset.

In the past I had her/the family on a very lean information diet, particularly when it comes to mental health stuff. I am worried about introducing my dog as my SDiT and it making the family feel as entitled to information and judgement as my mom. They mostly follow her lead when it comes to me. Although there have been times when my dad will privately admit mom is super critical of and often cruel to me, he has no intentions of intervening.

We live in different states so Holidays mean my siblings and I return to my parents’ house for several days. If it was just a dinner, I might be able to get through it, but I doubt I can last days in close quarters without utilizing my SDiT and I’d prefer not to lie since the truth will come out anyway.

Do you have any scripts for navigating what is essentially a medical treatment plan they don’t/won’t agree with? Tips on how to introduce my dog as my SDiT and have that be respected?

Signed,

Letting the Service Dog out of the Bag

Hello there! Captain Awkward here with a beta-read and practical service-dog suggestions from The Goat Lady. I hope we’re reaching you while there is still time to cancel or radically alter your plans for this upcoming trip to see your folks.

Because that’s my practical advice: Strongly consider cancelling the trip and probably DON’T talk more in detail about your diagnosis or treatment with your mom right this second if you don’t think it will be safe or productive. More words/context/recommendations after the jump.

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