Dearest Captain,

I’ve been dating a person for almost 3 months, and he is terrific and lovely. Sexy stuff is also ding ding ding jackpot!!!. I’m at the point where I would like to have a low-stress check-in about how we’re both feeling regarding exclusivity and commitment. I know we’re both currently not seeing anyone else. My general impression is that he’s interested in a relationship, but ‘impressions’ are not hard evidence and I just want to address it explicitly without my inner FEELINGS-VORTEX getting in the way.

I’m really struggling to find the right words to initiate this conversation, because everything that pops into my head has strong overtones of “PLEASE LOVE ME FOREVER” and “I’m putting all my hopes and dreams on you despite only having known you for 10 weeks or so”… and those are NOT the kinds of conversations I want to have. They’re definitely not representative of how I actually feel – it’s just that my anxious-attachment mechanism kicks into overdrive at the very thought of addressing it and everything starts to feel like much higher stakes than it really is.

I did some googling on “How to have a DTR conversation” or similar, and Captain, there is a universe of terrible advice out there. Of course, much of it is geared towards straight women, and either implies or outright says things like “Don’t be too pushy. Men don’t like to be rushed. Let him do the chasing.” DON’T STARTLE THE WILD MALE HUMAN. There’s a heck of a lot of cultural messaging to the effect that [in a heterosexual relationship] it is a woman’s role to push for commitment and that men dread this conversation, which makes me both extra nervous about it and also kind of resentful. I would like to be able to leave those feelings at the door when I bring it up, but I’m so lost for the right words to use that I just end up getting even more anxious, and then I don’t bring it up at all because I want to be coming from a place of curiosity and confidence, not from a place of fear.

I’m sure about this guy. He’s kind and responsible and we laugh together a lot and we are hella attracted to each other. I’ve felt a whole bunch of YES about him since we first met, and know that I know him a little better I feel totally sure that I want a committed relationship with him. It’s frustrating and embarrassing for me that I feel so lost as to how to bring this up. I know there’s no one-size-fits-all approach, but do you have any good scripts for having this kind of conversation? I think you’d be doing the world a great service by putting out a few (non-gendered) ways to check in with someone you’re dating about your hopes and feelings about the relationship.

Many thanks for all you do,

Looking For Words
(she/her/hers)

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Dear Captain,

I am transgender (he/him pronouns), and came out to my immediate family last year. I have not come out to my extended family because – well, I don’t consider it their business! In my mind it would be like telling loosely connected acquaintances.

The issue is this: my younger brother is getting married at the end of this year. I’m very proud and want this to go perfectly. But, it’s likely that a fair number of the family will be present. I’m not part of the wedding party but by being family I am going to be alongside the main feature. I wouldn’t pretend to be [birth gender], but my physical appearance is changing and it’s unlikely that I could, anyway. (And I’m really glad that I’ll be able to look more like me in photos that will be around for years to come.)

I haven’t spoken to most of the extended family for several years. Aside from their aggressive take on their religious beliefs, they are rude about physical appearance, unkind about hobbies, and subscribe to very gross politics. There’s practically no pleasant conversation, and if I interact with them I usually find myself wanting to argue, so I Christmas with friends, avoid other family events, and no one has ever rang me up to say they missed me.

My immediate family are supportive – to an extent. I don’t want to ask my younger brother to help handle the family, because he’s got a wedding to care about. My older brother will probably be happy to defend me but I don’t want to the potential for volatile conversation (we both have a fight-first kind of attitude). My parents barely support me to my face, but have acknowledged that I’m an adult and will do my own thing. Primarily they are concerned about appearances, and worried about being judged for their parenting, and concerned about how comfortable the extended family will be.

Because it is my brother’s wedding, beyond family the people will belong to his close-knit social circle, and it’s unlikely that I’ll have a friend I can latch on to. The engagement party had a lot of people in a small space and I managed to avoid the family there. When it comes to the actual wedding, I’m not sure I’ll be able to manage the same.

I’d love some tips on coming out to people you don’t care about and don’t interact with, and coming out to people who are very set in their ways, and ideas on how to quietly inform people who are wondering where [deadnamed me] is, or shutting down unpleasant conversations in a wedding environment. I don’t want my gender to overshadow or interfere with my brother’s wedding.

Thanks

Hello and thanks for your question. I think this answer will cover:

  1. Ways to spread the word ahead of time.
  2. Ways to make the event itself maximally safe and comfortable for you.

In your younger brother’s shoes, I would 100% want to be “bothered” by this if it was causing you anxiety, and there would be no way that your transition or your gender could possibly “overshadow” my wedding. If your extended family’s bigotry ruins the wedding, that’s not your fault for being who you are, and I would never, ever think that or make you responsible for it, and I would want to help if I possibly could. Also, good news, there’s something specific and concrete he could do to help you:

After the invitations go out, he and your other brother and your brother’s intended spouse could call or email or text the people they are closest to and the people who are the most likely spreaders of family news in the extended family and say, informally:

Hello, you may not have heard this yet but [Deadname Sister] is now [Your Name/Brother]. I know it’s been a while since we’ve all been together, and I’m not quite sure how far he’s spread the word in the last year since he told us, but it’s really important to me that people don’t call him the wrong name or ask awkward questions at the wedding. This is a really happy thing for our family, and I’m trying to call up the relatives I can trust to be cool and supportive about this ahead of time so we can all relax and celebrate at the party, can you help me spread the word?

Principles:

A. Treating people like you trust them to be cool and supportive and telling them how they can show you that they’ll be cool and supportive is a good way to sort of back them into the corner of being cool and supportive.

B. As the groom, your brother use his clout as the person at the center of the event to everyone’s advantage: You in a snappy suit and your cool new name is not ruining the wedding, but someone making you uncomfortable would be ruining the wedding. “Behave yourself as a personal favor to me” may compel good behavior where, like, common human decency might not.

C. Getting the word out beforehand removes the drama of people being surprised in the moment. They’ll have a little time to react before you have to see that reaction.

D. Let your brothers absorb any “gross” “political” “religious” objections for you!

Script for asking him/them:

[Brother], I’m really happy for you getting married and excited to be at the wedding. I don’t want to put more work on your shoulders while you’re in the middle of planning this thing, but I also don’t want that event to be some kind of ‘big reveal’ of my transition – would you be willing to spread the word to our relatives and ease the way? I don’t interact with them all that much and I haven’t yet found the right way to get the word out.

Then, if he’s open to it, give him a rough script of what you’d like him to say and let him handle it. If both or either of your brothers are willing to do this for you, let them do this for you. 

You know your brothers best, and if they aren’t up for this or you don’t think it’s a good idea, then it’s probably up to you to call your most chatty and talkative relative or relatives and/or your coolest, most liberal cousins and spread the word to the people who can spread the word.

Hello [King/Queen Of All Family Secrets Far & Wide], how are you? I know we haven’t talked in a while, but I could really use your help with something. Don’t know if Mom/Dad told you, but last year I came out to them as transgender. I go by [Name] now, and use male gender pronouns and male presentation. I’m really excited for [Brother]’s wedding and for the chance to catch up with family I haven’t seen in a while, but I’m also a little nervous about it and I really don’t want this to be a big deal on someone else’s big day. Would you be comfortable spreading the word in the family for me, so it won’t be a surprise? I know you’re so great at staying connected with everyone, it would really help me out.”

Then you can give that person a little bit of Transness 101 as it applies to you, for example, “Please just call me [newname], I’d really rather not answer questions about medical stuff or “how did I first know” especially at a wedding, yes, coming out is hard because there’s so discrimination against trans people, but I’m happy to feel more like myself.

You may have to answer some of their awkward & gross questions and hear some religious platitudes, and I’m sorry about that. I’ve found “I’ve prayed about it a lot and I trust that God loves me” to be a good catch-all when the moralizing comes out, and bookmarking a good 101 resources so you can say “I don’t feel comfortable talking through all that just yet/I don’t quite know how to answer that question/This is all so new to me that I don’t feel like an expert yet, but if you want to read more about it I’m happy to send you some links.” The person’s initial reaction might not be their only/forever reaction, and if you can get them on your side and make a genuine connection, they will be a) honored to be “chosen” to be in on the “secret” and b) chuffed to be recognized for the work they do keeping everyone connected to what’s going on.

If you can, connect what you want them to do to helping your parents out, too “I’ve got great friends and coworkers around me, my brothers have been great, mom and dad are doing their best to adjust and be supportive, but I think that they are nervous about what the rest of the family will think, so you’d be helping them out a lot by spreading the word, too.

All this word-spreading is only a good idea if you think it would make you more comfortable. If you’d rather go completely low-profile the way you did at the engagement party, then fly low! If you were close to your family, they would know the important things about you, but you’re not and they are not, so, they don’t get to be mad that you didn’t call them up personally and audition your identity for them. One possible answer to “Wait, where’s [deadname]?” is “Not here!” or “Hey, I go by ____ now. Nice to see you, cousin!” or letting them wonder, forever.

I hate all this for you, my dear Letter Writer, I really do. You deserve love and a place in your family. You deserve to not have to take on all this emotional labor and risk so you can go to a party. My message to your family and all transphobic and homophobic people is basically:

twin-peaks-season-3-the-best-gifs-to-use-in-your-completely-normal-everyday-life-cr-1434873 (1)

Image description: David Lynch as Twin Peaks’s Gordon Cole, in a dark suit with an FBI badge and hearing aids in place, with the text “Fix your hearts or die.” He said this to the FBI colleagues of Denise when she transitioned from male to female. I want it on a t-shirt.

Now, let’s talk about the wedding itself.

Can you bring a plus one? If so, and if you don’t have a romantic partner who wants to go, I suggest bringing a good friend who is gregarious and able in social situations (that person who gets described as “Oh, ____ can have a conversation with anyone about anything!“) to be your buffer. If no “plus one” has been invited, I think it’s worth breaking wedding etiquette and asking your brother if you can bring somebody. If it’s out of the question, he’ll say ‘no.’ You’re not a jerk for asking in this situation.

If your brother doesn’t want to inform the family for you, who does he suggest you hang out with at the wedding? Can they seat you with the young & fun & liberal friend table? Was there anyone cool from the engagement party? “Brother, can you seat me with the cool kids, thanks” is a reasonable request. You’re attending to support him, but he’s the host of an event, and your safety & comfort are important.

Can you make sure to have your own transportation to and from? Sometimes just knowing that you can bail if things get upsetting can help you endure.

Can you be Chief Errand Runner and Behind The Scenes Helper? Can’t stop to talk about the state of your eternal soul or what you keep in your pants if you’re going to grab more ice!

If you can’t bring a buffer person, can you have a support system available by text? Sometimes being able to Tweet The Madness is the only thing that gets me through an awkward family moment.

Is there a safe, quiet spot (your car, the rest room, the coat room, outside) at or near the venue you can retreat to if you need a moment to yourself? Scout it out when you get there. If you need to bail at any point during the reception, bail. Your safety and peace of mind matter, too, and the groom is going to be way too busy with all the hoopla to worry if one guest left at 9:30 instead of midnight.

Gross politics are extra thick on the ground right now, and it sounds like you will be deep behind enemy lines. Decide if you’re more of a “Well, that’s a horrifying thing to say, Aunt Bea” person or a “Hrmmm these mashed potatoes are delicious and aren’t the flowers beautiful?” person, and lean into being that person. You don’t have to fight every fight right now when you’re just trying to survive. Adopt “I am here to support my brother, these people are not really important to me” as your inner mantra.

I was at a wedding deep in Tr*mp country earlier this spring and while everyone was on good, non-politics-talking behavior, seeing the super liberal Aunt-in-Law (who came out in her 40s)(and rolled up  wearing these magical Doc Martens) was a deep balm to the soul. Your family is not a monolith, and while I 100% believe you about why you stay away from them, I hope someone at that party is gonna be glad to see you exactly as you are.

I know a lot of our readers have been through similar situations, so, tell us what helped you.

This is also one of those times that I’m going to ask straight, cis- commenters to hang back and read more than you post. Transgender people get harassed, discriminated against, and sometimes murdered for their identity every day in this country and I’m not sure any of our “This is exactly like the time I had to deal with an awkward situation at a wedding” stories are the most relevant here.

We’re all sending you love.

 

Dear Captain,

I am desperately in need of some scripts. In November last year, my aunt launched an online women’s magazine. My aunt is a very rich lady, she doesn’t have a job, so she decided to focus on this project. It was a cool idea, based in some feminist principles, so when she asked me if I could translate the articles from our native language to English I was happy to accept the job.

The thing is, I considered it just that- a job. I’m a college senior, I have about a million things to do on any given day, and translating is time-consuming. She doesn’t really see it that way though- she thinks of it more as a “family favor”, doesn’t seem to acknowledge that I have other things to do and gives me ridiculous deadlines. Like, sending me an article at midnight and expecting it to be done the next morning. Or figuring I’d finish a 10 page text in two days or so. We’re close, she knows I have issues with asserting myself (I have BPD and boundaries are a real problem for me), and i have tried mentioning that I can’t really work like that, that she needs to organize things better so I have more time, etc. And she always agrees but then keeps doing it!! It has gotten so bad that I almost feel like she’s pushing my limits, or doing it on purpose because it’s easier for her to impose a ridiculous deadline on me than the people she has writing the articles (herself included).

To top it all of, she doesn’t really pay me… she paid me twice since November. And quite a small amount of money too (I had gotten 300 dollars total for eight months of work now, and what would, by word count, be charged at least ten times as much on a minimal rate). She also likes to try and pin other work on me- illustrations (because she thinks I’m creative!), photos, article writing…I’ve reluctantly done some of it, for no extra money.

She has this plan for me to translate A BOOK during the summer (she already decided that I’ll need about two weeks for that. Two weeks! For a book!) and I feel like I have to say something before I’m expected to slave over that instead of relaxing a bit after graduation. Though I would probably agree to it if I knew I’d get paid a fair amount and have a more realistic time-frame. She’s my aunt, and I don’t want to insult her or seem unappreciative, but I’m getting a bit desperate and I really need to sort this out somehow. Do you have some advice for me?

You don’t want to seem unappreciative? YOU don’t want to seem unappreciative? YOU think that YOU’RE the unreasonable or unappreciative one?

My sweet summer child, no.

It’s time for a meeting with your Auntie where you do the following things:

  • Present her with an accurate count of how many hours you’ve spent on this project.
  • Invoice her for those hours at a real-world translation rate. All of them. Every single hour and piece of “extra” work.

IF you want to keep working with  her on future projects, you 100% need to create a written agreement that includes, at minimum:

  • A defined scope of work and rates. Translation costs $x, photography & graphic design costs $Y, generating original content costs $z.
  • A budget of hours/week that you will spend on the project.
  • A defined invoicing and payment schedule
  • Guidelines about your working hours, frequency of communications, and turnaround times for work (with a HEFTY rush fee for rushed turnarounds). Set business hours, like, 10 am – 6pm, and after 6pm any emails or requests will be answered tomorrow. Her expectations about turnaround times are completely ridiculous.
  • A contract start date and end date, say, per project or for a period of 1 year. There is always the option to extend or contract for additional work, but by ending the first contract at one year it gives you a chance to renegotiate – raise your rates, re-budget your time.
  • Good starting resources: The Freelancers Union, The Freelancer’s Bible

Here’s a script for starting that conversation:

Auntie, I love working on your projects, but now that we’ve been at this a while, we need to more clearly define the project and my position here.”

If she balks at putting stuff in writing, “Auntie, putting things in writing protects everyone. That way the expectations are clear. I really can’t keep working without a contract.

If she suggests that you are ungrateful or suggest AT ALL that your rates are too high or that your totally 100% reasonable requests are in any way unreasonable, BAIL FOREVER. Literally, “Okay, Auntie, I understand if that won’t work for you, good luck finding a professional to help you, I’ll happily transfer all the files I have over to you and that person”(You will transfer them…as soon as she pays your entire invoice).

Other scripts, for the day-to-day times when she agrees to something and then tries to bulldoze you:

Sorry, that won’t work for me. I can have it for you by ____.” Then stick to that deadline. If she’s unhappy, she can hire someone else.

If that feels mean or like you’re the one introducing conflict to the situation, try to think of it as educating her. In my experience as a freelancer, a lot* of (rich) people like to start businesses without really knowing what is entailed. They want the title of “Editor in Chief” or CEO without spending the money to pay professionals or do the work to set up professional practices, and they are used to getting their way. It can create a toxic environment very quickly if it’s not checked. If she’s not purposely taking advantage of you (doubtful, but let’s do a thought experiment), she needs to know the actual costs of translation, graphic design, and editorial services so that she can make good decisions and keep her business viable. Your labor is valuable and essential to what she’s doing, so, she needs to pay you for that. Her money isn’t a gift or a treat or a generous indulgence she’s bestowing on you, it’s payment for your work.

She might try dangling the idea of money or a promotion to a full-time job down the road to get out of paying now. If she sees this as a joint project that you are creating together that she wants you to take over in the future, then, cool, she should treat (& pay) you like a creative partner. But that doesn’t mean she’s off the hook for the work you’re already doing. Your labor is a routine business cost. She better pay you, and if she won’t, find another job that will pay you, and let her figure her own shit out on the free market.

In Solidarity!!!

*#notall, of course, but one way to determine the difference is “Can I have an honest conversation about pay, hours, and other business matters with this person?”

 

 

Dear Captain Awkward,

This is a weird problem, but in my workplace, there’s an office phone that’s shared by everyone–though usually it comes down to me and one other coworker who spend the most time in this area. She’s started leaving these obscenely thick, full-facial-imprint layers of makeup on the phone. I don’t wear makeup, and I don’t appreciate getting it all over my sleeves or my face if I absentmindedly reach over to answer the phone–plus, you usually can’t see the layer of makeup until you’ve picked up the receiver and it’s too late. The backside of the phone looks fine–it’s the part that’s actually in contact with your face that’s a disaster zone. I’ve been just wiping the phone off every so often, but it’s only gotten worse, and frankly, I’m tired of cleaning up after her facial mess. It’s just gross.

I tried to be tactful and casually ask if she’d spilled something on the phone, but I’m pretty sure she had no idea what I was talking about and may have come to the conclusion that someone had gotten Cheeto dust on the receiver. At that point, I had to bail out of the conversation because I was having trouble keeping a straight face. I’ve talked to other coworkers, but no one seems to know how to deal with her. She’s got a history of overreacting to the smallest things, and we’re trying to do this without upsetting her. Help!

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Dear Captain,

Please share your wisdom. I have no idea what to do with a very good friend who might (or not ?) be in love with me and who never said anything.

Since our first year of college, 8 years ago, I have had this wonderful friend (let’s call him Iago). Lots of girls flirt with him but he’s never dated one (maybe once when he was 17 ?). Not sure if that’ relevant but another good friend thinks he’s secretly gay and maybe not even out to himself. He’s been there for me through hell, high water, and finals (and I was there for his parents’ divorce, etc.). Now we’re both in the same graduate program (that I sort of convinced him to get into but not so much because I don’t tell him what to do anymore). He was a witness at my wedding last year. He does not really get along with my husband but hey, I don’t get along with all my husband’s friends either.

Well, 2 or maybe 3 years ago he gave me a book for my birthday. I never read it because the first 10 pages bored me. A week ago I just found it, opened it, and it says on the cover (but I somehow missed it the 1st time) “For [me], an other [name of the hero’s love interest]”. I read the book and I don’t think it was meant in a funny way.

I feel so fucking betrayed. It was at least 2 years ago so I don’t even know if he still feels that way, but had he said anything, well, that did not happen but at least I wouldn’t have HAD HIM AS A FUCKING WITNESS AT MY WEDDING.

I can’t act at all, I can’t imagine what sort of conversation we could have, I haven’t seen him in 2 weeks and he’s beginning to find it unusual not to find me in the library.

I love him very much but I am angry, sad, confused. We used to support each other through our hellish program where we work 12 hours a day and right now, I’m thinking that he was never my friend.

Should I even try to have a conversation with him about this, 2 or 3 years later ? Should I just slowly African Violet him ?

I can’t unsee it. I don’t want to be selfish. I have been in one-sided love with a good friend once (and it was awful) but I just grit my teeth, stopped seeing him for a while, and waited for it to pass and it did eventually. I would have gone crazy if I had seen that guy as often as I see Iago.

I would be very grateful for any scripts.

Signed,

Wishing I’d Never Opened That Book (she/her pronouns)

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Hey Cap!

Okay so this is going to be a little complex, but  I hope that you could maybe provide some insight on the situation. 

I met a guy online (a long-distance situation) and we’ve been in contact almost daily for a year and a half now. We’ve gotten to know each other and it turns out that we’re on the same wavelength and get along so well. In the past I had asked him if he had a girlfriend because I didn’t want to get in the middle of anything (we have “intimate” moments), and he said no and that he used to but that he wasn’t happy. But just recently, he messaged me that he had finally broken up with his girlfriend! So my questions are actually:

1. Initially I felt hurt that he lied, but approaching the situation calmly,  it’s difficult not to comfort him, I mean we ARE friends and we do feel a little more than what friendship feels like. When he told me I politely thanked him for telling me and asked if he wanted to talk about it. 

When he opened up a little about it, he said that he thought that it would make him feel better, but after doing it, he felt sad. But he also kept telling me that it had been a long time coming, and that he had been wanting to do it for so long. I’ve never had happy breakups even when I was the one to break it, so I told him that sadness for a while is normal, and that if he had wanted to do it for so long then, there’s a fundamental basis for it that’s obviously important. So now, how do I actually comfort him?

2. I’m confused about the situation. At times he tells me that I make him smile, that he wants to be with me, and I believe because if I didn’t, then we would’ve stopped talking ages ago. The connection and attraction that we have are both pretty strong, and I actually want him and want it to work, and I have plans to see him in a few months. I don’t know what to make of it – him telling me that he’s now free, how he initially feels about it, and so on. So Cap’n, can you please help me make sense of it? Thank you Cap’n!

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Hello Captain,

My distant friend Sally and I went out to dinner and she started asking me about my past relationships. I’ve known Sally for over a decade and she’s never pried into my dating life. I told Sally I wasn’t interested in dating anyways as I am looking for a job and like to online date or meet people through work. She tried to reason me out of all of this which seemed troubling.

A couple weeks ago Sally had a birthday party. She had put the event on Facebook. After our dinner, Sally texted me that her friend John saw me on the invite list and became “interested” in me. She said he might hit on me at the party ( he did not show up). This made me uncomfortable as I hate flirting with strangers. It’s odd but I’ve never even flirted with someone who’s become my boyfriend.

I also don’t trust Sally’s judgment at all. To be blunt I’ve met her friends and they aren’t horrible but they’re the “I don’t suffer fools gladly” type.

John has also been asking Sally about me. He wants to know when I’ve found a job and want to meet him. I have never indicated I want to meet John. I’m refusing, there’s something odd about a person in their late twenties being this invested in someone because of their FB profile. I rarely if ever post on FB. He is also asking me out through my friend which seems manipulative.

Do you have script suggestions?

Thanks,

– No thanks stranger ( female pronouns)

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