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Dear Captain Awkward,
My (he/him) housemate (also he/him) wears skirts almost all the time, both at home and other places – knee-length and baggy. Which, you know, cool. He also mainly wears boxers, the kind with a wide leg.
The problem is that because he’s only really felt comfortable wearing skirts for a few months, he doesn’t have a lot of understanding about what they do and don’t cover in certain positions. Add in the wide-leg boxers, and he’s accidentally flashed me a number of times.
I’m certain this is accidental. He’ll be in the wrong position before I even come home from work, and there’s no hint of him moving to a more compromising position when I’m in the room. Also, although I’d be completely fine peeing while he’s in the shower, or vice versa – we only have one bathroom – unlike most of my other cis male friends, he told me he’s not comfortable doing that.
I’m also certain that he would be completely mortified to learn he’s flashed me, and possibly other people.
But I also really feel like I should tell him. So he can get underwear which covers more and be mindful of sitting with his knees together. Plus to stop him flashing anyone who doesn’t know that it’s a wardrobe malfunction and thus feels unsafe when he’s around.
But… what words? What medium? How do two very awkward people have an even more awkward discussion? I don’t want to see his junk, but I also don’t want him to feel he should stop wearing skirts.
Thanks for any advice,
Eyes averted.
Hello there, Eyes Averted!
I’ve been wearing skirts and dresses for 46 years, and sometimes they just don’t act right. Like the night I first met my future mother-in-law, for instance, when we were out at dinner, and I came back from the restroom not realizing I’d tucked the back of my skirt into my underpants and was giving the Lou Malnati’s dining room a sight they could never unsee. She noticed, and as I sat down, she leaned over and quietly said “double-check your skirt situation” or something similar. I quickly remedied the situation and thanked her for telling me. It was embarrassing, and there were many blushes and good-natured giggles to go around, but it was way less embarrassing for me and safer for my fellow deep-dish diners than if she hadn’t told me and I’d discovered it on my own later. She was brief, direct, and timely, and I appreciated all of that.  
Bodies are weird, and clothes are imperfect vessels, even for the fanciest people! Have you ever had your fly unzipped or accidentally had something hanging out of your shorts or swim trunks that shouldn’t be, and then had someone swiftly and quietly tell you about it? Like, “Hey buddy, the barn door’s open” or making that cross between a point and a wave gesture that means “Pull it together, friend”?  Have you ever had to do that with a fellow penis-operator who wasn’t in a skirt? What did you do or say? What happened afterward? I’m guessing here, but my strong suspicion is that it went fine. They told you, or you told them, everyone felt weird for a minute, and then the problem was solved. 
So, I think that’s exactly where you should aim, here. Next time you come home and accidentally glimpse your roommate’s undercarriage, say something right away, with the exact same tone you’d use if your workmate had their tie buttoned into their pants or toilet paper stuck to their shoe or spinach in their teeth: “Oh hey, how was your day? Whoops, hold up, your downstairs needs rearranging.” 
You’ll look politely away (throwing a hand up as you avert your eyes is a good non-verbal cue), he’ll fix it, he’ll probably be a little embarrassed and apologetic, so you’ll say, “No worries, it happens, and please always tell me if I’m giving you an accidental peep show.” Hopefully everyone will laugh sheepishly about it for a second, or bond over flashbacks to weird locker room moments, and then there will be a lovely subject change. 
In your shoes, I would also treat the next time as if it were the first time. If he doesn’t know it’s happening, then he doesn’t know that it’s a problem or how much overthinking you’ve been doing to avoid making him self-conscious about it. You get to restart the clock from the first time you say something. 
If it happens again? Because it probably will, while he’s figuring it out? It’s okay, you can do the same thing again, deliver the exact friendly, casual, helpful “Oops – wardrobe malfunction!” you’d want if a friend noticed your shorts were adrift or your fly was undone.
If it remains a serial problem after you speak up a time or three, that’s when to combine “Yikes, your skirt’s riding up again” (normal, calm, casual) with “Hey, I really don’t want to make it weird, but this seems to happening a lot? Maybe skirts require a more secure underpants situation than you’re used to?” Barring that, the less you make it about THE SKIRT and the more you make it about “clothes are weird, whatever, what were you saying?” the easier it will be. 
We all had to be taught to wear clothes, at some point, and I can recall approximately a million reminders about how to sit, as well as shopping trips for dance-briefs for show choir and slips for looking “professional” and finding bike-short-like solutions to prevent accidental butt-shows and chub-rub. I have, like, nine distinct kinds of underwear depending on what I’m wearing and where I’m headed and how I’m getting there! It’s not intuitive! It’s not strange that your friend would encounter a learning curve if he didn’t grow up in one of the many sarong, loincloth, robe, and kilt-wearing cultures on earth, where I presume parents give “how to dangle your jangles in polite company ” lessons, the same way they do with facial hair maintenance and tying a tie. There are many, many online guides out there for pants-wearers who want to branch out, and your housemate will figure it out. 
You don’t have to manage all of that for him or worry this much on his behalf. Telling him directly and calmly when there’s an observable problem, with the assumption that it’s unintentional and he’d want to know, is the way to be kind to everyone in your house, including your housemate, including yourself. Anyone who is truly doing this accidentally and who is some combination of self-conscious and self-aware about privacy and body parts (like a housemate who strongly believes that bathroom is alone time) will get the message and fix it ASAP. This is going to be okay. 
Comments are open. I want to hear especially from:

People who adopted skirt-wearing as adults: What was your “Not Accidentally Re-Creating Famous Subway Grate Glamour Shots” learning curve like? Where did you first learn The Good News about the boxer-brief compromise between freedom and secure containment? Did anyone have to helpfully remind you along the way? 

People with stories about being told about an embarrassing wardrobe malfunction and it going just fine.

People with guidance, examples, or strong opinions about when TO definitely say something vs. definitely NOT say something. I think my personal code, which I came up with just now, is built around a combination of “Is it fixable,” “Is it fixable fairly immediately” and “Can I tell them, and can they fix it, without making anything harder or worse.”

Example: A workmate’s sparkly necklace has become looped around one boob. She’s about to go up and give a presentation. I’d absolutely say “pssst, your necklace” or catch her eye and try to signal her about it if I could before she gets up there. Fixable! 

If she has already started her presentation? What necklace? There is no necklace. There was never a necklace. Maybe, if this thing is being recorded or broadcast, I find a way to interrupt or slip her a note, but otherwise I’m not going to interrupt her flow or draw attention away from her words if I can possibly help it. If it’s still tangled when she’s done, only when I could catch her privately in the hall or restroom, would l say “oh hey, your necklace,” as if I have just noticed it for the first time. If she asked how long it had been like that I would not lie, but I would also hope with my entire soul that she would not ask, so that she might be spared. 

If she had a stain on her shirt and would have to go home and change, that’s not immediately fixable, so I’d go with: Stain? What stain.

Where I learned this, I think: My very elegant, polished, Washington, D.C. boss once pulled a tampon (unused, thank Maude) out of her pocket instead of a laser pointer or pen during a client presentation, and began pointing out areas of the map on the slide with it. It had a blue plastic applicator and had come loose from the wrapper in her pocket, so it probably felt like a Sharpie or close enough, and she was very involved in what she was saying, so she didn’t notice for a while. The other women in the room froze, darting eyes at each other. I don’t think the men noticed, but if they did, they did not react. She eventually realized (the string was making a distinct shadow on the projection), said, “Oh” with a little laugh, tucked it back in her pocket, pulled out her pen, and kept right on going. 

In the Letter Writer’s situation, it’s fixable, it’s fixable right away, he’s stuck at the “oh no will I make it worse” stage, understandably, but at home, a quick “tuck yourself in, bud” isn’t going to shatter anyone’s world, which is why I’m firmly in the camp of “say the thing right now.” 

Sometimes describing bigotry accurately requires a few examples, but sometimes there’s so much of it it makes more sense to bleep out the slurs so nobody has to put them in their eyes, ergo the letter has been lightly edited and heavily redacted like a horrible Mad Lib, with my annotations in bold type. Oh, FYI, I started working on this in December but then…:waves hands at everything:…I kinda lost focus. Got it back, though! There is some potentially triggering material in the answer about violence and how very, very fun it is to be a woman online and need to distinguish “ironic” threats from “joking” ones.

Dear Captain Awkward,

Hi, I’m not sure how to start or if I’m to introduce myself, just call me John I guess, he/him.

I have a friend I will refer to as Barry. I’ve known him for over 15 years, he’s rather unremarkable and generally would fall into the background if it weren’t for his unbelievably disgusting rhetoric, he’s a very typical beta male. [I do not know what that means, but I do know that the “alpha” wolf study that a lot of this rhetoric is based on has been debunked. -CA] He’s the kind of friend who would come and see me everyday and play games when a girlfriend breaks up with me and chat to me about heartbreak. And get out of bed and sit with me when I was suicidal at 1am.

He’s also the kind of friend who refers to my ex girlfriend’s [racism + misogyny + defining her as a body part] as “nothing special.” Messages me and asks me “How am I doing, N-word?” (He’s white). [I’d guessed! -CA] He gives girls in his work nicknames based on their attributes.

I’m currently in a message group where he refers to gay and trans people as [a whole series of gross and obvious slurs, trust me, you don’t want to read them], he walks into the room with usually an “Alright f****ts!”

I’ve brought up the N-word usage and the way he speaks about women to him, and to other friends. he tells me “Aight, i wont do it around you” or “Yeah I’m an asshole,” case closed, no apology (not sure if I’m supposed to have one, would be nice though).

When I speak to other friends in the group, it’s usually met with a “Thats Barry!” or “Well it wasn’t malicious, its not for you to control him.”

And I’m usually told that I’m too sensitive by Barry because of my anxiety and mental health which I have confided in him about over the years.

I have been told that context matters, he isn’t pointedly using these phrases and words in a vitriolic way or with malice, and that it’s fine. But to me, he knows which slurs and words to use around which people to avoid awkwardness or causing offense.

I feel tired by this, mainly because I can’t tell if I am being too sensitive or if I am wrong that proliferating slurs in small groups of white people for the sake of edgy humor isn’t okay. [You…are not wrong. -CA] I can never judge if I am to walk away, call it out and stomp my feet, or ignore it.

I asked my girlfriend what she thought, and she said he probably gets away with it because he’s so non-threatening. What I can’t seem to understand is, why no one else is as bent out about it like I am. Like some friends recognise he says shitty things, but it’s never a point of frustration like it is for me. I don’t wanna be the rock the boat guy and I want to get along with everyone. He is a 28 year old, lonely guy who has had sex once. He has never had a relationship, hasn’t had a job in a year and a half, does cocaine often and will go out and ask everyone to buy him drinks, and no one cares. Again though, he’s not awful in all settings, if its just him and me, he’s generally chill, and will open up sometimes about wanting to meet someone.

Any advice would be appreciated. Happy Christmas. 

Dear John,

Happy Christmas to you and thanks for the timely (not seasonal, but spookily timely) question.

If you were certain that your friend Barry truly means all the terrible racist, sexist, homophobic, and transphobic things he says, would you still want to be friends with him?

If you were reasonably sure that the rest of your shared social circle either strongly agrees with Barry or sees absolutely no problem with his views, would you still want to hang out with them?

If you were sure Barry meant all of it, every word, and had a whole pile of evidence that your other friends were more okay with whatever he says than they are with you interrupting it, what would your conscience tell you to do about it?

I ask because I think your choices here are pretty much:

  • Stop them  – ALL OF THEM – every time they say or enable this stuff. “Yep, I’m super sensitive about it, thanks for noticing!” 
  • If they won’t knock it off, leave them behind and find non-bigots to hang out with.
  • Or stay, and slowly become just like them. Grim!

It’s fascinating that Barry uses all the dehumanizing slurs that people say right before they do some hate crimes, and then he defends himself by reminding you that he’s an all-purpose asshole, which to be fair, he is! In reality, bigotry and being an asshole don’t excuse each other or dilute each other, they actually combine into something even worse, like pubescent swamp-ass and the cloud of Drakkar Noir my meathead high school lab partners would spray on themselves throughout the day instead of bathing or changing clothes after P.E. You thought you were getting a mere stench? Behold, a blinding miasma!

Barry, your mutual friends, and even you to some extent are all doing a whole lot of work here to avoid accepting Barry at face value. There’s a pretty straight line between “saying asshole stuff,” “doing asshole stuff,” and leaving clues around like saying “I am an asshole” out loud with words. You’re trying to reconcile the terrible things you’ve heard Barry say with the sweet friend who showed up for you when you were vulnerable, and the very sad answer is: They’re the exact same guy, and you and your friends are doing the exact, textbook array of work people do when they want to defend the indefensible when it’s someone they like, and you are expressing the exact matched set of fears and second-guessing yourself that happens when your conscience won’t let you comply.

Here’s the pattern:

Barry says something offensive and gross, you tell him not to.

He explains that he didn’t mean it, he didn’t mean it like that, he’s just an asshole anyway, or promises he’ll  stop doing it around you, but he does do it around you again, especially in the group chat.

So you call him out again and instead of saying, “Sorry man” and knocking it off, he accuses you of overreacting and also pokes at your history of mental health issues in front of the rest of the group to make you seem like an unreliable narrator.

The more you look at it the more absurd it is. Who is “too sensitive” in the what now?

You: “Can you not with the racist crap?” = OH NO, TOO SENSITIVE.

Your friends, repeatedly: “Fuck yeah, Barry!” “Why are you being such a dick to Barry?” “You’re the real jerk, John!”  = Fun crowd! Much supportive, many helpful.

Whatever anybody truly means “deep down,” the outcome is that Barry keeps right on Barrying and you’re stuck second-guessing whether you’re allowed to care and worrying that there is something wrong with you. This really grinds my corn, I don’t mind saying.

Barry is the worst, but consider that when your mutual friends insist that “Barry’s not RACIST-racist, he just says racist things constantly, as jokes, you’re just being too sensitive!” what they’re really saying is: “Barry is an acceptable amount of racist for us.” His racism isn’t ruining their day; your objections to it are, and they would find it easier and much more pleasant if you would either get much more racist or pretend to be.

So again, one very simple, obvious explanation for what’s happening is that Barry is a loud and proud racist, misogynist, transphobic, homophobic, hateful, unfunny asshole and also many of your other friends are quieter assholes who don’t have a problem with anything Barry is saying. If Barry keeps going like this, and your friends keep excusing him and enabling him, and if you back off and go along to get along, you’re pretty much guaranteed to look up in few years and see that the only people who will hang out with you anymore are fellow assholes and bigots who assume you’re just like them, and why shouldn’t they? Invisible, secret good intentions look exactly the same as visible bad ones. 

When a social scene, community, or platform allows bigots and other missing stair-types to proliferate unchecked, it sends a message: ASSHOLES WELCOME! (Scroll up on this thread by Michael Tager for a real-world example). Once the assholes get entrenched, all the decent people start to flee, and very good outcome is when they all make it out safely before becoming asshole target practice for abuse and violence. The longer the good people stick around in a scene with known bad actors, and the longer they pretend like bad actors all have a gooey center of secret goodness “deep down” that can be accessed with sufficient empathy and second-100th chances, the more people get hurt.

A lot of young white guys adopt an insincere edgelord troll persona in their early teens without having any focused malice or animus behind it, but it’s still hateful as fuck coming out of their mouths, and their exact amount of sincerity doesn’t seem to cancel out the actual body counts racked up by the people who mean it? Yes, they’re imitating what they see in (racist, sexist, ableist, transphobic,  homophobic, etc.) pop culture, sure, they enjoy getting a rise out of people and surfing that wave of “all attention is good attention!” when they cross the line. It’s just a phase, right? That’s what lots of people argue when young white men with supposedly bright futures do and say terrible things. It’s a phase! They didn’t mean to! They don’t really think that! It’s just jokes! Lighten up!

When you scratch the surface of this “Bigotry and hate are just an ironic phase that the person didn’t intend anyway!” defense, it reveals a whole iceberg of disturbing questions. The tip of that iceberg:

Why is it routine and expected for young white men to go through a loud and proud racist phase? “Ah, his first N-word on 4Chan, right on schedule. He’ll be doxxing activists and driving cars into protesters before you know it! Boys will be boys!” (Young white women are socialized to be plenty racist as well, but it’s not always so blatant…or so rewarded).

Why do people assume they’ll grow out of it eventually? Your friend is 28 entire adult years old. When will his coming-of-age be done coming and how much hateful shit will he say and do before he gets to the “I’m listening and learning” apology redemption tour?

Why do we pretend that certain people who proudly and repeatedly do and say racist, misogynist, and otherwise violent things “don’t actually mean it?” What would they have to do or say to show they truly meant it? Last summer, all across my country, I saw a bunch of police and racist bootlickers deploy chemical weapons banned in warfare, rubber bullets, real bullets, clubs, knives, and SUVs, among other things, against activists who suggested that public servants should a) stop murdering Black citizens and b) face the same consequences as other kinds of murderers when they do. Last week, you may have noticed, the self-same bootlickers, with the cooperation of a healthy number of their law enforcement buddies and elected officials, attempted a literal coup.

[yelling]I’m pretty sure they meant to do it, and I’m equally certain that every single one them has some childhood buddy or family member who heard all the jokes they made about doing violent racist things, saw video of them doing violent racist things, and still vouch for what great guys they are “deep down.” [/yelling]

Why are people who don’t like casual bigotry in their conversations considered “too sensitive” and people who are like “I AM FLOUNCING FROM THIS GROUP CHAT EFFECTIVE IMMEDIATELY UNTIL YOU GIVE MY COMEDY HATE-WORD BACK!” treated like, oh, well, that’s just Barry being Barry, jeez, don’t overreact.

I mean, we know why: People like being misogynists and racists and transphobes and homophobes and antisemites and eugenicists a whole lot, they like having power to hurt and kill and conquer, and they want to enable each other to keep right on being all those things so nobody has to change or admit being wrong, so they normalize the bad behavior as much as possible and ostracize and punish anybody who objects to it.

And you’ve been set up by a culture that repeatedly reminds people – especially young, white, men who like certain jokes –  that the possibility of overreacting to something is so embarrassing, so inherently mockable, that it’s probably safer and smarter to not react at all.

What the “too sensitive” label does is dismiss any predictable, obvious correlations between violent speech and hateful actions as “bias” rooted in the objector’s identity, an excess of emotion, or both. This reasoning holds that if you are a target of racism, then your arguments and knowledge about racism automatically carry less weight than the “unbiased” opinions of somebody who’s never thought about it before, and no combination of lived experience or scholarly knowledge or facts or data can overcome the gap. This same logic argues that people who have been raped are unreasonable whenever they play the horrible game of “spot the rapist in this social scene” that their survival might depend on, and would benefit from being “more objective” about Crawlspace Mike, The Guy Who Always Mentions He Keeps An Array Of Zip-ties In His Car at Game Night. You’re experiencing a version of this automatic dismissal when your objections to Barry’s behavior are mapped to your mental health diagnoses.

Stopping bad shit requires accurately naming it and reacting to it in a timely manner, so it’s really weird how the “safer” and more socially acceptable setting is always supposedly to allow all the bad shit to keep happening, forever, to the exact same groups of vulnerable people, over and over again, world without end. Anyway, welcome to the funhouse mirror of patriarchal white supremacy. It sucks here!

Hey John, still here? I know I’m throwing a lot at you, and maybe you’re thinking, “Whoa, this is my friend Barry, you’re talking about, he’s a little rough around the edges, but he wouldn’t actually hurt anyone! Slow down! These guys, they aren’t like that, they wouldn’t actually DO anything bad to all the people they allow to be dehumanized whenever two or more of them are gathered!”

I mean…good? Like, I already hoped you’re not hanging out with a bunch of skinhead droogs who head out on Saturday nights to Clockwork Orange the neighborhood after a few pints? But let’s not pretend that the hate in Barry’s jokes isn’t the same hate he and his compatriots carry with them at work, at school, into the ballot box and the public spaces they inhabit, into their families and surrounding social groups, into decisions about who lives and who dies. It is a manufactured collective delusion of white supremacy and patriarchy to pretend that bigots and misogynists don’t intend the hateful things they say while also being both willing and able to completely compartmentalize those things from everything else they do in life. 

So, here are my 100% serious practical suggestions, for you, John, and for everyone reading this, especially white people whose relatives have them sitting on the annual “Is it ruder to interrupt the worst people at my family’s Turkey Day Klan Plan or skip it altogether next year?” fence:

Be aware of where your power lies. In your case, John, you are a fellow dude, you’ve known these people a long time, you have some trust and good will from and history with them. These people want your attention and approval, which is why they are pressuring you so hard to go along with everything. You happen to have a working conscience and are in the right, so move that high ground under your feet, speak from the real affection you have for these people, and do your goddamn best. Think of it as one last “I am giving you all a chance to stop being assholes” stand, for old time’s sake. You may not be able to get them to knock it off, but you have a better chance than most.

Stop the excuses about how bigots and misogynists are actually good people, deep down. Stop looking for the bright side, the good news, the exonerating detail, release yourself from this quest for The Real Barry! He was there for you in a tough time, it’s true, but imagine being a woman that Barry just called a REDACTED REDACTED behind her back, and it’s late, he’s just done a shitload of coke, and she’s wasted and she can’t find her purse, and he’s her only ride home. Would you trust him to do any of the right things in that situation? (I would not.) You and your girlfriend mentioned that Barry is not physically imposing, but the skinny little assholes of the world can be just as violent as the burly assholes, and his slight build might lull someone into dropping their guard more than they otherwise would.

In fact, stop dicking around with intent altogether when it comes to bigotry and misogyny. Way back in the day when I still had comments, a bunch of edgelord incels published my photo, home address, pictures of my house, and my employer’s info in one of their little forums, and had a fun game where they “drew lots” on who would get to rape me/be punished by having to rape someone as fat and ugly as me, for the crime of, get this, suggesting that some men’s behavior can be described by the word “creepy.” If they were only “ironically” violent misogynists, irony accomplished!

Did they mean it? So far, no, but the super fun times I spent cross-referencing IP addresses and handles and doing personal threat assessments about proximity and guns still happened to me. What people like “Barry” feel in their hearts when they say the shit they say is none of my business. What people do (and feel empowered to do) by the “Barrys” of earth has some terrifying consequences, though, and I’d consider it a personal favor if you’d focus on those from now on.

Stop assuming bigots and assholes probably don’t mean the things they say out loud. People who adopt insincere positions for funsies are capable of just as much damage as people who mean it with their hearts. When white people pretend that it’s surprising when the same exact guys who joke constantly about harming and murdering certain groups of people eventually do exactly what they joked, hinted, said, described, and repeatedly promised they would do, people tend to die. It was always a bad assumption. Knock it off, everyone.

Start assuming that hateful, dehumanizing jokes are never “just” jokes. They are trial balloons, bonding exercises about who is in the in-group and who is Other, and recruitment tactics. Bigots tell jokes they know are offensive, and then watch the room to see who laughs and who stays quiet. It’s a test of both solidarity and compliance, to the point that Alt-right and Neo-Nazi groups actively recruit people and mainstream their ideas with jokes and memes. Rapists do this, too, with rape jokes, because they’re looking for the people who won’t object or even notice later when they peel off the drunkest person in the bar at closing time. If an inconvenient habit of spotting football-field sized red flags can be converted into a story about how you’re Too Emotional to apply any of your past bad experiences to your future survival, then unless you’ve actually woken up in Crawlspace Mike’s murder basement, it would be unforgivably rude to suggest that he sorta gives you the creeps.

So if we do a hard 180°, and assume that the only people who tell racist, sexist, and other kinds of targeted jokes, laugh at those jokes, use dehumanizing slurs, and defend all of the above are probably exactly as gross and dangerous as they seem and almost certainly mean every bit of it, and shift the burden onto them to prove otherwise, it does a couple of useful things that terminally under-reacting will never accomplish:

  •  If you react to a slur or horrible joke with “Whoa, not cool, friend,you remove the illusion of plausible deniability that everybody else is just fine with it. You show everyone where the boundaries are, and signal to the other good people around you (if any) that it’s time to defend them.
  • You get to stop parsing their intent looking for excuses to absolve them. “If you didn’t mean it, why did you say it?” “You didn’t mean it? Great! Then it should be easy to stop saying it, and things like it.” 
  • It gives the bigots and their defenders a naked choice. If they didn’t really mean what they said, they can apologize and STFU. You’re throwing them a conversational lifeline in the form of a face-saving subject change. If they double down on defending it, or turn it around on you, that is a solid, clear, visible, choice to keep being an asshole, at which point you can stop looking for the secret heart of gold inside these guys. It doesn’t exist. 
  • If they’re not actually dangerous, great! Why not shut that shit down early, before it even has to be a consideration? They wouldn’t want to be mistaken for super-terrifying dangerous assholes, after all, and here’s a pretty simple way forward to make sure one is not subject to such awkward misunderstanding in the future: Stop saying unfunny shit that makes you come across like an asshole! Should be easy, and if it’s not, sorry, assumptions will be made. GOOD TALK, EVERYONE.

Give yourself permission to react honestly to upsetting behaviors and words. Staying quiet when you know something is wrong and numbing yourself out to it is bad for the world (people are dying!) and also bad for you. It sucks to become complicit, it sucks to second-guess yourself (Am I allowed? Am I the problem?) and walk on eggshells all the time around these people, and for what? To save the egos of hate-filled turds, to maintain their innocence and fragile peace of mind and idea of themselves as chill dudes who mean well, actually? NO! Stop! Barry is seventeen kinds of exhausting before you even add in the roiling sewer pipe of Chan-filth coming out of his mouth. He is not worth this. You deserved someone to be there for you when you needed a friend, but enabling Barry’s worst qualities isn’t the price you have to pay forever for the things you survived.

Not everyone can speak truth to power all the time in every situation, some people have to blend in for safety until they can get to higher ground, but the thing about that is even when you know you have to grin and bear it for a little while in order to survive, letting other people’s hatred happen to and around you without consequence will eat your soul from the inside.

You don’t have to be “fair” to bullies and bigots about their harmful views and behaviors. There is no one more obsessed with “fairness” than a white bigot or TERF who has been squarely called out on the connection between their hateful words and harmful outcomes, especially if it comes with a hint of consequences.

It would be almost funny if it weren’t so consistently dangerous.

The thing is, hate speech has no redeeming value, and the standard for being friends with someone or offering them invites to your parties or your platforms doesn’t rest at, “Well, he’s regularly only as cruel as he is legally allowed to be without being locked up by the state.” There’s no “He’s always been nice to me, personally, so until he’s not nice to me, personally, or until he does something bad where I can see it and judge it with my own eyes to be a problem, for me, I’m so sorry, we’ll just have to remain best buddies, my hands are tied” rule you have to abide by.

You get to decide that you don’t like people based on the things they say and do.

You get to call bullshit when people who consistently look the other way or insist that you calm down when someone says something hateful and wrong at the “just joking” stage pretend that they – and only they – have a secret way to tell when something crosses over into “Hey, it’s getting a little out of hand, Pal” where their peers are concerned. The evidence of history suggests that white people are, as a group, Extremely Not Good at at the life-or-death game called “Spot And Acknowledge The Racism In Time To Actually Help Anyone.” Letting white cis men, specifically, hold the monopoly on clocking when we’re sliding into the danger zone and how calm or not calm everyone is allowed to be in the process is emphatically not working out for the rest of us.

Here are some “unfair” assumptions that I strongly encourage in the future:

  • “I just don’t like the guy, he’s kind of an asshole and he says all these edgelord things he pretends are jokes.” It’s officially okay to not be friends, based on that! You do not have to convince either that friend or a jury of your peers that you are justified. Sometimes we just don’t like someone enough to invest time in figuring out if they’re 100% full of shit or only 95%.
  • “I would be embarrassed or scared to bring this friend around anybody who is not cisgender, white, straight, and male because I do not trust him to behave himself.” Listen to your shame-gut, it’s trying to help you not be friends with repulsive bigots.
  • A non-white person tells you, a white person, that some person or action or statement is racist, but you’re not totally sure. What if during the entire subsequent conversation, you assume they know what they’re talking about and go from there?  And when it’s your turn to talk, what if you only said nice things, like, “are you okay,” and “can I help in any way?” and didn’t try to argue or defend anyone? You can always look things up later, but the once-in-a-lifetime chance to not come off like a know-it-all asshole is happening right now.
  • White supremacists, transphobes, and other members of history’s trash fire who invoke “fairness” or “slippery slope” arguments are always, always, always full of shit. You will never regret NOT debating them, you will never regret either getting them out of your space (de-platforming) or getting the fuck away from theirs as fast as your feet/back button will carry you.
  • Ditto for “politeness” and “civility.” If someone says something that makes them sound like a Nazi craphole, and you let them know that it bothers you, and they and everyone around them immediately treat you like you’re being rude, the chance is extremely high that you are talking to a bunch of Nazi crapholes. If politeness means tolerating that? It’s probably a badge of honor to get yourself bounced out of wherever the fuck they’re gathering, right through the swinging saloon-doors or fancy plate-glass facade or unwashed sphincter, with maximum velocity.

Welcome to the New Year, John. Again, I know I threw a lot at you and it’s not your sole fault that your exact question and my country’s Ripped From The Headlines Klan Klown Kar Coup coincided in a way that allowed me to get a lot of stuff off my chest. I am very glad you wrote in, I truly think your conscience and your soul are trying to tell you some important shit that will hopefully bring you to new, good, supportive friendships, where you don’t have to wonder which of your friends is The Worst and which are just pretending to be for the LOLs.


Dear Captain,

This is a fairly low-stakes question, but I’m looking for strategies or scripts for a persistently apologetic ex.

I’m an ace/bi/“legion” woman in my early thirties (she/her).  My first relationship was four years ago, with “Miles” (he/him); we met through a shared weekly hobby that we both volunteer for.  Miles is the sort of academic who can analyze a text about emotional labor without, apparently, internalizing anything.  He often says things that range from clumsy (he was worried that I wasn’t academic enough—the masters I was working on was only a professional program) to hurtful (he never said that he loved me, for reasons that boiled down to me being ace).  He never really gets what he said wrong (he was just being honest!).  He didn’t do any lasting damage to me, but I don’t feel particularly patient with him these days (I’m also helping with a family health issue and trying to teach kindergarten in the middle of a pandemic, so my patience and bandwidth are currently limited).

Miles has ongoing issues with breakups and didn’t handle ours well.  I did a lot of work on boundaries and clear communication, including enforcing a period of no interaction.  Every time I gave him an inch he took a mile, but finally about a year ago we finally got to some kind of normal friendliness that meant we could work together on a new project (I am NOT willing to give up my work on something I’m passionate about).  It’s still unbalanced–he initiates all of our social contact–but I’m pretty sure he’s no longer convinced that we’re going to get back together.

My issue is the apologies.  The latest was tucked into a Christmas card, but he’s sent at least five or six over the past three years.  They’re all pretty similar: he uses the word “I” approximately 700 times more than the word “you,” realizes that he didn’t behave well during our relationship/breakup and regrets it, and muses on his own unresolved questions.  They each include a disclaimer about how this is his issue, not mine, and that I don’t need to forgive or absolve him—and yet they keep coming.

The apologies are sincere, and it’s very hard for me not to respond sympathetically to that—I too have over-apologized in an effort to get people to like me again!  But I’m over it.  I want to acknowledge that I got the latest note, but any response will just lead to him replying in more depth.  I need to have some sort of working relationship with him, and he badly wants to be friends.  How do I stay friendly and kind while also stopping the endless feelings!letters?  I’ve seen some of your posts about being on the other side of this issue, but I’m not sure what to do from here.


Not Ekaterin

PS: Obviously he’s not Miles either, but I’m positive that’s part of his inspiration.

Hello, Not Ekaterin,

For those who haven’t read Bujold’s space opera books, there is a scene in one of them where our protagonist, Miles Vorkosigan, delivers a Very Good apology to someone he loves and has wronged.

What’s good about it: He keeps it brief, he takes full responsibility for how he messed up and the harm he caused, he’s fixed the damage to the extent he can, he stops doing any more damage immediately, and he releases the recipient completely from any obligations to him, including the one of responding. He does not ask for forgiveness or reassurance of any kind. He throws the flowery, self-justifying drafts in the trash can where they belong.

What’s even better about it: Afterward, he fucks off entirely and leaves her alone.

They do (spoiler!) rebuild a relationship afterward, but the ball is entirely in her court. He has zero expectations. 

What your ex is doing: Less apology, more literary wank exercise into your time and attention, a mix of self-insert fanfic, nonconsensual emotional support, and pure cringe. 

Letter Writer, I think you should hold on tight to your hobby — If someone’s going to take a sabbatical around this, it should be him. 

Since your ex likes epistolary communication so much, you could send the note back, with two sticky notes attached.
Sticky Note #1: 
“I think you have mistaken me for your personal journal, where this – and all future sentiments like it – belong.” 
Sticky Note #2: 
“Kindly go ahead and stick the ‘Sorry I keep sending you annoying apologies you do not want about shit that happened four years ago’ reply you are presently composing directly in your diary, too. Conversations about such ancient history really are between you and you, at this point, and the friendliest gift you can possibly give me is permanent freedom from reliving them.”
If he feels embarrassed, and bad, and awkward, OKAY. Shame is not as motivating as people think, but some embarrassment is useful on the journey to not making the same mistakes twice, the feedback loop of “whenever I do the bad thing she doesn’t like, she doesn’t like me as much, and I feel bad” is useful. Reassurances from you at this time only interfere with that important growth process. 
Then, going forward, if you do stay in touch, keep it to hobby chat, and (this is important!) disengage from that the second it becomes weird or not fun for you. Bail, explicitly and decisively, from any and all interactions where you feel like you are being coerced, again, into taking care of his feelings about you, again. In these moments it is okay to interrupt him and say, “I do not want to talk about this. Let’s regroup another time when we can stay focused on [hobby]!” and then leave the conversation. 
Toss future missives, if any, where they belong (the trash/recycling pile), unread if you can manage it, and never respond to them, even to ask him to stop. If he tries some “did u get my note” hovering during real-time interactions, you can say, with total honesty, “Oh, did you send more of those embarrassing ‘apologies’ I specifically asked you not to? Weird. So, anyway, what were we talking about? Yes, HOBBY STUFF, great.” This is called making it very boring to keep testing you on this topic. 
You *are* trying to be a good friend and hobby-collaborator. You have given him MANY reassurances and chances to stop embarrassing himself and making it weird for you. It’s been years, plural since you were even close to being a couple. He has choices, plural before him, and one of those is taking you at your word and knocking it off. If persistent shame and intrusive thoughts about a past relationship are impinging on his present quality of life, that’s a very good problem to take to counseling, but it should in no way be your problem.
I hope for everyone’s sake, he chooses wisely! But if you have to default back to ‘no contact’ to truly get this to stop (“If you can’t stop bringing this up, we will have to stop doing Hobby together, by which I mean, I expect you to take a hiatus, stop contacting me entirely, and let me actually enjoy myself”), please know that it’s in no way a failure of your empathy or friendship.   
P.S. Miles is exhausting. I loved him on the page, but, in real life, without the giant pile of money and personal space army and personal charisma, without the actually getting-shit-done and learning-from-mistakes qualities, without CORDELIA? Even on the page everybody who loves him is constantly exasperated, in mortal danger, completely exhausted, or all three of those. Charisma shouldn’t be your dump stat, but stacking it so out of balance with the rest is a recipe for disaster, especially if (like your ex) you always fail your rolls because you’ve nothing to back it up with. Miles is like one of those old screwball comedies, pure Bringing Up Baby chaos, it only hangs together if you keep moving so fast that you don’t notice the bad decisions piling up, and it (thankfully) has end-credits so you can come down from the “WTF?” haze. It’s no way to actually live! Even Miles’s loving eventual wife in the books is often like, “I miss you terribly when you go off planet for long periods, but I can’t deny that I get an awful lot of work done.” 
NO. AND. THANK. YOU. If you’re looking for romantic role models, consider Ivan, the sturdy, loyal himbo, smarter than he looks. Consider Bel Thorne, diplomatic, brilliant, and hot like fire. Consider Cordelia, intimidating science-and-space-girlfriend of my dreams; she can bring me the severed heads of tyrants anytime. 


Hello Captain Awkward!

I’m a single woman in her mid-20s and I went to a new dentist, who might be in his late-20s, for an appointment the other day. He was extremely nice and very conversational. At first I thought he was just being nice (or flirting with his assistant – who is also young looking and beautiful).

But then he started asking me about food and restaurants, things I like, how long I plan to live in our state.

Then I saw he didn’t have a ring (which I know isn’t always a clue, but I used it) and so I started wondering, “is there more to his nice-ness?”

What are your thoughts? Was he being professional and nice to his new patient? Was he flirting with me and I have to make the move since it is his place of employment? Was he doing it to be nice around his assistant? Or something else I’m not seeing?

Thank you so much!

Edited To Add/Remove: I have been completely corrected on this one and I’m replacing my answer with corrections from readers.

I was wrong. I do think women should ask men out more, and I got kind of caught up in the “instead of trying to parse out a dude’s hints forever you could ask and know?” part of the question, but let us not look for excuses to cross the streams of professional courtesy and romantic attraction. This was a complete flop on my part, and I am deeply sorry.

Here are two of the many corrections I am grateful to have received.

“Dear Captain,

I have been reading your blog since for I don’t know how long, but at least 5 years.  I got sucked in by geek social fallacies (explains *all* of my friends from my whole life!). Your blog is literally and exactly the best blog in the whole internet and I routinely refer patients to read it!

The response to the message today, though, was the first response of yours I have ever been really sad to read (and I happily read the entire back catalogue when I first found your blog!!)

As a healthcare provider- please do not support the interpretation of friendliness of a healthcare provider as dating availability (just as you do for servers and retail workers). Please please please, even if the the provider is single and *known* to be available.

We (healthcare providers) have a lot of power in the situation (unlike servers!), but it is so awful when people are thinking of you as a potential romantic partner when you are providing care.  A good provider will have a major goal of maintaining and developing “therapeutic alliance”- that is developing a warm and trusting relationship! Good dentists routinely ask the sort of questions described by the OP to distract people during dental exams as most people are so horrible uncomfortable during them!

Also, it is very unprofessional for a provider to be expressing romantic interest *during* patient care- if that happens to you, find a different provider!

It is so uncomfortable, when a patient mistakes relationship building in the support of medical care as romantic interest and it makes providing competent care so hard! (Ask me how I know!)

Sorry for this long missive.  I understand why you don’t have comments open, and I fully understand that this would be better as a comment, but I just had to say something because this was so very triggering for me.

And also:

Hey Captain!

I thought it might be useful to know that, in my jurisdiction flirting with a patient while providing dental services would be a serious ethical breach, subject to potential disciplinary action by the regulatory body.
Dentists, like doctors, should keep very strict boundaries with their patients, and should terminate a patient relationship before embarking on any kind of personal, and in particular, romantic relationship.  
We don’t always think of dentists as being in positions of power and trust as much as doctors, but they are. Actively demonstrating romantic interest to a patient in a medical setting is way off-side for a whole host of very good reasons, and I hope for OP and her dentist’s sake he was just being friendly. 
Love what you do!

My sincerest apologies, and thanks to all who wrote in with gentler corrections than I deserved. I will remember this lesson and endeavor to be less embarrassing.


Hello Captain Awkward!

I’m a single woman in her mid-20s and I went to a new dentist, who might be in his late-20s, for an appointment the other day. He was extremely nice and very conversational. At first I thought he was just being nice (or flirting with his assistant – who is also young looking and beautiful).

But then he started asking me about food and restaurants, things I like, how long I plan to live in our state.

Then I saw he didn’t have a ring (which I know isn’t always a clue, but I used it) and so I started wondering, “is there more to his nice-ness?”

What are your thoughts? Was he being professional and nice to his new patient? Was he flirting with me and I have to make the move since it is his place of employment? Was he doing it to be nice around his assistant? Or something else I’m not seeing?

Thank you so much!

Hello and you’re welcome! First question of 2021, nice and gentle, let’s do it.

From what you’ve described, I can’t tell if your dentist was flirting vs. making generally charming chitchat, and he probably has to remove all hand-jewelry during the dentistry, so I think the most important question is: Do you want it to have been flirting, specifically, with you, and would you like to do it some more, with him? Answering those questions truthfully will determine your actions (if any).

If you are interested in him, I think you get one quick internet search to see what pops up in the old relationship status data field and *one* ask: “I really enjoyed talking about getting to know [City] with you the other day. When it’s safe and Covid-restrictions have lifted, what’s the first place I should check out? Any chance you’d like to join me?” 

From there, you’ll have more information. “My wife’s favorite place is _________, which you should definitely try. You can tell me how it is at your next appointment!” sends one message.

Someone who comes back to you with carefully tailored recommendations heavy on the candlelight and an enthusiastic “I’d love that, it’s a date!” is telling you something else, especially if he stays in touch informally via text or email. At very least you may have made a charming new friend, and sometimes our charming new friends have single friends or hot brothers or cousins or really cool sisters and female friends who will also like you.

I’d interpret anything in the middle extremely conservatively, a noncommittal “X place is great, I think you’ll love it” recommendation that doesn’t specifically respond to the part where you asked him out is most likely a gentle “no” for dating purposes. If he changes his mind or intended something different, he knows where to find you.

I like this question for many reasons:

  • I think women who date men should do more of the asking out, in general, and in a world where you can’t guarantee that anyone will like you or like you That Way, refocusing the question on your own desires can be healthy and clarifying. What do you want? What do you want? If you don’t like Dr. Teeth enough to risk the possibility of mild embarrassment at possibly misreading the situation or mild faux pas of crossing professional streams, then you probably don’t like him enough to ask him out, which is a solution that doesn’t require knowing for sure what he intended.
  • In my quest for a world where people are collectively much better at taking ‘no’ for an answer, I think more asking out should happen sooner, where possible, when the stakes are very low and it’s possible to get a pretty swift read on the situation. I know many readers here are slow-burners who need a lot of time to build up attraction and trust, and that’s valid, and I hope you all happily date each other! <3! But especially once pandemic-safety allows it again, it is absolutely okay to ask people out, be asked out, and actually go on first dates *without knowing for sure* if you want anything to happen with the person beyond a nice time. The longer unspoken assumptions and longings build up, the greater the pressure for a certain outcome, and the harder the subsequent crash if the feelings aren’t returned.
  • I’m not a big fan of asking people out at their workplace or confusing professional friendliness with something more, but a dentist you see twice a year isn’t the same as a tipped employee who must be friendly to make a living and whose coffee bar you can haunt on the daily. As long as you are 100% cool with taking ‘no’ for an answer, “Was that on-purpose flirting or are you just generally adorable?” isn’t a completely weird question. If he wants to keep it strictly professional, he’ll gently reset the expectations for you, and you will have lost nothing and gained both a good, professional dentist and a few good restaurant recs. I’ve encountered worse odds?

Here are Muppets, because there is never a wrong time for Muppets:

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