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Hello Captain!

I think my friend (30F) resents my work-life balance? For a while now she’s been making these weird comments that I don’t know what to do with. I’m a freelancer (also 30F) with a lot of flexibility as to when I decide to get my work done and business is doing well! I’m happy. She works in corporate and is always complaining about being overworked. I wouldn’t mind that – I’m happy to emphathize but it’s often in passive aggressive ways?

I really try to not provoke her but it feels like I can’t say anything. The last time we called (it was a group call) I mentioned rearranging furniture in my room and she said: ‘Ha, you must be so bored’. Me: ‘No I wouldn’t say I was bored.’ Her: ‘Ive been wanting to clear out the fridge for a year but I have just so much work.’ Me: Silence

Also on that same phone call I said I was gonna make a coffee before meeting with my next client. It was a state holiday. My friend asked if I work today and I said yes. Then she goes: ‘Well at least you can take a break. I could never take a break during my normal work day’. Me: Aha. Moving on.

So it’s not like I’m shoving vacation pictures in her face. But she resents me mentioning I was shopping for groceries in the morning and stupid shit like that. I’ve stopped arranging meetups with people during normal work hours in the group chat she is because it really seemed to trigger her ‘well someone has to work!’ but I can’t keep from saying shit like ‘I’ve done a non work related thing’ or ‘I’m working’. She went to the same uni I did and could easily do the freelance job I do now – I’d be happy to help her out and offered previously. I don’t know what to say when she react like this and it’s getting on my nerves.

Lately I’ve been saying nothing and just letting the silence sit. Should I confront her about it? How? Or am I being to sensitive about it? It makes me want to not talk to her at all. I’m not sure she’s realising what she’s doing.

Hello! If I’m reading this right, it feels like your friend is negging you with these little comments, but you’re not sure if she’s doing it on purpose or if it’s worth calling her on it. You’ve been handling things just fine, sounds like, but now you have ample evidence that responding with silence does nothing to interrupt this dynamic and it’s still annoying you, so it’s time to try something else. Here are a few more active strategies you could try. All of them are designed to give you a way to test whether she’s doing it intentionally and interrupt the cycle, while also giving your friend the maximum good-faith opportunity to course-correct. Sound good?

Strategy One: Pattern recognition + Information diet

Your friend calls you, asks you what you’re up to, you tell her, and then it kicks off, right? Maybe…almost…. like she’s asking the question to give her an excuse to be weird and critical about it? Stop telling her what you’re up to, or use much less detail.

Her: “Hey, glad I caught you! And what are you up to this fine day?”

You: “Nice to hear your voice! What’s going on with you?”

Answer her question with a question. Or, even better, lie and say you are working, and see if that changes it.

Her: “Hey, is this a good time to talk?”

You: Sure! I just finishing up some work, but I’ve got a few minutes. Why, what’s up with you?”

I do not like lying as a rule, and I do not like people who make me feel like I have to lie, so I”m not suggesting this as a long-term approach. Think of it as an experiment, where for the next 10 calls from this friend where she asks you this question, working on work is work, so is housework, so is working out, so is working through your latest binge watch, so is working on catching up with sleep if she happened to catch you napping. Working on figuring out what’s for dinner? Technically work. Working on your golf swing? Through great effort great achievements are possible.

A person with no ulterior motives is going to roll with whatever you say you’re doing, and you’ll have a chill, normal conversation. A person who was hoping for a little fix of building herself up at your expense is going to get frustrated by this, and look for something else to latch onto. This is exactly what happened on that holiday when you had a meeting, right? “Well, at least you get some breaks.” Why not have a little fun with it and see how far she’ll go? If she gets bored and stops doing the annoying thing, you win.

Strategy Two: Meet passive-aggression with aggressive positivity.

Her sub-textual bullying can’t land if you ignore the subtext and engage only with the text of what she said. Is it true that you get more downtime in your workday than she does? Sounds like it. Do you feel insecure about how your schedule compares to hers? It sounds like you don’t, at all, so what happens if you treat her implied insults as if they are something between neutral, accurate observations and sincere compliments?

Her:“Must be nice to have so much free time.”

You: “You’re right, I love having such a flexible schedule!”

Her: “Wow, I could never just take a coffee break in the middle of the workday like that.”

You: “I agree, it is pretty great to be able to pace myself and set my own hours.” 

Her: “Well, *someone* has to work while you’re off [rearranging the furniture][making yourself the occasional beverage][running errands].”

You: “Hahaha, you’re so right! The best part is, if I bang out my work early enough in the day, I get to hit the grocery store in the afternoon when it’s not crowded and I don’t have to go on the weekends when it’s a madhouse in there.” “As you know, freelancing can be pretty all-or-nothing, so after a couple of busy weeks to hit deadlines, it’s really a relief to have some down time to catch up on the routine stuff.”

Be inexorable about turning every dig into sincere appreciation.

Why this works: If she doesn’t intend to be mean (doubtful, but let’s go with it for a second), then you’re just “yes-and”-ing her in a pleasant conversation. If she does intend to put you down, she’s gonna have to work much harder at it, meaning, she’ll either get bored and back off or your Ted Lasso-level positivity will annoy her so much she’ll change tactics to something more aggressive-aggressive where it’s crystal clear that she’s being mean to you on purpose and then you can deal with her on those terms.

Strategy Three: “Are you okay?”

This works best in person where you can see each other’s faces, and like the compliment strategy above, it works best when you wait for there to be an immediate example of the bad behavior rather than trying to discuss the overall dynamic in the abstract. Once she does the thing, pause, look her in the eyes, and maybe put a concerned, gentle hand on hers  and say, “Are you okay?”

Her: “What do you mean?”

You: “I asked if you’re okay.”

Her: “Yes, I heard you, but why?” (or “Of course I’m okay, why would you say that?”)

You: “I dunno, one second you were complaining about how hard you have it at work, which is valid, but then it felt like you were trying to put me down for having a different schedule. Was that your intention when you said [repeat back what she said, including her tone]? Something just feels ‘off’ so I’m asking, are you all right?”

Why this works:  If she’s doing this unconsciously, like it’s just a rote reaction to compare herself to other people to make herself feel better, then you’re calling it out in a direct and gentle way that gives her a chance to catch herself, apologize, and clarify her intentions. And, while I try to be a shoulder angel most of the time, allow me to put the shoulder-mounted devil costume back on for a minute: If she’s being mean on purpose, gently asking if she’s okay is actually a reverse-Uno condescension masterpiece that will drive her up the wall, but you’re not doing anything overtly mean to escalate the situation.

Remember, people have choices about how they treat you. She could say, “I’m so sorry, I didn’t mean to insult you, I’m just stressed out at work and frankly a little jealous of your ability to have more control over your time.” At which point you could say, “I understand if you need to vent about work sometimes, but can you do it without making little digs about my supposedly cushy life? Whether or not you mean it as a put-down, it feels like one and I’d like you to stop comparing our schedules from now on.”

Or, she could turn this into a bad-faith referendum about how she was “just joking” and the real problem is how you are just “too sensitive,” etc. For that, go back to the strategy of agreeing with negs until you can get the hell out of there. “You’re right, my schedule is better and I do have more free time. That is a problem….how?” “You’re right, I am sensitive when a friend can’t seem to talk about her own problems without making digs at me and my life.” “You’re right, I didn’t get the joke or find it funny! I guess we should probably stop talking about topics where we have such a different view of things.”

Strategy Four: “You’re being really weird about this.” “This is boring, let’s talk about something else!” Also known, broadly speaking, as returning awkwardness to sender.

There’s a very specific kind of bullying attempt that happens when an insecure, toxic person who is heavily invested in a cultural narrative that Following Certain Rules Will Make You Both Happy And Better Than Other People encounters an inexplicably (to them) happy person who stubbornly refuses to follow (or give a shit about) the same rules. I think you might be in a situation where this fits. .

Story Time [with content notes for fatphobic bullying and body stuff]: Long ago in the late nineteen hundreds I worked at a place where there were a ton of white women in our 20s who did roughly the same job. We became friendly, often ate lunch together, and went to happy hour and did fun stuff outside of work together occasionally on weekends. One of them I’ll call “Shelly” was obsessed with two things:

1. Being thin.
2. Getting a boyfriend.

For Shelly, these things were inextricably linked. Boyfriends were achievements that could be unlocked by becoming sufficiently thin, and both of these goals gave her an excuse to practice constant vigilance and constant comparisons to other women. You might wonder what she did when presented with incontrovertible proof that some fat women had boyfriends.They were obviously sluts! She sounds fun, right?

Shelly was not even close to my first ride on the Mean Girl Express, but I’m not a naturally confrontational person and I was actually mostly fine with tuning her crap out in group settings for the sake of hanging out with the coworkers I liked. Unfortunately, Shelly decided that I was meant to be her Sidekick/Fat Best Friend/Punching Bag and started singling me out, and the way she did it was *very* specific:

[A comment on whatever I was eating/wearing] + [A backhanded compliment about how she wished she could be that confident/careless] + [A reminder of how virtuous she was being by comparison] = Me wondering “What the hell just happened?”

“Oh my god, your sandwich looks so yummy! I wish I could have avocado on mine, but they have soooooooo much fat.”

“What a cute outfit! I didn’t know that [Retailer] had pants in bigger sizes now, back when I got mine I had to diet so hard to fit into them. I love your confidence!”

She loved to shop on her lunch breaks, and her favorite way to shop was to go to stores where nothing would fit me besides earrings and have me be an audience while she tried stuff on and she lamented about how fat everything made her look. It only took one of those for me to decide that being alone with her or going to a second location was not for me, so then she started bring bags of her “fat” clothes to the office to see if I wanted any of them before she donated them to charity, knowing full well that they would not fit me. Sometimes my shoulder angel wins, and I say stuff like “Oh, no thank you, but I appreciate the thought!” and sometimes shoulder devil is like “Oh, thanks for thinking of me, but our… tastes… are very different” while I rub the feel of the plastic garbage bag full of pilled acrylic sweaters the color of old mustard off my hands as if I’ve touched something gross and sticky. Don’t remember which shoulder bud was ascendant when, but eventually she did stop trying to foist her cast-offs on me or cajole to “Come on, just try them on!”

The thing with this kind of bully is that they *are* conforming to entrenched cultural narratives, so there is a lot of ambient background support for the idea that they are just striving in a normal way and anyone who doesn’t do the same is the problem. Mine was going all in on fatphobia, and yours is going with rise-and-grind capitalism, but the bargain they think they are making is the same. “I follow the Rules and do things Right, ergo I Deserve to be Happy and Successful!”

If other people manage to be happy and successful on their own terms, without putting themselves through the same hoops, these people find it between mystifying and threatening, depending on how miserable they are at any given moment. What good are the rules they’ve chosen to dedicate themselves to if the people who don’t follow them aren’t punished? You don’t have to openly antagonize them, you just have to exist where they can see you and that’s enough to constitute a personal attack on their way of life. In other words, if it’s possible for you to have a fulfilling career AND free time, then you exist as evidence that maybe the long hours your friend is putting herself through at work are not entirely necessary, and that’s scary for her, so she’s reminding herself of what she’s been taught about how all of this is supposed to work. If she were truly happy and secure with her choices, then she wouldn’t need to sell herself (and you, by proxy) so hard on the notion that her way is the best and only way. 

Like you said, if your friend feels overworked and is genuinely interested in how you pull it off, she could ask you for ideas about transitioning to something with a better schedule. If she were just venting about her situation, you could be a sympathetic ear. But the way she keeps making digs at your life shows that this isn’t about leaning on you for support.

I felt bad for Shelly, because her unhappiness was visible from space, but I flat out did not like her enough to hash any of this shit out. I was never going to convince her in a million years that the things she valued (male attention and having the smallest possible physical mass) were not worth the misery she was inflicting on herself and others. Would she have benefited from being professionally screened for eating disorders, or some other kind of therapy? Probably? Even if I had known such a thing existed, would she have listened to such a recommendation from The Fat Girl Who Embodied All Her Greatest Fears? Nope! I was not a Captain of Awkwardness yet but I did know that I was not causing her to behave like this and that trying to fix mean people is wasted effort. Any attempts to engage her on that level would have ended with her doubling down. But I did successfully get her to start avoiding me and stop talking about diets, etc. all the time by reacting authentically to how incredibly odd her behaviors were and how they made me feel without ever engaging with the substance of the comparisons.

“Wait, did you just mentally count the calories in my sandwich?” :nervous giggle: “Should we….like…go around in a circle so you can compare your lunch with everyone’s, or are we good with just mine?”

“Do you keep a spreadsheet of my clothing sizes somewhere? Can I see it?” :awkward pause: “Or do you do all the math in your head, that’s amazing!” :longer, more awkward pause:

“Oh, we just talked about diets and men yesterday, can today be for finding out about what books everyone’s reading lately? Or, we could talk about boys and books. This dude I went out with the other night brought me a copy of Confederacy of Dunces and said it was his favorite book ever and now I have questions.”

I’m riffing off of remembered vibes here, not recreating actual conversations word for word, and I definitely mixed it up with the turning negs-into-sincere-compliments thing without realizing it was a strategy. She’d give me one of her backhanded compliments, and inside my head, I would be like, wait, she said I was “so confident” but I think she meant it as an insult, but actually, I *am* pretty confident, so, yay for me! “Thanks, Shelly! You look nice, too! What’s everyone reading lately?” She HATED it, which is how I know she was being a bully on purpose. She mistook the fact that I don’t default to Mean Girl mode as a sign that I was incapable of matching her energy, and well, everybody learned some new things that year.

Why this worked: We were surrounded by fellow nice white ladies who were also on perpetual 1990s fat-free diets who did not really “do” open conflict, so they were no help whatsoever, but as long as I kept my tone pretty light there was nothing for them to latch onto except the subject-change-shaped-conversational-life-preservers. Over time, a few people who genuinely liked Shelly and wanted to talk about the same stuff closed ranks, and all the non-miserable folks were set free be lunch buddies with only some diet talk, some of the time.

To implement this with your friend, wait until a conversation where the pattern forms, and then keep your tone very, very relaxed and flat. “Huh, so strange that you keep comparing our schedules even though we do different jobs, what’s that about” (not really a question) and then change the subject. “Are you venting about your work schedule or criticizing mine? I lost track for a minute.” “I love it when you ask me what I’m up to and I think it’s going to be a fun conversation and then you immediately imply that I should be doing work.” “Did my ancestors send you to check up on my degenerate lifestyle again.” You’re not being mean or escalating conflict by calling attention to the conflict.

Strategy Five:  This person is your friend, and ultimately, directness is kindness. “It’s really strange that every time we talk about our schedules, you compare yours to mine in a way that feels insulting. What’s that about?” (actual question) “You keep doing this thing, do you realize? Well, now you know, so are you going to keep doing it?” “I really value our friendship, so I want to address this with you and figure out another way.”

Her answers will tell you everything you need to know about whether this is a friendship worth preserving. Life is too short for frenemies who manufacture excuses to be mean to you.

P.S. If you’ve seen the word “weird” in the news a lot want to talk about Returning Awkwardness To Sender as a political strategy, there’s a post over at Patreon all about that.

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