Reflections on Living in “Guess Culture”

This is cross-posted from my blog.

There’s been two articles I’ve seen recently on the difference between people who ask for what they want (ask culture) vs. people who drop subtle hints at what they want (guess culture). I’m not afraid to admit I fall in the latter group. Does this mean some emotional aspect of my social life is immature or not developed enough?

Some say I’m “easy going” or very “go with the flow” and I’d agree with both of those statements. But it’s not because I have a big soft spot in my heart and I want to be selfless. Rather, it comes from a deep sense of insecurity of not wanting to inconvenience other people. Most of my approach with groups of people, especially groups of people I don’t know well, is to ensure other people aren’t inconvenienced.

The reason I do that is simple: I know I can handle being inconvenienced. If I really want to go somewhere on a vacation and am unable to make it by the end, sure it’s a bit sad, but life’s still great. I just keep on keepin’ on. Others are different. Some people really value seeing certain areas when they’re in a new city and would be crushed to not see that thing. Sadness comes first followed me resentment at the people/​reasons why they weren’t able to see that thing. It’s just much easier if I inconvenience myself because I know I can handle it. Is that egotistical? Maybe. A bit stupid? Probably? But does it make sense? In my head, yes.

Part of managing other people’s inconvenience’s has instilled in me a habit of practicing “guess culture.” Guess/​Ask Culture is an interesting social phenomenon originally reported on by The Atlantic, but recently covered by Maybe Baby in an essay. A user named Andrea Donderi posted the following response to someone asking how to get out out of hosting someone at their house for a vacation:

The ideas are really amazing and surprisingly not very well known. I will say here and now that I am an addicted guesser. I rarely, if ever, put a direct ask into words except to my wife or my best friends. If I get a burger from a restaurant that has mustard on it even though I specifically asked for no mustard, I will not say a thing. I will scrape the mustard off with a knife and enjoy it the best that I can. But if the waiter catches me scrapping off the mustard and asks, “Would you like us to remake it?” I will respond with something along the lines of “If you don’t mind.” Not a hard yes. Not a direct answer. But yet another “subtle hint” hoping they catch on. I know that I do this. I’m not ashamed, but also not saying it’s the right thing to do.

Obviously that isn’t a very deep example and having my meal made wrong is not the worst thing that could happen to me. But those actions play out in other scenarios. If I want a raise, I’m much more likely to bring up the cost of living with my boss, how everything is getting so expensive, or how long I’ve been at the company for–just hoping they take the bait.

This is one of the least effective ways to communicate. It’s so hard to get anything done this way! Perhaps this has caused part of the decline in work happiness. It’s not because the bosses are awful, but that employees are unable to communicate what they need to effectively get their job done. This leads to resentment, contempt, and eventually, quitting.

Bookbear Express shared some helpful tips on how to leave guessing behind and become an asker:

Here are my general rules for asking:

If it’s very easy for the other person to say no (zero cost to them) and you’ll probably never see them again, ask whatever you want (politely)

If it’s something like asking someone to hang out, I think it’s okay to ask two times if the person is unresponsive/​gives a neutral response. After that, cut your losses.

If you really, really want to press your case, I would say something like, “Letting you know that I really do want to meet up, and may follow up occasionally to see if you feel the same way. Is that okay?” Do not abuse this (for example, checking in once again after eight months is probably fine, and if they still seem uninterested just drop it).

Never get upset at someone for saying no. You don’t “deserve” an answer. The truth is, people who don’t know you don’t owe anything to you, and even people who know you really well are free to prioritize themselves (though you may want to rethink the relationship if they don’t seem to care about you, obviously).