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be an asker
Helen Frankenthaler, Riverhead, 1961
My mom was the one who taught me how to be insistent. When I was a kid and she was trying to change a flight reservation or persuade someone to do something she would spend literal hours on the phone—she’d just keep calling back until she found someone who would do it. At the time I found that super embarrassing, as kids do. But looking back, I see that I internalized something important: how to ask for what you want.
To be clear, I don’t mean this in the sense of you should harass people. Asking in the wrong way can be bad, and asking when someone’s given you a firm no can be very very bad, so there’s some level of emotional sensitivity required here. But those are the exceptions, since most of the time you are not going to be penalized for asking. You penalize yourself: that’s why you don’t ask. But if you’re able to stop punishing yourself for asserting your needs, something very important changes. You become capable of advocating for yourself. 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).
This mostly applies to platonic/work situations (romantic/sexual situations are way more fraught and I may dedicate a separate post to them). Other notes:
It is generally way more effective to ask a lot of different people than to ask one person many times (they’ve probably made up their mind, unless the situation changes a lot).
The best cure for rejection sensitivity of any kind is to get rejected a lot.
When you get a lot of nos and then eventually get a yes, it helps you learn 1) how to get a yes and 2) many narratives you have about yourself are probably mistaken.
If you are marginalized/less privileged, you will probably receive a lot of more nos. That is wildly unfair and there is no easy solution.
I think a lot of people who don’t ask for what they want explicitly end up resenting themselves and resenting the world. I’m speaking from personal experience because I used to be very against asking, and I definitely think it set me back. I have three friends who are incredible askers, and watching them live their lives was what inspired me to change. All three of them share the exact same qualities:
They don’t have much of a filter and freely voice their needs
However, they’re not coming at it from a needy place—they’re genuinely super chill and are fine with hearing a no; they’re also good at making people feel like it’s safe to say no to them
They’re very warm people (you want to say yes because you like them) and fairly attuned to other people’s needs (they’re giving as well as willing to ask)
As a result, I think all three of them have had a lot of success in their work lives, friendships, and romantic relationships. Aspirational, right?
I think the trickiest thing here (it’s been a multi-year journey for me, personally, so I get that it’s difficult) is sort of why PUA stuff exists and all these relationship manuals sell a bazillion copies—it’s really hard to fake security when you’re not secure, and asking just works a lot better if you’re coming from a secure place. However, I think that practicing asking can help you become more secure. So if you want to be more of an asker (this post is inspired by this Maybe Baby essay about ask culture vs guess culture, by the way), I would identify low-cost ways to ask and starting practicing those.
One example: I literally used to be unable to tell hairdressers how I wanted to get my hair done. Like, they would suggest giving me bangs (bad, bad, bad, bad) and I would know I didn’t want that but somehow just go along with it. Why???? Eventually I realized I was being silly and now I come in with very specific instructions. But I think this kind of scenario is perfect for practicing because obviously this trained professional wants to give you a haircut you don’t hate.
Slightly more difficult: reaching out acquaintances you want to meet up with (for ex, via Twitter). Lots of people are really nice and will oblige you. But also lots of people will ignore you, and that’s okay too!
Truly difficult: being honest about your needs in important relationships (friendships, partners, etc). I think like 85% of people just absolutely can’t do this, so if you can, kudos to you.
Anyway, living a fulfilling life aside, asking is good because it saves you time. It’s amazing to me how many people find roundabout ways to lightly hint at what they want when they probably could’ve saved themselves hours and hours by just asking directly. You may think your hints are super obvious, but most people are not paying as much attention to you as you think they are. If you really, really want to know what the answer is, just ask.
Asking also makes you better at answering questions. People who are indirect often end up being dishonest just because they’re so uncomfortable with the prospect of saying no. Examples: buying something you don’t want, ghosting someone after a third date, lying when you are definitely not planning to hang out with someone again. Obviously, it’s good to be tactful, but I think most people would benefit from being significantly more direct.
Directness is a gateway drug to emotional honesty. That’s my take, anyway. I’m curious what you think: are you an asker or a guesser? Do you want to be more direct, or do you think subtle hints are underrated? Do you feel like you usually get the answers you want to hear?