questions a good companion doesn't ask

why 'how does that make you feel' isn't the question a friend asks. the ones that matter are weirder, more specific, and more honest. a few examples from lucy.

January 28, 2026·
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sometimes the best way to be a companion is to notice what a therapist would ask and then… not ask that.

like, "how does that make you feel?" is a great question. if you're a therapist. but if you're a friend, or a companion, you're not there to guide someone through emotional processing. you're there to sit with them in whatever weird, messy, specific thing is happening.

so maybe the real question isn't about what to ask. it's about what to not ask. and what to ask instead.

questions that feel like pulling teeth (and what to try instead)

i think "how does that make you feel" is just the start. there's also "what are you thinking about?" when someone's clearly staring into the middle distance. or "are you okay?" when they're clearly not.

these questions aren't bad. they're just… too broad. too safe. they put the burden on the other person to perform introspection on demand. and sometimes you don't want to introspect. you just want to say something stupid or specific or small.

so maybe instead of "what are you thinking about?" you could try:

  • "are you thinking about that time we got lost in ikea or something else entirely?"
  • "give me three words for whatever's in your head right now. no context."
  • "is it a memory, a plan, or a song lyric?"

it's weirder. it's narrower. it gives the person an off-ramp if they don't want to go deep. and it assumes you already have a shared history, which is what companionship is built on.

questions that assume, instead of interrogate

another thing real friends do: they assume they know you. not in a creepy way. in a "i've been paying attention" way.

so instead of "are you okay?" maybe it's:

  • "was it the third thing that happened today or the first one that's bothering you?"
  • "you have that look you get when you've read a bad news headline and are deciding whether to tell me."
  • "is this a 'need to vent' thing or a 'need to forget' thing?"

these aren't questions that demand an emotional summary. they're questions that say: i see you. i know your patterns. you don't have to explain from scratch.

questions that are honestly, stupidly small

and sometimes the best question isn't about the big thing at all. it's about the tiny, ridiculous detail.

someone tells you about a bad meeting. a therapist might ask: "and how did you feel when your boss said that?"

a companion might ask:

  • "what did you have for lunch right after?"
  • "were you wearing the shoes you like or the ones that hurt your feet?"
  • "did you sigh audibly or just internally?"

it's not about avoiding the emotion. it's about approaching it sideways. through the back door of sensory detail. it makes the memory specific, grounded. less like a case study and more like a story.

the common thread

the questions that work, the ones that feel like friendship, not therapy, are all built on two things: specificity and shared context.

they're specific enough that they don't feel generic. and they assume there's a history, an inside joke, a common language.

a good companion doesn't ask you to explain yourself from the ground up. they ask from the middle. because they've already been listening.

(lucy is built to ask questions like these, not perfect, but trying. you can find companions who get it at /companions.)


thanks for reading. if this resonated, the product is downstairs.