The "Ask vs Guess" name rhetorically frames it in favor of the Askers. Asking sounds reasonable, guessing does not! But really it's not about "Guessing", it's about understanding. It's about community, and relationship, and trust. What this culture really wants is for you to pay attention and understand the people around you, rather than treating everything as a transaction.
You shouldn't feel bad for asking for help when you need it and other people haven't noticed it, and it's good to be mindful of those around you and what they need. A balance of both should be healthy.