I wonder if guessers don’t have good boundaries, and so they’re afraid to impose on others. If you can’t say no to people, you might avoid putting other people in a position to say no so you dance around the subject.

Then, when someone with good boundaries comes along and outright asks you for something, they seem rude because they’re putting you in a position to assert a boundary and you struggle with that.

One thing this old article doesn’t get into… Is why some people are guessers. Because they were raised by guessers? Because they grew up in the Midwest?

When I first learned of this, it was presented in a way that made sense to me, which is that through interaction with our family during childhood, is when you establish whether you’re an asker or a guesser. Families that are confident, loving, and communicative, are askers. They can communicate in this way because they know they are loved, so they can more easily articulate boundaries, precisely because they know they’ll be respected.

Whereas other families that don’t communicate well, that don’t present their children with unconditional love and acceptance, will be guessers. This is due to the parents inability to establish and maintain boundaries, or interact when problems arise with emotional stability. The children of guessers then have to use outside clues to figure out how to get what they need without directly asking for it, because they don’t just fear rejection, but retaliation for having asked.

This very much relates to relationship attachment styles. If you’re a secure attachment, you’re probably an asker. Whereas if you’re an insecure attachment, you’re probably a guesser.

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