Shared history is a reason to listen carefully, not a reason to stop asking.

Long acquaintance builds a model of a person, and the model gradually gets consulted instead of the person. You know what they think about work, what they will order, how they feel about their sister, and much of it was accurate five years ago. Knowing someone well should make your questions better, not fewer. The people most likely to be out of date about you are the ones who have known you longest.

Ask someone close to you something you assume you already know the answer to. Let them surprise you rather than correcting them back into your version.