Closed questions bias the conversation in addition to making it clumsy.

Doctors try to maximize the information they get from a patient by using open questions. Only after it's clear what the complaint is, they make precision strikes with closed questions. It's very easy to bias the patient and get a wrong diagnosis if you're not careful.

I suppose in a casual setting the bias will be even greater because the other person is deliberately gauging what kinds of things you would be pleased to hear based on your questions.