Witches VS Patriarchy

They opened themselves up to a conversation about it,

If the question to "name 5 songs" is an attempt at opening up a conversation, it's a questionable strategy. You're not making conversation, you're assigning someone a test. Forcing a set list provides plenty of opportunity for the answers to be scrutinized and possibly used as justification to doubt the woman's authenticity. It's a commonly used gate-keeping tactic that most, if not all women and AFAB have/had used against them at some point.

A friendly acknowledgement of a shared interest would work far better, like going, "Oh, I love that band! Did you go to their last concert?" Even, "What's your favorite song?" works, because the problem isn't asking a question, but the immediate assignment of work along with guaranteed judgement regardless of the answer.

Most people probably don't enjoy being subjected to pop quizzes, and this kind of question feels like being given a pop quiz with the sole reward for winning being "to be accepted by you." Even if one's intent is truly innocent, when someone's idea of "conversation" is "subject the other person to random tests," other people might avoid interacting with that person.