You are interpreting “shy” as a fixed character trait rather than a situational one. Many people who are not ordinarily shy-acting are shy when it comes to asking someone something personal in front of a group of friends and acquaintances.
There was nothing that forced the guy in that interaction to start the interaction by asking something personal.
He could have started interacting with her by making harmless small talk.
You are interpreting “shy” as a fixed character trait rather than a situational one. Many people who are not ordinarily shy-acting are shy when it comes to asking someone something personal in front of a group of friends and acquaintances.
There was nothing that forced the guy in that interaction to start the interaction by asking something personal. He could have started interacting with her by making harmless small talk.
What it means to be shy is that someone is bad at doing small talk.