[It’s fine! There’s really no such thing as a bad ask now is there?}
If he knew they were shy, he would go about slightly more discreet ways to confess to them, sending them cards here and there, nothing too extravagant. He would also be patient when talking to them, willing to help egg them on if that’s what it meant to get them to talk more to him. He would never force them into situations that they might not want to be in.
He would be a bit less patient, not understanding why they wanted to stay so secluded but since he did like them, he would teach himself to be nicer. He would always initiate the conversation for them and sometimes he even did the talking for them! Once he asked them out, it would be somewhere where there weren’t many people as not to embarrass them.
He would always smile at them and wave hi, running over to go talk to them. He would make sure that they always had room to talk and add in their opinions and listen intently when they talked. He probably would have accidentally let his feelings about them slip during a conversation and would have them blushing furiously.
He would talk to them and would back off when they seemed a bit nervous, not wanting to intimidate them in fear that their feelings may become negative towards him. He liked to talk to them and would tell them that he valued their opinion and wouldn’t mind if they talked passionately about something, probably finding out what it would be to make them talk more. He would ask them out via note, something a bit secretive.
He knows nothing about being subtle. He would always run up to them loudly, yelling their name to get their attention. It wouldn’t be until they told him to back off that he would realize he had been doing this wrong the entire time, finding them to confess that he only did that because he liked them. He would work around the shy thing, trying to make them more outgoing if they let him.