I disagree with charliehall about “wear something that makes you comfortable.” If in your picture on SYAS you were wearing Shabbos clothing and makeup, you need to wear that on the first date. G-d Willing there will be a second date and then you can wear comfortable clothing. He will be checking to see if your picture was “enhanced” -and you should do the same.
And yes, it is totally normal to meet in a hotel lobby and talk.
I would agree with charlihall about being honest, but you don’t need to answer every question you are asked. My rule of thumb is don’t ask or answer anything you wouldn’t want on page 1 of The New York Times on a first date. Feel free to change the subject.
Ask him to describe what Shabbos afternoon is like on a long summer Shabbos or what Saturday night is like on a short winter Shabbos. Ask him about all of his siblings and tell him about all of yours. The point of the conversation is to try and determine whether shy means he is emotionally unavailable. If you smile and are careful to be non-threatening, will he open up and tell you the things that his casual acquaintances know about him?