I RAISED THAT BOOOOY (Who are you?)
He finally got it. He's confident and now capable of building pleasant rapport during a date, making him someone relatable and more importantly fun to talk to. Instead of going over his interview like questions, he's just going with the flow and say whatever random thing like with the cow stomaches and he even had fun teasing her about it.
And bonus point, since he's still new at this, he's not at all jaded and could show genuine emotion, making the handholding moment (and I suppose the night) kinda sweet.
Though he really didn't expect he was already charismatic enough to have a cute waitress hit on him without having to do anything but be a regular.