willi, reference to you being married before i think was to point out that this wasn’t a very young bochur who should have known better.
NO, I don’t think it is proper to take a train late at night even if HE likes to. If he likes to ride the train he should amuse himself at any other time, not when he is on his first date with an experienced woman. Secondly, if he takes you all the way to the city he should have at least taken you for desert and offered you a little more than a bottle of water. “Can I get you a drink? Soda, juice, water, etc?” It is awfully strange to offer someone just water. Taking it home with him is equally strange unless he asks you, would you like to take that for the train ride home.
And again, a train ride if agreed upon would be OK for a day date but not for a night time date. In addition, as someone else mentioned, it is not mentchlich to not pick you up before the date nor walk you home after. This is quite selfish and shows he was only thinking about his own convenience the entire night. I don’t think it has anything to do with being poor. Cheap and stingy is more like it. Poor people still have manners.