BP Totty: I agree that special occasions call for special treatment. But if a first date is a first step in the direction of the chupah – which it is – it is not a time for “putting on the ritz.” It is a time for a prospective chosson and kallah to start getting to know each other.
Willi: if you are the “girl” in the story, you ought to ask yourself whether you are wasting your date’s time. As you said, you felt bad and figured he must be penniless, but you still found it very odd. Dating for the frum is not a lark or a hoot – it is serious business, and if you think the prospective date is odd, you owe it to yourself, the date, and Hashem to say no and wait for a date you can take seriously. And your statement that you did not know that the return trip would also be by train show that you are not particularly astute, nor did you have the sense -and decency – to ask. I have the feeling that you regard this date as one big yuck with a strange, if not penniless, man. He might be neither, but neither you nor the readers of your story will ever know.