First, he started his narration when he met her again at the play; in that moment he did not seemhappy to see her. He remembered he first time they met, for him it was not a good time, eat in fancy restaurants were not an optionfor him but he still asked her out. Something, I see in the story, is the fact that she never gave him the opportunity to talk, she wasa little selfish by ordering all the expensive stuff in the menu, without consideration of his economical situation.
On theother hand, he was not clear with her at the beginning when he wrote her a letter, I think, he should tell her the truth and took her toa cheaper place, avoiding the unpleasant situation, and probably he could had the opportunity to meet her better and have goodmemories of that time.
Finally, I think that men try to be nice and gentleman when they had the chance to date a woman and that attentionis always good. Nevertheless, there are other ways to have a good time without spending a lot of money and they can be also gentlemen.