Hello, it is a romantic comedy movie.
it starts with a wealthy man who declared his engagement to a woman in some fancy party. But one day this man lost all his money and his fiance damped him because he was broke.
Although, this man is deeply in love with this women even after she dumped him when he was broke. He find that his girlfriend has a sister that she doesn’t talk to her because she knows what her sister is really is (a gold digger).
So the man goes to his girlfriend’s sister and ask her to help him win back her sister.
the sister agrees to help him based on some rules, for example the man should never fall in love with her and some other rules.
in the process of helping the man, this man accidentally falls in love with her but keeps it a secret. after teaching him what her sister loves in mans, who man is ready to meet back his ex-girlfriend, where he wears a nice suit and rent a limo and takes her to a fancy dinner.
Although, in the middle of the middle of the dinner he realize that he doesn’t love her anymore and runs back to her sister who helped him, and finds her if im not mistaken in a restaurant or a bar alone, through a window, and tells her what he feels about her.
The movie is an american movie i think it is an Brooklyn or Manhattan or New-York or something like this, between i think 1998 and 2007, and i think that the sister use to love painting arts in some underground subway, it is NOT white and black movie, and i seen it on TV.