person A: I go out with one of my friend. This friend is so cheap that he doesn't to pay for anything. He even once embarrassed me in a bar.
person B: That sounds frustrating_comma_ especially if they are inconsiderate and drain you of your funds. They sound kind of entitled.
person A: He asked the barman if he can bring his drinks from home. I was so embarrassed.
person B: Oh wow_comma_ that must be embarrassing to deal with. Sounds like they are going through a financial situation_comma_ but they should at least talk to you about it since you two are friends.