He always gets me to pay...

I am a 24-year old woman and have been dating a 27-year old guy. We have known each other since college and have been working since then. He gets paid a little more than I do, but always ends up asking me to pick up the bill when we go out, because he says he has a lot of responsibilities at home. I used to agree at first because I know his family is not well-off, but I sometimes get the feeling that he is just using me for my money. He is like this with his friends, too, always asking them to pay and saying he doesn’t have enough. They don’t resent it, or probably don’t show it, but it’s getting on my nerves now because I don’t want to feel this way. I can’t speak to him about this because it will embarrass him and I don’t want to damage our relationship, but it can’t go on like this either. What should I do?
If you can’t have that conversation, is this relationship really working? If you feel strongly about something and can’t express it, what makes you believe this is going to get better? Tell him why you don’t like it and give him an opportunity to change. It is also feedback that is good for him, so you aren’t being a problem here. Not speaking about it isn’t going to help after a point because the resentment you feel will only get worse. Why not nip this in the bud or, at the very least, find out if he genuinely wants to do what it takes to strengthen this relationship?

My friend was not well for a while, and is better now, but constantly uses her health as an excuse to get sympathy from everyone. How do I get her to stop doing this?
You can tell her why you feel the way you do, because that is what friendship is about. Honesty is a virtue between friends, so why not speak up?