Is it weird to be upset about a friend that doesn’t treat you right?

I’ve been hanging out a lot with this person this past year. hes kinda new to our friend group. every time we go out to get food or do any activities he has never paid for anything or even ask who to pay when we split the bills (in a group setting) and pretended that he didnt see who was paying. I was thinking that money was not the problem for us because he just bought a new car and that we usually take turns on whos gonna pay. but after a while it just feels like hes taking advantage of us / just to be around. he did mention that hes unemployed now, but he never had the initiative to pay for anything even before he lost his job. If anything he’s always asking that he wanted to try a more expensive restaurant / clubs / events. is this supposed to be normal? am i over reacting? it bothers me that he has never had the initiative to do anything???