*See my prev. comment in a same comment branch.
I have similar experience being with my close friends who don't make a lot of money. We never go to expensive restaurants or expensive places. If we get together and I think the bill will be high, I just cover for myself, my gf and person in the group who makes the least. That pretty much covers 75% of the bill. My friends are OK with that, because they know, I always there for them and never will use it as point of leverage or being show off.