At least the jobless friend has some sort of "excuse" for not having $$ - he has no excuse for tagging along and expecting others to pay his tab.

I used to socialize with a couple who would order the cheapest item on the menu (and pay for it) but expected to "share" others' food items.

I don't socialize with them anymore - a friend is one who can reciprocate in some way, and money is the least of it, watering someone's plants etc. when your buddy is out of town for example is a way to meet one's social obligations if $$ is an issue for one party.