he would also horn in on "hanging out" with his [broke, underpaid] employees] when we went out for beers and food after work. he would order food and drinks and then "realize" he forgot his wallet and we would have to cover his share of the bill

Instantly reminded me of

The girl at the counter was very nice about it and professional, and was like “Sir, you need to pay for those first.” At first he kept pretending to be tired and not hear her, but eventually turned back around and brought them to the counter.