The Upper Hand S06E01 - Moonlighting

When he cannot pay a restaurant bill and needs Caroline to help out Charlie feels he is a kept man in the eyes of her friends so,to impress,he buys her a painting at a charity auction even though he cannot afford it. To make up the money he takes work as a topless waiter but his initial embarrassment at being groped by women gets worse when Jo is one of his customers. Ultimately he has to swallow his pride and agree to Caroline lending him the money for her painting.