In Remo's Richard is trying to tell the owner a joke to work on his people skills. He's meeting a member of the arts council about doing a mural. When the man, Tom, arrives he tells Richard he's one of three being considered. Caroline and Annie come in for some takeaway food and Annie decides to annoy Richard. The two women introduce themselves to Tom who says he loves Caroline's cartoon. When the women leaves Tom tells Richard if he tells him Caroline's phone number it'll help his bid, which Richard does.
Before the date Richard is grateful but Caroline is quite happy to go with Tom. Outside Tom and Caroline meet Del and Charlie and after an awkward meeting Del confronts Richard in Remo's about setting her up with someone else. Remo and his waiter back Del up that a guy is supposed to have a couple of chances at a reconciliation first.
Caroline gets home at 2:30am and Richard is in her apartment waiting for her, angry that Tom can't consider his request to do the mural if he doesn't have sleep. Caroline tells him Tom is going to recommend him and he just needs to take in a couple of sketches. She surprises Richard by saying she is going out with him again.
Richard takes the sketches to Tom's office the next day and the receptionist tells him he's with his wife. Richard tries to leave but Tom catches him and thanks him for Caroline's phone number. Richard tries to put Tom off her by saying she takes drugs and drinks but Tom says he thinks Richard is a definite for the mural. Richard leaves but feels very guilty.
Caroline is preparing her special dish for Tom and Del runs to meet Annie while she's getting ready to go on stage to ask her about it. Annie points out that they're not dating any more but Del is still jealous. At Caroline's flat things get comfortable and Caroline and Tom start making out. Back at the theater Richard arrives to tell Annie that Tom's married and tries to persuade her and Del to tell Caroline.
Back at Caroline's apartment Tom tells her himself that he's married and she kicks him out. As he's leaving Richard turns up and throws Tom's coat in the hall and tells Caroline. When she tells him she already knew Richard picks up the coat and tries to salvage his chances but Tom tells him he has no chance at the mural anymore. Del also arrives to tell Caroline about Tom and then Annie runs in, still in costume, then runs back out again when she sees Tom's not there because she's due back on stage.
Caroline thanks Richard for warning her about Tom when it lost him the mural but doesn't thank Del because he would be happy that her first date after he dumped her was a disaster. Richard, who is looking out the window, describes Annie dragging Tom from a cab and throwing him onto the street.
