Caroline advertises for a colourist and employs Richard. Her former boyfriend, Del, has moved on and Caroline is under pressure to also get a date. Richard steps in at the last moment to allow Caroline to save face in front of Del.
Richard is mugged and Caroline helps him by buying him a new wallet. On the return journey, he and Caroline catch the mugger and he is arrested. The mugger turns out to be a small guy and Richard thinks of himself as a bit of a wimp.
Caroline manages to get Richard's work displayed at an art gallery. They later find out it only shows works by gay artists. When Richard hears that the painting could sell for $20 000, he pretends that he is gay.
Caroline picks at her nose in front of the camera at a malfunctioning ATM and is embarrassed to ask the manager for the money it didn't dispense. Richard is having a lot of difficulty breaking up with his girlfriend, Shelly.
Caroline finally agrees to meet Del's mother whom she's been avoiding because she thinks that his mother is a difficult person. She arrives at Remo's Ristaurante, but Del is stuck on the subway and hasn't yet arrived. Caroline spots a haggish woman and mistakes her for Del's mom. Intimidated, she hides out in the kitchen until Del arrives. Annie discovers that Richard is spending his birthday alone and she tries to help him celebrate.
Caroline's auntie, Mary, arrives for a visit and sets her up with a date. Caroline takes him to the opera when Del doesn't want to go, which makes Del very jealous. He resorts to extreme actions to win her back.
Caroline and Del are try going for a holiday vacation together but all they do is break up. Caroline wants revenge. Richard tries to break up with Shelly by getting Charlie to take her out. Things don't go as planned.