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.
When Caroline finally agrees to meet Del's mother whom she's been avoiding cause she hears that his mother is a difficult person. So she goes to Remo's but Del gets stuck in the subway. And when Caroline sees a woman who's acting like a hag, she decides to wait for Del to arrive but she can't avoid her cause she goes all around complaining. And Annie learns that it's Richard's birthday and she tries to get him to celebrate it.
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.