Bess and Steven hire a nanny to take of Charlie for the holidays. But they're very surprised when the nanny turns out to be a 45 year-old man. Terry is a wonderful nanny, but Steven and Bess are embarrassed to tell people that he's the nanny, so they start to come up with fake stories for a reason why he's helping with Charlie, until Terry finds out and quits. Meanwhile, Annie and Gordon go on their first real date. But Annie keeps blowing Gordon's plans for more spontaneous things, until he surprises her with a romantic dinner.