Nora and Steven have differing opinions about Annie's new boyfriend, Kevin. Steven, thrilled to have another guy at the Bernstein-Flynn brunches, tries to talk Annie into keeping Kevin around, while Nora, who finds Kevin incredibly annoying, does everything in her power to convince Annie to dump him. That is, until Annie catches on, and pulls a fast one on both of them.

While Bess tries to hide the fact that she's a parent from her new old-fashioned boss, Vince, Nora has to endure her family's less-than-enthusiastic response to the news that Elliot is back in her life -- until she gets a little unexpected help from Steven.

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.