Jim tries to stop eating junk food and is then faced with his greatest challenge: a child's birthday cake. A hungover Dave goes with Jim to a kid's birthday party where unbeknownst to him, he is mistaken as a homeless man.
Jim plans a romantic anniversary that includes a Broadway show and stay at The Plaza hotel. The night is interrupted by visits from Daniel, Dave, Dave’s girlfriend and her jealous ex. Not quite the anniversary Jim had planned.
Jim and Jeannie help Daniel deal with the tension between him and his father by having dinner with the two of them. Later, Dave joins the group for a crazy night out.
Jim has finally been asked to do “The Tonight Show with Jimmy Fallon.” Jeannie, trying to make a friendship happen between Jim and their Priest Father Nicholas, invites him to tag along. An already nervous Jim is not pleased.
During a scary storm, Jim consoles his children by telling them a story from his own childhood and in the process learns an important lesson about his past.