After Oscar and Felix become obsessed with eavesdropping on their bickering neighbors, they try to subtly intervene and help them save their marriage. Meanwhile, Emily and Dani's friendship is tested when they train together to race to the top of the Empire State Building.

Oscar faces a personal dilemma when he dates a young nanny, Allyson, who works for his neighbor, Charlotte. Also, Emily forces Felix to participate in an activity she's interested in, for a change.

Oscar's dream comes true when he is asked to throw out the first pitch at a New York Mets game. Also, Felix surprises Oscar and invites his father to be there for the big day.

Oscar attempts to impress Charlotte by purchasing a table for a fundraiser to benefit The New York Philharmonic. At the event, Felix reminds Oscar about the importance of being honest and Teddy introduces his wife, Diane, to Dani for the first time.

Oscar and Charlotte hit a speed bump when they hesitate to take their relationship to the next level. Also, Felix attempts to overcome his fear of dogs with Teddy's help when Emily regains custody of Biscuit.

Oscar reluctantly agrees with his agent that it’s time to shake things up on his radio show and allows Dani to have a bigger role after a rival host, Rich Eisen, taunts him. Also, Felix is eager to meet Emily’s mother, Judy (Joanna Cassidy), but things don’t go as well as he hoped.

Felix attempts to reverse Emily's birthday curse and plans a nice dinner to celebrate with friends. Also, Oscar and Charlotte face another obstacle in their relationship when Oscar meets Charlotte's son, Evan (Caleb Brown).

Oscar learns that Felix was nationally ranked chess player as a child and convinces him to return to the game to make money. Also, Emily investigates why Felix is acting strange since he began playing chess again,

Felix forces Oscar and Emily to go on a date to get to know each other better in the hope that they’ll become friends. Also, Teddy agrees to help Dani with her first contract negotiation.

In an attempt to surprise Emily, Felix gets his learner’s permit and enlists his friends to help him learn how to drive. Also, Oscar is annoyed that Felix doesn’t ask him for help,

Oscar and Felix run a heated campaign for president of their building’s tenants’ association, but Oscar doesn’t fully realize everything the position entails.

After Murph persuades Oscar to try online dating, Oscar finds himself on a blind date with Felix’s ex-wife, Ashley.