Oscar's life seems almost perfect...sure he's divorced and his apartment is a mess, but he's the host of a well-known sports show, and is enjoying his bachelor lifestyle in New York City. That is until his college friend, Felix, shows up at Oscar's apartment having just been dumped by his wife. Oscar does his best to console his old buddy and get him back on the dating horse, but his attempts uncover just how unresolved his own feelings are about his ex.
In the third season opener, Oscar is forced to choose between his romantic plans with Charlotte and helping to save Felix's relationship as Emily decides to extend her stay in London and Felix starts to fall apart.
When the IRS decides to audit Oscar and his ex-wife Gaby, Felix offers to mediate between the contentious exes when he realizes that he might be the reason Oscar was audited in the first place.
Oscar tries to outsmart his nemesis, Rich Eisen, after he is forced to present him with a humanitarian award. Also, Felix experiences a range of emotions when he sees Emily at a restaurant.
Oscar and Felix seek the advice of a counselor in their apartment building to help overcome their issues. Also, Oscar's opinions on relationships, combined with Felix's meddling, complicates matters for all of their friends.
Oscar reconnects with many significant people from his father's life when he agrees to carry out Walter's last request to spread his ashes behind the candy factory he once owned.
When Oscar feels threatened by Felix’s surprising performance on the softball field and basketball court, they agree to a decathlon to determine which one of them is the better athlete.
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.
Felix meets a fun-loving woman, Natasha, in a bar and takes her home for what is meant to be a one-night stand, and Oscar takes things to the next level with Charlotte.
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).
When Oscar and Felix make a trip to Ashley's to retrieve Felix's special pillow, a secret that he has kept from Oscar is revealed.
Oscar sets out to prove to Charlotte how he's capable of being responsible when he volunteers to take her son Evan (Caleb Brown) trick-or-treating on Halloween, while Felix celebrates the holiday by leading the kids in their building on a haunted history tour.
With the help of Murph, Oscar decides to throw a big party when Felix finally agrees to spend the weekend away. Also, Felix and Emily have their first sleepover.
When Oscar and Felix attend the wedding of an old college friend, Oscar aims to reconnect with an old flame while Felix is determined to show his ex-wife that he’s a changed man.
After Oscar and Felix become obsessed with eavesdropping on their bickering neighbors, they try to subtly intervene and help them save their marriage. Also, Emily and Dani's friendship is tested when they train together to race to the top of the Empire State Building.
Oscar rashly enlists Felix to help him save his favorite hangout, which is in financial trouble. But ends up regretting asking for that favor from his roommate when Felix tries to put his stamp on the restaurant.
After a heated argument, Oscar and Felix decide it might be best to change their living arrangements and find new roommates.
When Felix substitute teaches a yoga class, his teaching style rubs everyone, including Emily, the wrong way. Also, Oscar and Dani get trapped on a subway car, adding to their frustration about living in the city, and Murph asks Teddy to be his agent when he’s approached to be the spokesperson for a Norwegian health supplement.
Felix goes into a frenzy when the responsibility of hosting the Unger family Christmas falls onto his plate after his perfectionist mother bows out. Meanwhile, Oscar tries to convince his roomie's mom to give her son a break.
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.
Dani's excitement at being promoted is cut short when Oscar tasks her with the daunting job of hiring her own replacement. Also, Felix tries to plan the perfect surprise after Emily admits she misses England.
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 becomes obsessed with living up to Murph's standards when he finds out the girl he is seeing used to date the handsome ex-baseball player. Also, when Emily volunteers to be a part of a historical reenactment on Ellis Island in order to spend more time with Felix, he is too busy preparing for his role to pay any attention to her.
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.
After Murph persuades Oscar to try online dating, Oscar finds himself on a blind date with Felix’s ex-wife, Ashley (Christine Woods).
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.
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