Robert and Lily, two star-crossed lovers from very different worlds who would probably never meet under normal circumstances, are thrust into a support group for survivors of sleeping attempts which soon changes their lives forever.

In the wake of the loss of one of the group members, Lily takes some drastic steps to change her life. Similarly, Carla finds herself inspired to shake things up in her ordered domestic existence.

As Lily and Miller begin to form a more personal relationship, her dream of having her own vintage clothing boutique is becoming a reality. Jorge decides to try his hand at stand up comedy.

Robert and Miller begin a strange friendship while trying to find Lily, who doesn't show up at the support group meeting. Dogg arranges for the group to help at a senior center.

Robert begins to come to terms with the loss of his wife hoping to make room in his heart and his life for Lily. Group members Adam and Shawna flirt despite the difference in their ages.

Dogg decides to stop taking his meds, which proves to be a challenge for him when the group competes in a Recovery League softball tournament. Lily takes Robert to a funeral.

Robert takes Lily on a picnic in Central Park. It is the perfect date until the weather turns. sending them seeking shelter. All the while, Miller is watching and pulling strings.

Robert and Miller's relationship hits a stumbling block. Miller turns to Lily, revealing a personal secret from his past that informs who he has become. Robert takes Lily to dinner at his mom's house.

Carla celebrates two years since her sleeping attempt with her husband and the support group. Jorge celebrates his recently enlarged penis by taking several comedy club waitresses for a test drive. Robert and Lily seemingly have overcome all of the obstacles in their way, allowing them to truly let themselves fall in love with one another. And finally, Miller suffers a panic attack after his colonoscopy. He has criminals on his tail due to his gambling debts, but all that matters to him is the important piece of evidence he needs to solve his own personal puzzle.

The season finale begins with many of our characters believing they have exactly what they want and need. Adam and Shawna have each other. Carla and her husband Ralph have each other. Robert and Lily have each other. Lily also has the grand opening of her vintage clothing store. Jorge has a huge penis. And Miller has evidence that allows him to finally confront the man he believes is responsible for the greatest tragedy of his life. Much of this will be upended when unexpected tragedy strikes, regrettable words are spoken and Lily, Robert and Miller all find themselves on a collision course with a destiny none of them could have imagined.