Group leader Dogg decides to stop taking his meds. This proves to be a challenge for him when the group competes in a recovery league softball tournament, triggering old issues for the former big league ball player. Also, Lily takes Robert to a funeral, creating questions in Robert's mind about Lily's emotional life. Meanwhile, Miller visits a doctor as he believes he may be confronting a serious medical condition.

Miller and Robert attend yoga and have their pictures taken together in a photo booth, prompting Robert to worry a bit about how this “bromance” is evolving. Robert then picks Lily up and takes her on a picnic in Central Park. It is the perfect date until the weather turns, sending them seeking shelter in a tattoo parlor and a storefront psychic shop. All the while, Miller is watching and pulling strings, clearly gathering evidence and interfering in Robert and Lily’s lives at the same time.

Carla celebrates two years since her suicide 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.