The Disappointments

Ray, James and Gary, three close friends in their late 50s/early 60s, are rocked by the suicide of a friend from their past.

Ray, James and Gary deal with the fallout from a friend's suicide. Dwight offers to move in with Ray to help him pay his bills.

Dwight puts Ray on a budget. Gary, James and Ray go to an Open House.

Ray sticks up for Dwight and later learns that Keith's body is still in the morgue. James uncovers the the secret that Gary has been hiding from them all.

Ray, Dwight, Gary and James go to a memorial.

Exciting new opportunities arise for Ray, Gary and James while Ray finds himself fixated on his ex, Dwight.

Ray's preoccupation with Dwight gets him in trouble back at the writers' room, while James takes on his first open house and gets an unlikely new real estate client. Meanwhile, Gary gets some action on his dating app.

Ray, Gary and James go on dates.

Ray continues to be an outsider in the writers' room while Gary makes a troubling discovery about Lorena. James reluctantly allows Ray to ride along when he insists on going with James to see Phillip's house.

Ray's past comes back to haunt him.

Gary and Lorena go on a shopping spree while James deals with a complication at a client's final walk-through. Ray learns that his writing contract isn't going to be picked up and is devastated by Dwight's big news.

James and Gary make a surprising realization. Ray puts his heart on the line.

Ray attempts a coup at the office. James loses a client. Gary and Lorena shoot their talk show pilot.