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.