Alex is suffering from post-divorce trauma. Helen has yet to recover from the death of her fiancé. The two coworkers end up in an awkward dating situation that neither are prepared to solve.
Stephen asks Alex to entertain a client who is thinking of leaving and when he needs to find female companionship, he turns to Dan. Emma has a thing for a man who works in another office and Helen tries to help her.
Stephen assigns Emma to help Alex and his team on a presentation after she speaks out of turn in a meeting as a way to not so subtly push Alex. Helen visits Alex's therapist, then ends up on a date with him.
The team is assigned to help a client who cheated on his wife. Alex's office mates attempt to assist with his love live by creating a fancy online profile for him.
Alex decides to emulate Dan's methods as it applies to picking up women. Helen is tired of staying home alone so tags along with Emma after work.
Helen is terrified at the prospect of being a Godmother. Stephen directs his staff to poach clients at a funeral of a recently deceased competitor.
Alex obsesses about out-doing his ex-wife's new boyfriend to impress his kids. Helen is put in charge of the public image of Stephen's latest very young squeeze.
Helen works on a campaign to make Oregon raisins more sexy while Alex strikes up a relationship with a woman in his building.