Newly-divorced Alex is missing his kids and trying to keep himself together. Alex's co-worker Helen thinks she has it together, but she drinks too much in order to cope with her fiancé's untimely death. It's no surprise then, when these two overworked public relations executives share an ill-fated night of passion and are forced to cope with the awkward aftermath.
When a big client shows signs of leaving Hale Dayton, Alex is charged with taking him out for an evening of entertainment. But when Alex realizes he's still a bit rusty with women, he calls in Dan and Gregg for assistance and things don't go exactly as planned. Meanwhile, Emma has set her sights on Andrew, who works upstairs in the building. With the help of Helen and Walter, she tries to turn on the charm.
When a client is amused by Emma's outspoken irreverence in a meeting, Stephen decides she must help with the big campaign pitch presentation. As Emma immerses herself in the preparation, commandeering the staff and the conference room, Alex struggles to deal with the unpleasant development. Meanwhile, Helen takes Alex's advice to visit his therapist, the handsome Dr. Hu, but she finds herself thinking she would rather date him than see him professionally.
When longtime Hale Dayton client Fred Potter, is caught in an extra-marital tryst, the team sets to work on damage control. As Stephen and Helen mastermind the response for the client, Dan, Gregg and Emma help Helen in a rebranding campaign of another sort, setting Alex up with a slick online profile and a cute new date.
When the Hale Dayton team hits the bars to do research for a new sherry campaign, Alex is frustrated by Dan's effortless success with women and decides he needs to adjust his approach. Meanwhile, Helen decides she should try to get out more and starts socializing with Emma and her friends after work - but the late nights prove tough to take after a while.