When a big client shows signs of leaving Hale Dayton, Alex (Hank Azaria) 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 (Mo Mandel) and Gregg (Al Madrigal) for assistance and things don't go exactly as planned. Meanwhile, Emma (Natasha Leggero) has set her sights on Andrew (John Brotherton, Dexter), who works upstairs in the building. With the help of Helen (Kathryn Hahn) and Walter (Joe Lo Truglio), she tries to turn on the charm. Anthony Head also stars.