Jack sets up a double date to get Eddie out of a post-divorce rut, but the night gets awkward when they run into Denise, Eddie's ex-wife. Also, when Emma decides to breakup with her boyfriend, Greg, Clark is torn between making a move on her and salvaging his friendship with Greg.

At the magazine's notoriously carnal company retreat, feelings resurface between Jack and Brooke as they work together to help Clark finally hook up with Emma – the same way they did five years ago. Also, Roland asks Jack to lead the staff in his absence after he accepts a once-in-a-lifetime opportunity to return to field reporting.