'Round the Square is an ensemble piece focusing on six fictional characters who live and work in and around Portsmouth. In the pilot season, Cheryl, is losing both her store and her apartment. Evan, is also worried about losing his apartment and takes in an old college friend, Jack. Unfortunately for Evan, Jack has grown up since college and the two find it difficult to be roommates again. Andrea, is worried she's sacrificing her life for fitness. She's obsessed with exercising and doesn't realize it until her new boyfriend points it out. Nate, is the group's "Go-to-guy," but his status gets challenged from an unlikely source: The quirky Emily, who lives life by her own terms and tells people how it is... or at least how it is the way she sees it.. 'Round the Square captures the spirit of America's favorite little port city. Cheryl and Nate own their own businesses. Cheryl owns a bead store, Nate is a contractor. Andrea is a personal trainer and can always be seen running around ...