In the aftermath of Jackie's affair going public, Jackie and Anders separate and consider their options. Anders' feelings for Brenda complicate the idea of continuing the marriage, but pressure from his parents makes it hard not to reconcile with Jackie.

Jackie and Anders throw Rolly a welcome home party that ends in disaster when Jackie's affair with Steven is revealed. Meanwhile, Falcon introduces Bree to his old friends, and Kenneth finds unexpected romance with the catering director of the event.

After Brenda and Anders share a heat of the moment kiss in DC, Anders struggles with his feelings for both her and Jackie and we learn the backstory of how Anders and Jackie reconnected after high school.

The filmmaker follows Jackie and Caroline in their high school and present day years, revealing what caused them to end up in such different places than planned.

Anders encourages Jackie to make an effort to be nice to Dawn considering she is his best friend's wife, and when she finally forces herself to visit, she find Dawn in labor and rushes her to the hospital.

Brenda and Anders see each other for the first time in ten years and explore the reasons they broke up. Steven travels to New York City to see Falcon, and discovers Falcon has a wife with whom he is separated.

Steven finds his footing as father to his 9-year-old son, while Dawn opens up about her family. Meanwhile, Rolly, in Afghanistan, misses the big moments in Dawn's pregnancy.

A documentary crew follows a disparate group of high school seniors from Greenbelt High School's class of 2000 in Austin, TX as they prepare for graduation, and revisits these former classmates ten years later in 2010 to see where they are now, what they've become, and where they're still headed.