Casey and Cappie are working together in their clothing business called Caspie Creations. Cappie is the playboy boss, flirting with every one of his assistants and the girls that work under him. Rebecca is now Casey and Ashleigh's best friend, and marrying Evan Chambers. Calvin is still gay, and with Michael, but he might be having feelings for one of his girlfriends. Heath is back from his year in Europe. Cappie meets a new girl and he forgets his playboy ways. Cappie takes a turn in his life and gets engaged. Rusty is hiding his relationship with Jen K. from everyone and the truth is going to come out. Frannie falls for the Beaver, now known as Charles. Old flames are going to come back, and drama is going to start in Chicago again.
Scott Michael Foster…….Cappie
Spencer Grammer…….Casey Cartwright
Amber Stevens…….Ashleigh
Dilshad Vadsaria…….Rebecca Logan
Jacob Zachar …….Rusty Cartwright
Jessica Rose…….Jen K.
Jake McDorman…….Evan Chambers
Paul James…….Calvin Owens
Aaron Hill…….Beaver "Charles"
Clark Duke…….Dale
Tiffany Dupont…….Frannie
Zack Lively…….Heath
Chase Crawford…….Damien Johnson
Amber Tamblyn…….Alexandra "Lexi" Thompson