Summer is over and the hot mess express has rolled back into town. Thomas has full custody of his two children and has risen to the challenge of being a single dad, by mostly giving up his former playboy lifestyle. Shep, however continues to be Charleston's perennial bachelor and now, thanks to Craig's lying ways, has a new wingman, Austen. Not only does Austen look like a younger version of Shep, he's also giving him a run for his money with the ladies. Cameran, meanwhile, is still determined to see Shep settle down and is convinced she knows just the girl who can reel him in. On the other side of town Landon, who after fleeing the rumors unleashed by Kathryn's accusations, is back in Charleston with a new boyfriend and determined to turn her travel website, into a success. Meanwhile, after a stint in rehab over the summer Kathryn has returned, and according to Thomas, refusing to take a drug test. Or is she?

Craig attempts to "adult" by helping Naomie throw a fundraiser, but the differences in their planning styles threatens to expose the cracks in their relationship. Meanwhile, Kathryn takes steps to become more responsible, just as Thomas decides it's time to rekindle his friendship with Landon. Later, it seems that Cameran's matchmaking skills are finally paying off after Shep and Chelsea share a romantic evening together. But when Shep leaves town without making his intentions known, Austen swoops in to take his place.