Bridget and Paul are surprised to find themselves in similar situations when they are both alienated in their social circles. But they devise a plan to settle the score, leading Paul to crash a poker game with Tommy to get closer to boss Nick, and Bridget trying to break up ex-boyfriend Kyle and her nemesis Jenna.

Cate sends Bridget and Kerry to their grandmother's house for a visit after the Hennessys decide against vacationing at the family cabin. But while on their road trip to grandma's, the girls are shocked to find Cate at their father's favorite saloon with a mysterious stranger. Meanwhile, Kerry makes Rory's life miserable when she discovers that he has a crush on her friend, Rachel.