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Suspecting her husband of infidelity, gynecologist Dr. Catherine Stewart hires an escort named Chloe in order to test his faithfulness. Soon, the relationships between all three intensify.

A first-year law student at Harvard Law School struggles with balancing his coursework and a woman, unaware that she has a connection that affects their relationship.

On the last day of school, the Coyne twins throw a party at their mansion to celebrate graduation and the end of another school year. Spinner finds out, overhearing Holly J. and Jane talk in the changing room, that Jane had an affair with Declan a few months ago. Furious and distraught, he breaks up with Jane in front of everybody. He comes back to the Dot to find out that Emma accidentally caused it to blow up in flames. Meanwhile, Holly J. and Declan commence their summer of love with Fiona and Jane tagging along. Holly J. finds out the hard way, unfortunately, that there's only room for one woman in Declan's life: his sister. Will rivalry end the summer of love? In an attempt to cheer up Spinner, Manny, Jay, and Emma take him to a casino where, after a drink too many, Spinner and Emma wake up in a hotel room...married à la Las Vegas. Spinner and Emma decide not to have an annulment and throw together another wedding in front of all their family and friends. Jane desperately tries to crash the wedding and Holly clings onto Declan any way she possibly can.