Andi and Bobby are a happily married couple with one child and another one on the way, but they fondly remember the time when they had less responsibility. Will is newly single but pines for his ex-wife. Jules and Lowell are in a passionate new relationship, and Jules' friend Kate is upset to learn the last of her remaining single friends is now engaged.

The group of six friends in this romantic comedy are all at different stages of their lives: married, divorced, engaged, and single. They are all reasonably happy with where they are at, but secretly wonder if their friends actually have it better than they do.