Michael is a young architect, deeply in love with his girlfriend Jenna, who is pregnant with their first child. They live a seemingly perfect life in Madison, Wisconsin, surrounded by friends dealing with their own life challenges. Their relationship faces a turning point as Michael feels a growing sense of anxiety about the permanence of his choices. At a friend's wedding, he meets Kim, a charismatic college student who captivates him with her carefree attitude, leading him to question his commitment to Jenna.

As Michael grapples with his uncertainty, his friends navigate their own personal dilemmas. Izzy is heartbroken over a recent breakup, while Chris struggles in a troubled marriage, and Kenny indulges in carefree single life. Meanwhile, Jenna senses Michael's emotional distance, raising tensions between them. The ensuing turmoil forces Michael to confront his feelings and the consequences of his actions, revealing whether he can reconcile his desires with his responsibilities.