Jimmy Shive-Overly, a self-absorbed British author, and Gretchen Cutler, a cynical music publicist, meet at a mutual friend's disastrous wedding. Despite their mutual disdain for conventional romance, an intense night of casual sex sparks a chaotic, volatile connection. Both are deeply commitment-phobic disaster areas, yet they inexplicably find themselves drawn back together. As they navigate early dating, their mutual neuroses collide, but they reluctantly realize they cannot live without each other, transitioning from hesitant partners to cohabitating reluctant lovers.As the relationship deepens, underlying psychological struggles threaten to implode their fragile dynamic. Gretchen is secretly battling severe, debilitating clinical depression, a reality she hides beneath a veneer of apathy and hedonism. When Jimmy discovers her secret, his initial panic gives way to a clumsy, devoted effort to support her. Meanwhile, Jimmy struggles with abandonment issues stemming from his
eccentric family and the sudden reappearance of his estranged ex-fiancée, Becca, who is now married to his dull frenemy, Vernon. Alongside Jimmy’s slacker roommate Edgar, a war veteran battling PTSD, and Gretchen’s sweet, overly earnest best friend Lindsay—whose own marriage to Paul crumbles—the core foursome forms a dysfunctional
surrogate family.Following a romantic camping trip where Jimmy impulsively proposes, Gretchen experiences an internal crisis, feeling unworthy of love and trapped by domesticity. On their wedding day, overwhelmed by the pressure of lifelong commitment, Gretchen has a panic attack and flees the venue. Instead of breaking up, Jimmy proves his unwavering loyalty by chasing after her and offering a radical compromise: they will forgo the wedding and simply choose to be together every single day without the legal construct of marriage.Their resilience is tested further during a brutal, multi-year time jump that explores their future. Jimmy and Gretchen experience a prolonged period of domestic stagnation, career frustration, and growing resentment. Jimmy temporarily abandons Gretchen after a massive argument, bringing them to the precipice of a permanent breakup. However, facing the terrifying prospect of a life without one another, they reconcile. The series ultimately concludes with Jimmy and Gretchen finally getting married years later, not out of societal obligation, but as a deliberate, hard-won choice. Surrounded by their deeply flawed friends, they embrace their unconventional, messy love story, proving that two deeply broken people can find lasting happiness by simply being the worst together.