Jessica James is a strong-willed woman who has recently gone through a breakup with her boyfriend, Damon. Eager to move on, she attempts to find new connections through Tinder, though she remains skeptical of the platform's success. Interestingly, Jessica has orchestrated a date primarily to provoke jealousy in Damon.
With encouragement from her best friend, Tasha, Jessica takes on a waitressing job at a glamorous Manhattan event. However, her unprofessional behavior—ranting about her troubles to anyone who listens—leaves a poor impression. From there, Tasha sets her up on a blind date with Boone, played by Lakeith Stanfield. Their meeting starts off awkwardly, with Jessica's brutally honest confession about her breakup juxtaposed against Boone's tales of his own recent divorce. Surprisingly, the chemistry clicks, and they end up spending an unexpectedly passionate night together.
Amid her endeavors, Jessica is a budding playwright, yet her efforts have not borne fruit as her works face a series of rejections. To keep herself afloat, she works with children at a theatrical workshop located in Hell's Kitchen. Boone, on the other hand, benefits from the profits of an app he developed. While Jessica has genuine feelings for him, she frequently finds her mind wandering back to her ex, Damon.
In a relatable moment, Jessica and Boone take a stroll one evening where they confess to obsessively checking their exes' social media accounts. They make a pact to unfollow their former partners, only to struggle with regrets immediately after. To cope, they prankily decide to follow each other's exes, finding a humorous way to keep tabs on the past while trying to forge ahead. That night, she experiences a bizarre dream where Damon confronts her but is suddenly crushed by a piano plummeting from the sky.
Jessica returns to her hometown in Ohio to attend her little sister's baby shower, where nostalgia strikes hard, reminding her of her lifelong love for theater and illuminating why she has felt out of place back home.
Upon her return to NYC, the pair continue dating, and Jessica’s feelings for Boone deepen. However, when she drops by his place unannounced, she stumbles upon him in a compromising situation with his ex-wife, leading to an emotionally charged misunderstanding that leaves her heartbroken.
Determined to regain focus, Jessica immerses herself in her children's workshop. During a weekend writers’ retreat, she meets her idol, Sarah Jones, who inspires her to appreciate the journey of theater over its fleeting rewards. Eventually, she and Boone meet again in a park, prompting an emotional reconciliation.
As opportunities expand, Jessica receives an exciting invitation to lead a staged reading of one of her plays in London. Boone steps up with a proposal to use his frequent-flyer miles to help her get there. Instead of having him accompany her, the story concludes with Jessica on a flight with Tasha and Shandra, one of her young students, who speculate with joy about Boone's role as her "boyfriend" in securing their free tickets for the journey.
