Aspiring journalist Blake Conway (Jessica Barden) writes a column titled "The Hopeless Romantic" for her school newspaper, but her editor River Dewan (Avan Jogia) abruptly cancels it, criticizing its lack of excitement. However, River proposes that Blake can revive the column if she can come up with more engaging content. In a twist of fate, during a night out, Blake's roommate and best friend Nikki Morrison (Hayley Law) accidentally swaps their IDs. The next morning, Blake unknowingly possesses another student’s identification, leading her to an unexpected meeting with Morgan Cruise (Camila Mendes), who is accompanied by an older gentleman.
During this encounter, Morgan reveals her identity as a sugar baby, and her suitor offers Blake a significant sum to stay the night – a proposition she politely declines. The following day in an editorial meeting, Blake discovers that another journalist, Jacob (Brett Dier), is competing for a prestigious Gonzo journalism award with River's support. Feeling envious, Blake resolves to secure her own column and decides to interview Morgan about her experiences as a sugar baby. This leads her to a lively pool party where she meets Ian Brooks (Timm Sharp), a wealthy professor who tries to recruit her as his sugar baby, but Blake turns down the offer.
As she writes an article about her encounter with Morgan, Blake's confidence grows, but River’s enthusiasm diminishes when he starts to perceive her piece as a thinly veiled attempt to exploit her own journalism. Undeterred, Blake and Nikki attend a themed party, where Blake comes as Raoul Duke, only to find Jacob in the same costume. Following their night of drinks, Jacob's horror surfaces when they realize he is unprepared for intimacy, lacking protection.
With her ambition driving her, Blake begins to pursue romantic interests with Ian, hoping to outshine Jacob in the journalism race. Their first date leads to intimate encounters, but initially, Blake feels unfulfilled. However, when Ian unexpectedly surprises her with a scooter, her column takes off, capturing significant attention. When Jacob questions the ethics behind her writing about Ian, Blake defends her decision, arguing for the anonymity of her columns. This growing spotlight further energizes her ambitions, and she asks Ian for a recommendation letter for the journalism award, which he agrees to provide.
One night, after an unanticipated experience involving a laced cupcake provided by Nikki, Blake becomes enchanted by Ian’s extravagant gift of a diamond bracelet, and she naively agrees to attend a wedding with him. Unbeknownst to her, this wedding belongs to Morgan’s sugar daddy, intensifying the surreal nature of the event. After a series of problematic interactions, Blake escapes without informing Ian, plunging her into a reflective crisis about the nature of her relationship with him - questioning whether it borders on transactional.
As their dinner approaches, Blake tries to deepen her connection with Ian, but his vague responses heighten her apprehensions. Despite her worries, they give in to their passions, leaving Blake feeling unfulfilled. After a night of contemplation under the stars, she discovers Ian's surprise return of her stolen bike, which had a significant meaning to her. As she makes her way home, draped in a bed sheet, she stumbles upon Jacob, who, recognizing her heartache, invites her to breakfast. Their shared understanding as children of divorce creates an immediate bond.
However, this bond is soon put to the test when Ian confronts Blake, having pieced together her candid writings about their intricate relationship. His ominous threats about jeopardizing her career and withdrawing his support for the award leave Blake in turmoil. With the pressure mounting from her choices, Blake decides to sell the diamond bracelet that Ian gave her, choosing to publish her column under her real name rather than retract it. This act of defiance showcases her unwavering commitment to honesty.
As graduation looms ahead, a mysterious message from Jacob urges Blake to meet him at the bleachers. There, he tenderly reenacts the iconic ending from Sleepless in Seattle, highlighting Blake’s love for the film. In a moment filled with tenderness, they share a kiss, making it apparent that their paths are becoming intertwined, marking the start of something new.
