Astor, Fran Kranz, a zoology major, has cherished a childhood dream of being with Mila, Beau Garrett, for as long as he can remember. On his birthday, after a night of drunken revelry, he brings her home to care for her while she’s sick, and what begins as a playful, awkward courtship quickly stalls, leaving Astor with a bruised ego and a romance that ends almost as soon as it starts.
Still obsessed with Mila, he turns to her close friend Cali, Dichen Lachman, who has recently fallen out with Mila for reasons nobody fully explains. Cali agrees to mentor Astor in the art of picking up women, teaching him to be confident and authentic rather than performative. She argues that true love involves sex and connection, not abstinence, and she recalls Mila’s volatile past: Mila used to smoke, and when they were kids, an incident nearly exposed Mila’s limits—she even recalls a moment where Mila pressed out a cigarette on Astor’s chest. Through Cali’s coaching, we flash back to Astor’s earlier sensitivity: he was a caring, attentive lover who wrote heartfelt poems about Mila and spoke of their time together in lyrical terms. He even joined a cardiology course to help Mila study, taking exams for her and scoring an 89, while his own zoology grades slipped.
Astor’s devotion to Mila runs deep and romantic. He is almost comically earnest in his expressions of love, and Mila’s social circle includes a bold, flirtatious crowd. Jake, Mila’s popular friend, repeatedly tries to humiliate Astor in public, a dynamic that Mila tolerates but Jake enjoys. Mila’s friend Jenny, played by Miracle Laurie, appreciates the sincerity of Astor’s feelings for Mila. One day, overhearing Mila tell Jenny that she wants a “manly man” who can unhook a bra, Astor realizes how far his approach must bend, pushing him deeper into Cali’s training. During this period, a Catholic girl named Susie enters the scene, embodying a strict “no sex before marriage” stance that contrasts with Astor’s evolving self-image. Cali also introduces a dramatic subplot with Franck, a Frenchman [Karim Saleh], whose tumultuous fling with Cali ends when she discovers his cheating.
Despite Cali’s guidance, Astor continues to misfire at parties; his charm remains awkward and his lines fall flat, yet Cali stays by his side, defending him in front of women who call him pathetic. He accompanies Cali to various social settings and even tries to win Mila over by returning her underwear—a moment that underscores his longing and his stubborn cling to romance. A confrontation with Jake in a bar escalates into a crude display, but it ultimately passes without a lasting resolution.
A neighbor named Divinity enters the picture, and Astor finds Divinity irresistibly attractive, though Divinity sometimes acts as if she barely notices him. Under Cali’s influence, he navigates a tense interaction with Divinity that nearly leads to sex, but a phone full of Cali’s goading texts reveals her manipulation and finally makes Astor realize Cali cares for him more deeply than any other woman he has known. Divinity’s charms complicate matters further, and in a moment of bold risk, Divinity invites him into an intimate moment that could have changed everything.
Then a revelation hits: Divinity and Trinity are twin sisters. The twist reframes every interaction, and a heated threesome with the twins unfolds as Mila unexpectedly arrives on the scene. Mila, who has returned to see how things have changed, tells Astor that she appreciates what he did for Jake and that she’s breaking up with him, while also discovering that Trinity and Divinity exist and that Astor has moved on. Mila offers him a second chance at a relationship, warning that sleeping with the twins would end their friendship, which forces Astor to assess what he truly wants. In the wake of this, he realizes he doesn’t love Mila in the way she imagines, and he ends things with her. Mila hints that Cali loves Astor, prompting a period of quiet reflection that lasts several weeks.
After three weeks of contemplation, Astor recognizes the truth behind Mila’s hint and the deep bond he shares with Cali. He gathers his courage and proposes to Cali, who accepts, signaling a shift from elusive romantic fantasy to a future built on genuine connection and mutual devotion. The journey through longing, misdirection, and self-discovery culminates in a promise of commitment, with Cali embracing the role of partner and confidant in Astor’s life.
