Baby It’s You

In Trenton, New Jersey in 1966, Jill Rosen, a promising high school actress from an upper-middle-class Jewish family, meets Sheik, an Italian boy who dreams of following Frank Sinatra's path. They begin a relationship despite their different backgrounds and expectations. Jill is on track for Sarah Lawrence, while Sheik nursed ambitions of stardom.

Jill, a successful high school actress, rebuffs Sheik's romantic and sexual advances, setting clear boundaries. The tension between their ambitions and backgrounds fuels their turbulent romance.

Sheik has a one-night stand with Jody, Jill's sexually active friend, which unsettles the circle. Jody then makes a half-hearted suicide attempt, underscoring the volatile dynamics surrounding the couple.

Following the tumult, Sheik is expelled from school, marking a rupture that pushes him toward uncertain prospects. This upheaval foreshadows his impulsive choices.

After an attempted robbery and a police pursuit, Sheik steals a car and drives to Miami, Florida, leaving his hometown behind in search of opportunity and a new start. The trip signals a drastic turn away from his earlier life.

Fall 1967 marks her departure for Sarah Lawrence College in Yonkers, New York, beginning a new chapter away from Sheik. There she befriends Leslie, who introduces her to Steve, and the two couples begin to double date. The new social circle contrasts with the old romance.

Jill settles into college life and begins double dating with Leslie and Steve, balancing old romance with new friendships. The nostalgia for her high school romance with Sheik lingers alongside her college life.

During spring break, Jill visits Sheik in Miami and sees how little he has achieved: he washes dishes at a Miami Beach nightclub and lip-syncs Sinatra on weekends. The contrast between his faded ambitions and Jill's growing opportunities is stark. This visit underscores the distance between their lives.

Jill has sex with Sheik during the visit; the moment of intimacy includes a conversation when he explains the origin of his nickname, traced to the Sheik brand of condoms. The revelation hints at a fragile self-image built around Sinatra-era pop culture.

Some time after Jill's return to Sarah Lawrence, she sleeps with Steve, moving past first romance and into a more ambiguous emotional terrain. The encounter marks a shift from the Sheik affair toward a more complicated love life. Sheik's absence continues to loom.

When Sheik arrives at Sarah Lawrence and finds Jill not there, he trashes her room and waits for her return. He declares his love, but Jill tells him she does not love him, and has no desire for the life he will have.

In a moment of dignity amid heartbreak, Jill asks Sheik to take her to a college dance, seeking one last shared experience. The moment underscores the unresolved tension between them and the limits of their romance.

At the college dance, the era's cultural shift is felt as they request the band to perform Sinatra's Strangers in the Night, a song tied to their high school courtship. As the song plays, they share a slow dance and look into each other's eyes, acknowledging their divergent paths.