Risky Business (1983) Timeline Explained – Every Event in Order

Joel's Aspirations

High-achieving student Joel Goodsen’s life is largely influenced by his wealthy parents, particularly his father, who is a Princeton alumnus. With hopes for Joel to follow in his footsteps, his father encourages him to participate in the Future Enterprisers program designed to foster entrepreneurial skills in high school students.

Where

Glencoe, Chicago

A Night of Freedom

With his parents out of town, Joel's adventurous friend Miles convinces him to take advantage of his temporary freedom. That first night, Joel indulges wildly, raiding the liquor cabinet, blasting music, and joyriding in his father’s car while dancing in his undergarments, fully embracing a carefree lifestyle.

Where

Joel's home

A Surprising Encounter

The following day, Miles arranges a date with a prostitute named Jackie for Joel. However, Jackie's true identity as a male cross-dresser surprises Joel, prompting him to quickly end the encounter, although Jackie manages to connect him with another escort, Lana.

Night with Lana

After nervously calling Lana, Joel is instantly captivated by her beauty and spends a night of passion with her. The exhilaration of their connection promises a thrilling escape from his otherwise structured life.

Where

Joel's home

Unexpected Fees

The next day, Lana requests $300 for her services, unexpectedly throwing Joel into a dilemma. He rushes to the bank but returns to find her gone, along with his mother’s prized Steuben glass egg, prompting a frantic search for both.

Where

Joel's home

Facing Guido

In his quest to retrieve the stolen egg, Joel confronts Lana's imposing pimp, Guido. The encounter escalates into a life-threatening situation when Guido threatens Joel with a gun, leading to a thrilling chase in his father’s Porsche.

Lana Stays Over

After revealing that her valuable belongings are at Guido’s lair, Joel agrees to let Lana stay at his house. This decision leads to unforeseen complications as his friends gather for an unexpected visit, setting the stage for chaotic interactions.

Where

Joel's home

Marijuana Mishap

The atmosphere shifts to a more relaxed vibe as Joel, Lana, Vicki, and Barry share marijuana together. However, things go awry when Lana accidentally nudges the Porsche out of gear, sending it crashing into Lake Michigan, resulting in the car's unfortunate demise.

Where

Lake Michigan

Desperate Solutions

Facing exorbitant repair costs for the sunk Porsche, Joel and Lana concoct a plan to transform his home into a temporary brothel for one night. The party attracts a crowd of Joel’s classmates and Lana's friends, generating unexpected income.

Where

Joel's home

Rutherford's Visit

Coincidentally, the wild party coincides with an important interview from Princeton recruiter Rutherford, who assesses Joel for admission. Despite the distractions, Rutherford becomes acquainted with the chaos surrounding Lana and her colleagues, potentially influencing his impression of Joel.

Where

Joel's home

An Intimate Moment

As the party winds down, Joel and Lana find a moment of intimacy on the Chicago 'L', deepening their connection amidst the chaos. This night marks a significant shift in their relationship, leaving them both reflective on their experiences together.

Where

Chicago 'L'

Burglary Shock

When Joel returns home after retrieving his repaired car, he is shocked to discover that a burglary has taken place. Further complications arise when he learns from Guido that he can buy back his stolen furniture.

Where

Joel's home

Last-Minute Preparations

In a frantic race against time, Joel and his friends work to restore the house before his parents return from their trip. They manage to clean up just as his parents arrive, though Joel's mother notices a crack in her beloved egg, hinting at the chaotic events that transpired.

Where

Joel's home

Father’s Praise

Despite the chaos of the last few days, Joel's father praises him for impressing the Princeton recruiter during the tumultuous night. This validation secures Joel's acceptance into the prestigious university, marking a bittersweet resolution to his tumultuous adventures.

Uncertain Future

In a reflective moment at a restaurant, Joel shares a quiet conversation with Lana, contemplating the potential of their relationship. He jokes about the cost of continuing to see her, which leaves an air of uncertainty about their future together.