New York City Serenade

Owen, an aspiring filmmaker, learns that his short film has earned an award nomination. His friend Ray appears in the film, and this recognition highlights Owen's ambitions within the industry. The nomination sets the stage for the evening’s events and the pressures around Owen's career.

Owen is engaged to Lynn, signaling a stable personal relationship amid his busy career. The engagement anchors his personal life as he navigates professional pressures and his friends’ problems. This commitment will be tested by the coming misadventures.

Owen and Lynn go to a film together, hoping for a quiet date night. They meet Lynn’s French literature professor Noam at the cinema, introducing a potential complication in Owen's relationship. They also catch the end of Ray’s band performance during the night.

After the date, Ray persuades Owen to help move his band's drums, drawing him into another favor. They end up heading to Bertrand's party as part of the plan, intertwining Owen’s personal life with Ray’s circle. The favor begins a chain of increasingly reckless decisions.

At Bertrand's party, the mood shifts and Owen ends up in bed with Rachel. The encounter deepens the entanglements between Owen and people in Ray’s circle. This moment foreshadows the consequences that will ripple through Owen's relationships.

Owen, Ray, and two friends are asked to serve as pallbearers for their friend Matt's father in New Jersey. The trip requires them to travel, separating Owen from Lynn for a period. The somber event contrasts with their usual nightlife and adds strain to their relationships.

While Owen is out of town, Lynn and Rachel meet, and Lynn discovers the truth about what Owen and Rachel did. The revelation shatters Lynn’s trust and prompts her to consider ending the engagement. The tension marks a turning point in the couple’s dynamic.

Owen takes Ray to the film festival, hoping the trip will yield him an award. Their driver, Les, is supposed to take them to the airport motel, but a chance sighting leads to a different plan. The festival trip becomes a test of Owen’s ambitions against his messy personal life.

Ray learns that Wallace Shawn is staying at the Four Seasons and fabricates being Shawn’s son to gain access to a nicer room. He and Owen end up in a luxury suite, a symbol of their escalating deception. This deception will soon unravel and threaten Owen’s career.

At the festival, Owen does not win any award. After returning to the hotel, their scheme is discovered and they are kicked out. The failure emphasizes the consequences of their reckless choices on both personal and professional levels.

Back home, Owen repeatedly calls Lynn in an effort to make up, but she never answers. The unanswered calls symbolize the irreparable strain placed on their engagement. The film implies they will not reunite.

In the aftermath, Lynn is shown preparing for a date with Noam, indicating that she has moved on from Owen. The dynamic shift emphasizes the personal costs of Owen’s decisions. Noam becomes a new constant in Lynn’s life.

Some time passes and Ray has straightened his life out, maintaining a good job and a solid relationship with his daughter. He has found stability despite a troubled past, illustrating personal growth.

Owen goes on to produce a successful television commercial, signaling professional progress and a pivot from the earlier chaotic events toward a new milestone in his career.