Gun Shy

Gun Shy

Year: 2000

Runtime: 101 min

Language: German

Director: Eric Blakeney

Budget: $14M

ComedyRomanceCrime

A reserved bachelor's solitary existence takes an unexpected turn when a vivacious and unconventional woman enters his life. They find themselves entangled in a series of quirky events, investigating family mysteries and pursuing forbidden romances. As they work together, an unlikely friendship develops, leading to unforeseen romantic possibilities and a deeper understanding of themselves and each other.

Warning: spoilers below!

Haven’t seen Gun Shy yet? This summary contains major spoilers. Bookmark the page, watch the movie, and come back for the full breakdown. If you're ready, scroll on and relive the story!

Timeline – Gun Shy (2000)

Trace every key event in Gun Shy (2000) with our detailed, chronological timeline. Perfect for unpacking nonlinear stories, spotting hidden connections, and understanding how each scene builds toward the film’s climax. Whether you're revisiting or decoding for the first time, this timeline gives you the full picture.

1

Bust goes wrong and Charlie pays the price

Charlie's undercover operation spirals out of control when the bust goes wrong. His partner is killed, and he ends up with a gun shoved in his face just as backup finally arrives. The trauma triggers enduring anxiety and gastrointestinal problems that haunt him afterward.

During the bust
2

Post-bust life and mounting anxiety

He's haunted by the aftermath of the bust, struggling with anxiety and GI issues that complicate his work. Once known for his ease on the job, he now doubts his ability to return to the field. The dream of retirement begins to feel like a lifeline.

After the bust
3

Requests to retire denied by bosses

Desperate to step back, Charlie asks to be taken off the case or allowed to retire. His bosses, Lonny Burke and Dexter Helvenshaw, deny the request, citing the time and cover they've invested in him. The pressure to stay in the operation escalates.

4

Dream of Ocean Views retirement

He fantasizes about retiring to Ocean Views, a luxury housing complex with servants and amenities. The dream gives him a future to cling to when the present becomes unbearable. It becomes a motivational undercurrent for his choices.

5

Flight to New York and new contact

On the flight to New York City, a chance conversation with a fellow passenger foreshadows his connection to Dr. Bleckner. The encounter plants the seed for seeking psychiatric help. The trip to NYC marks the move from withdrawal to help-seeking.

During the flight to NYC Flight to New York City
6

Dr. Bleckner prescribes anti-anxiety meds

In New York City, Dr. Jeff Bleckner listens to Charlie's troubles and prescribes anti-anxiety medications. Bleckner also encourages him to join a group therapy session to address his stress. This marks the formal start of Charlie’s treatment outside the field.

New York City
7

Group therapy session introduction

Charlie attends a group therapy session and befriends a circle of stressed-out men from the business world. The sessions reveal shared anxieties that mirror his own, creating a fragile sense of camaraderie. He starts to open up about the pressures of his undercover life.

Group therapy session
8

GI doctor visit and Judy Tipp

Seeking relief for his GI issues, Charlie visits a doctor and meets Judy Tipp, the free-spirited 'Enema Queen'. Judy introduces him to alternative therapies and also becomes a romantic interest. Her unconventional approach offers a new path for his health and mood.

Doctor's office
9

Return to duty and high-stakes negotiations

Back on duty, Charlie enters negotiations for high-stakes money laundering and stock manipulation. The deal group includes Fidel Vaillar and his bodyguard Estuvio Clavo. The operation puts him in close contact with powerful and dangerous players.

New York
10

Fidel Vaillar and Estuvio Clavo join the circle

Fidel Vaillar is introduced as the son of a prominent Colombian drug lord who fears being pigeonholed as a stereotype. He relies on Charlie to negotiate and navigate the criminal landscape, while asserting his own brand of leadership. Estuvio Clavo serves as his loyal guard and ally.

New York
11

Fulvio Nesstra enters as mob antagonist

Fulvio Nesstra enters as the Italian mob’s volatile representative in New York. His temperament is unpredictable and he fosters tension within the group. He embodies the volatile nature of organized crime deals in the story.

12

Fulvio Nesstra's lineage complicates loyalties

Fulvio is the disfavored son-in-law of Carmine Minetti, a high-ranking mobster, which adds personal stakes to the negotiations. His status creates friction with rival factions and within the group's dynamic. The backstory heightens the sense that loyalties are shifting.

13

Jason Cane joins the group

Jason Cane, a young Wall Street-type with a plan but questionable taste, completes the negotiating group. He brings technical savvy and financial ambition to the operation. His presence underscores the intersection of corporate finance and criminal activity.

14

Hidden motives beneath the surface

Though the players think they understand one another, there are deeper motives and hidden loyalties beneath the surface. The ensemble's dynamics reveal that appearances mask more complex agendas. The timeline hints at betrayals, shifting alliances, and secrets yet to unfold.

Last Updated: November 22, 2025 at 15:58

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Gun Shy Summary

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Characters, Settings & Themes in Gun Shy

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