Doug has recently relocated to Portland, where he now lives with his sister, Gail. Having previously studied forensic science in Chicago, he decided to abandon his academic pursuits. One evening, they share a meal with their mother and stepfather before Doug convinces Gail to accompany him to the coast for a spontaneous day out. To make ends meet, Doug secures a job at an ice factory, where he makes a good friend in his co-worker, Carlos.
As fate would have it, Doug’s ex-girlfriend, Rachel, arrives in Portland to train at her workplace. Inviting them both over, Doug, Carlos, and Rachel, along with Gail, indulge in games together, strengthening their bond. Carlos, who is also a DJ, invites the trio to one of his sets, where they dance the night away. Doug also introduces Carlos to the intriguing world of Sherlock Holmes novels, while Carlos and Rachel find themselves attending a Star Trek convention together, adding to their growing friendship.
However, the mood shifts one night when Carlos visits Doug in distress, revealing that Rachel failed to show up at his DJ gig and is now missing. Concerned for her safety, Doug reluctantly agrees to accompany Carlos to Rachel's motel. Upon arrival, they notice a man lurking in the parking lot, who quickly drives away when confronted. After another visit to Gail, Doug and Carlos return, decoding a message involving baseball statistics that points to a man in a cowboy hat.
With the help of Gail’s research, they uncover a meeting time and place, and to their relief, Rachel appears. She explains her predicament involving Jim Warden, the mysterious cowboy hat-wearing photographer who had asked her to deliver a briefcase full of cash but instead stole it from her. Determined to help her, Doug vows to retrieve the stolen briefcase.
Using clues from Jim's photographs, Doug is able to find his house, and he and Carlos wait for the right moment to follow him. As Jim exits his home, Doug and Gail become the determined duo that shadows his every move. They track Jim to a restaurant where he is set to meet someone, and here, they concoct a daring plan to steal back the briefcase. Gail cleverly disguises herself while Doug removes their car's license plate to avoid detection, and they spring into action.
Gail securely grabs the briefcase and makes a swift escape to the car where Doug is waiting in the passenger seat. Despite Jim's frantic pursuit, they manage to evade him, driving onto the desolate rooftop of a nearby parking garage to regroup. Doug calls Carlos and Rachel to let them know they've gotten the briefcase back, and together, Doug and Gail unwind, listening to music in their car, content in their small victory.
