Tom McHugh is a shy and introverted young man who longs to ask out his beautiful neighbor, Geena Matthews. When Tom's charismatic older brother, Craig, unexpectedly shows up in town, Tom sees an opportunity to impress Geena and seeks Craig's help. Craig, ever the smooth talker, outfits Tom with a stylish makeover, fancy clothes, and even lends him his car. With a newfound confidence, Tom finally asks Geena out on a date, which she surprisingly accepts. However, what starts as a promising evening quickly spirals into chaos when Tom realizes that Craig has unwittingly dragged him into a dangerous web of mistaken identities and criminal elements.

Throughout the night, Tom faces a series of increasingly bizarre and perilous situations that test his courage and resourcefulness. From evading shady figures who mistake him for his brother to dealing with unexpected law enforcement encounters, Tom must navigate one challenge after another. As Tom and Geena race through the city trying to piece together the puzzle of Craig's mysterious life, they form an unexpected bond that transcends the madness surrounding them. However, the true nature of Craig's involvement and the ultimate resolution of their misadventures remain uncertain as the night progresses.