Dave is a computer programmer in his mid 20s who works for a San Francisco tech company. He amuses himself in his free time pretending to be a private investigator making house calls, but he has a feeling there is more to life than duping unsuspecting housewives and stealing their maracas. Then one day, things unexpectedly fall apart. In the first 15 minutes of his workday, his girlfriend breaks up with him over instant messenger and his boss (who can’t even remember his name) lays him off. With a severance check and lots of free time in hand, Dave starts contemplating his next move. Meanwhile, his friend Brandon is ‘training’ to compete in the Pot Olympics to win a trip to Amsterdam. Brandon is in his late 20s, lives at home with his mother, and spends all day smoking pot and playing video games. His plan to win the trip is to record himself “Running the Gauntlet” - smoking a series of pipes and bongs, all in one breath. Training for this requires intense mental and physical preparation, not unlike karate masters preparing to break concrete blocks. Unfortunately for Brandon, he keeps getting interrupted by his nagging mom and Dave’s job and girl issues. When Brandon finds out Dave is unemployed, he poses the age-old dilemma faced by men in their 20s: What, exactly, is wrong with living off your parents, smoking pot, and playing video games? But Dave is more ambitious, so Brandon attempts to help his friend by suggesting things for Dave that are totally out of his skill set, like Rock Singer and Magician. Dave, open to trying new things and lacking any self-awareness, attempts them with gusto and fails miserably. While getting lunch at a sandwich shop, Dave runs into Tara, a long lost crush from college. Tara has recently broken up with her long-term boyfriend, finished grad school, and moved out to the Bay Area. Like Dave, she is unemployed and searching for a new direction. She spends her free time in bridge tournaments with her grandmother. Thinking he is seeing the hands of fate in action, Dave immediately goes after her. Undaunted by her tepid response to his overtures, he doggedly pursues her, despite warnings from Brandon about the dangers of being “The Rebound,” which he says is just as bad as being in the “Friend Zone.” Dave brushes this off, saying that what they have transcends the normal rules, because this is fate. Soon after the sandwich shop encounter, Dave panics when he realizes he has lost Tara’s phone number. Without any way of contacting her, he thinks he has lost her forever. Utterly depressed, heartbroken, and in need of a distraction, he picks a random house for his next private investigator prank, which turns out to be Tara’s. The sheer improbability of this sequence confirms in Dave’s mind that he is indeed seeing fate in action. He pursues Tara with even more fervor, and his persistence eventually pays off. After a romantic evening watching Godzilla, Dave & Tara start dating. Unfortunately for Dave, Tara just isn’t ready for another relationship (and is a little put off by his puppy-dog-like attachment to her) and breaks up with Dave, who just can’t seem to do anything right since he got laid off. Unemployed, single, depressed, he lashes out at Brandon. After a bit of soul searching and a failed private investigator prank, Dave ends up having an unexpected heart to heart with Brandon’s mom. She gives him the perspective he needs and he realizes what he should do. Since he loved being a prank investigator so much, he should become a REAL private investigator! He also realizes he was acting like a jerk to his best friend, so he takes Brandon out for a drink to make it up to him. At the bar, he meets a new girl, Michelle. Could she be the one?