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When the moment for Jonnie to streak the Kansas City Wizards soccer game arrives, the plan for the other three boys to help him get away by posing as stadium employees goes awry. But a night in the slammer doesn't stop Jonnie and Dave from heading to the small town of Douglas to build a skate park memorial in honor of the four teens who died there within a year.

Following Ben's failure to ask out Meghan Fox in Season 1, the boys tackle this list item once again. This time around, Duncan seeks out his dream girl, Taylor Swift. (The two met briefly at an airport, and Duncan was taken by her immediately.) Duncan, Ben, and Dave plot to crash the CMT Awards in Nashville, Tennesse, where they know they'll find the country crooning cutie.

The boys head to Vegas to help Dave find a bride within 72 hours and plan the most epic bachelor party to send him off into married life. But the craziness of Vegas doesn't stop Jonnie and Duncan from taking time to help Rick, a once successful but now homeless 47-year-old, who hasn't seen his daughter in 11 years, and has never met his granddaughter.

After rigorous training with Zeke, a professional bounty hunter, the boys are sent into the field to follow an assignment of their own: A 250-pound, 6'2" criminal known for his violent tendencies. In the midst of scouting locations, Ben and Duncan help an underrated band whose music they love get in front of a major record executive.

After exhausting a lot of dead-end leads, the boys befriend the paparazzi for tips on where they can find Robert Pattinson -- and steal a lock of his hair. Later on, they find themselves face-to-face with the A-lister at an exclusive Hollywood club. Meanwhile, Ben heads to Minnesota to meet Lexi, a young woman whose goal is to create a forum for people to discuss the pitfalls of depression -- something she and Ben have both suffered from.

There is no civilization on the islands of Aitutaki in the South Pacific. Once dropped there, the boys have to make their way to civilization without any possessions other than the sole item each is authorized to bring. They will face several serious challenges, including feeding themselves, maintaining their sanity, and avoiding natural dangers along the way.

Can novice Dave survive in the ring against a professional Mixed Marshall Arts (MMA) fighter? Ben and Jonnie help Dave train for the big event while Duncan goes on a motorcycle journey to help Sara get closure in the wake of her dad's sudden death.

Duncan, Ben, and Dave head to Iowa to crash the state parade and perform a song and dance routine a la Ferris Bueller, while Jonnie is in Canada helping Zoe orchestrate a protest to stop a major corporation from destroying Avatar Forest.

With $100,000 in seed money, the boys aim to make a million bucks. They split the original pot into four chunks of $25,000, and each go about their own secret, money-making missions. Dave befriends billionaire Tonny Sorenson (Von Dutch clothing) who helps him promote his own clothing article at a trade show in Vegas for sales commissions. Duncan heads to Wall Street to apprentice with Jim Cramer before investing his sum. Jonnie goes to Silicon Valley. And Ben heads to the race track.

After their individual money-making schemes prove to be a bust, the guys head to Vegas and, with the help of a psychic and Taylor Swift, try to win a million dollars at the roulette wheel. Later on, they head to Florida with their winnings/donations to surprise a fan who wants to make a difference in her native country.