The guys attempt to sneak into the Playboy Mansion as uninvited guests. Meanwhile, they help a group of underprivileged kids by providing their classroom with a new computer.
The boys try to make a toast at a local wedding. Meanwhile, they help an artist get in touch with a son he hasn't seen in 17 years.
The boys try to crash the Transformers 2 red carpet and get Ben a date with Megan Fox. Meanwhile, they help a young girl get over her fear of rollercoasters.
The boys try to find a woman that will allow them to help deliver her baby. Meanwhile, they help a young woman travel to Denver to see her mom's gravesite for the first time.
The boys try to learn how to krump and enter a contest. Meanwhile, they try to help a young man get one of his songs on the radio.
The boys try to get a game of basketball going with the President of the United States, Barack Obama. Meanwhile, they try to help get a group of old friends together to bring back old memories.
The boys try to sneak onto a late night television show to tell a joke. Meanwhile, they try to help a man who went blind from a motorcycle accident re-live his favorite childhood pastime.
The boys find themselves in a small town and try to throw the most badass party with a guest appearance by Naughty by Nature. Meanwhile, they try to reunite an adopted man with his birth father.
The guys attempt to streak the Kansas City Wizards soccer game. Meanwhile, Jonnie and Dave head to Douglas, where they help build a skate park memorial in honor of the four teens who died there within a year.
The boys, excluding Jonnie, land in Nashville to redeem the failure from Season 1, asking out the girl of their dreams which Duncan has his mind set on asking out Taylor Swift at the Country Music Awards. Meanwhile, Jonnie heads back to his hometown in British Columbia, to help an older gentleman find his soul mate that he lost contact with years ago.
Duncan tells the story of when Taylor Swift responded to him. Duncan asked Taylor on a date in episode two of season two ("Ask the girl of your dreams on a date"). She sent him a text later saying "Yes"
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.
Daves Wife tells the story of his proposal.
(Bonus Story) Johnnie visits his hometown of Victoria, Canada. He gives a quick tour of his favorite spots and helps out the family of Joyce Hook.