Bob doesn't like the girls Phil has been bringing home lately so he decides to find Phil a nice girl. His search includes a singles mixer and putting an ad on a billboard.

Phil, Bob and friends head to NYC where Phil hopes to get the cover of Transworld Wake Magazine during a photo shoot in front of the Statue of Liberty. Bob sets out on the streets of New York in search of local superhero.

Phil's latest business investment, a country bar in downtown Orlando, is about to have its grand opening. Feeling like he needs to expand his career, Bob makes a business proposal to help Phil promote the bar.

Bob has always wanted to own pet llamas and decides to make his dream come true. Phil is not thrilled with the new house guests and kicks them out leaving Bob and the llamas to fend for themselves.

Phil and Bob's younger brother Jason is training for one of the first wakeboarding events of the season. He looks to his older brothers for extra guidance but their methods both on and off the water couldn't be more different.

After hearing about the Asian Carp infestation near the great lakes, Bob decides to take the gang to Illinois to wakeboard on the river through the jumping Carps. During the trip Bob hooks up with Alexa, a long time friends.

After getting closer on the trip to Illinois, Bob wonders about the status of his relationship with Alexa. Can he work up the nerve to ask if she's his girlfriend? Will she say yes? And what will Phil think?

Phil & Bob's Grandma Sondra drives up from Miami to visit for the weekend. While Grandma's in town, the guys accommodate her active lifestyle and Bob tries to get Granny and Phil to approve of Alexa.

Phil travels for a tour stop and Bob is forced to undergo surgery for a recent injury. While Phil works to maintain his number one standings, Bob partakes in some strange healing methods.

The guys travel to Ft. Worth, TX for a King of Wake tour stop. Even though Bob can't compete, he's determined to get attention for his crazy antics, including throwing Phil a birthday party he'll never forget.