Daughter Angela is graduating from high school and Rev Run wants to reward her for being a straight-A student by throwing her a party. Angela dreams of a blowout complete with iPod goodie bags, a $10,000 glass dance floor over the pool, and guest DJ Funkmaster Flex. Her dad, on the other hand, has less expensive visions of hotdogs on the grill and kids dancing around the pool. Although the party didn't turn out to be Angela's vision of fly, Run's birthday gift was more than anyone expected.

Rev Run invites emerging hip-hop group, Union Turnpike, to the house to figure out how to convince his brother, Russell Simmons, to sign them to his new record label. Justine sees this as the perfect time for the girls to go to the spa. The only favor she asks of her husband is that he gives Diggy and Russy a talk about the "birds and bees." Later on, at Phat Farm headquarters, Russell gives the boys from Union Turnpike an equally awkward talk on how to make it in the rap game.

Run's blood boils upon finding that his pool house has become filled with family junk. Meanwhile, Vanessa and Angela express their desire to move out and share an apartment in Manhattan. With eyes bigger than their budget, the girls tour some of NYC's most glamorous real estate. A day of looking at penthouse apartments takes the girls from Trump's ivory tower down to the ground floor of their reality. In the end, the pool house is clean, the girls decide to stay put, and once again all is cool in Run's House.

An innocent family trip to the bowling alley turns explosive when Russy has a meltdown about losing. In an effort to teach the family about good sportsmanship, Rev Run designs a competition that backfires when the Simmons realize that Russy isn't the only one who needs to control his competitive nature.

Justine loves to eat and she and Run are struggling with the weighty consequences. Determined to slim down, Justine enlists the help of a personal trainer. Meanwhile, Angela is hungry for a shot to work at Baby Phat with her aunt, Kimora Lee Simmons. After a lot of hard work and running countless errands, Angela gets to finally walk in her aunt's shoes, if only for a moment...

Vanessa gets a modeling job in Colorado, and Dad decides that her shoot would be the perfect end of summer family vacation. The Simmons leave New Jersey and embark on their first outdoor adventure in Keystone, Colorado where "fly" is just a type of fishing.