The Prouds' and Boulevardez end up stranded when they decided to go on a camping trip together.
The twin's first birthday party goes haywire when the famous children's performer "Thingy" no shows while Oscar tries to entertain all the impatient babies.
Penny and her friends' musical group LPDZ, get a record deal but Penny is more interested in performing solo.
Penny is cast as 'Juliet' in the upcoming school play of Shakespeare's 'Romeo and Juliet.' Penny finds herself having a crush on her fellow cast member Kwok, who is playing 'Romeo,' and is nervous when she finds out there's a kissing scene in the play.
Sticky, in dealing with his parents divorce, starts hanging out with a group of bullies called 'The Altos.' In order to knock some sense into Sticky, Trudy and Penny recruit Oscar to expose Sticky to The Proud Snack Factory believing Sticky will find a positive role model in Oscar. Unbeknownst to the Prouds, Sticky has ulterior motives and steals the clues to a scavenger hunt contest being co-sponsored by Proud Snacks and Wizard Enterprises. Meanwhile, Oscar is gypped by Wizard Enterprises when his company logo is not visible to the naked eye, but when viewed under a magnifying glass, reads 'Prune' instead of 'Proud' Snacks.
Penny decides it's time to stand up to the neighborhood bullies, the sisters, who relentlessly shake down the student body for their money. When the Gross sisters hear that it was Penny who ed them out to the school principal, Penny learns how to lead them with conversation instead of confrontation in order to save her own skin. Also, Oscar and Trudy take the twins to Dr. Payne for their shots.
After the Prouds' neglect Suga Mama's poodle, Puff, he gets lost in a river and is sent on an adventure around the world. Meanwhile, Suga Mama has moved into Penny's room in order to cope with Puff's absence and the Prouds realize that it's their fault that Puff is lost. Also, Oscar and Trudy shop for an armoire.
After Penny bumps her head, she is transported to circa 1955 via a dream and experiences the true meaning of Black History month. After quickly learning that in 1955, her best friend Zoey is not her friend because she's white and integration of the school's is a new concept for the students, she uses her knowledge from the future to educate everyone on how important it is to come together as a unified people.
At a weekend b-b-q Oscar burns down the Boulevardez house; in an attempt to be a good neighbors the Proud's allow Sunset, Lacienega, Papi and Felix to move in. While sharing a room Penny knocks heads with Lacienega and Oscar feels threatened as the twins begin to refer to Felix as 'Da-Da.' This animosity subsides once Lacienega becomes an outcast in the world due to her webbed duck feet. The Prouds, in an attempt to restore Lacienega's pride help with her routine at the Wizard Kelly Teen Pageant. Lacienega brings down the crowd with her swan spectacle, which allows her to transform back to her usual self.
After her dad explicitly forbids her dating, Penny decides to sneak out to an amusement park for a 'group date' with her friends-only when the girls pair up with the boys, Penny is stuck with the rather rotund Carlos. While initially disgruntled, Penny discovers that Carlos is a sweet, funny, and confident kid and ends up having the best time of all her friends. Once back home her date is revealed, but Oscar is relieved to discover that Penny learned a valuable lesson about getting to know a person on the inside. Also, Trudy and Sunset drag Oscar and Felix on a 'date' to a day spa.
Penny's obsession with a cool, new boy-Mega-turns into an obsession with the 'napster-like' website he created. Knowledge of the website spreads like wildfire and soon kids all over the world are downloading free music and depriving the record companies of their income. When the economic downturn hits Proud Snacks, Penny realizes she shouldn't have let Mega's coolness blind her to what is right and wrong.
It's 'take your daughters to work day' and Penny decides that a day spent with any other mom would be far more interesting than a day with her own. Determined to reconnect with her daughter, Trudy drags Penny to her veterinarian clinic where she ends up curing an ailing circus tiger whose thoughts she can somehow hear. When the tiger escapes the circus in a desperate attempt to go home, Penny turns to the one person on whom she knows she can depend, her mom, to help send the tiger back to India. Meanwhile, Oscar, his brother Bobby, and Felix peddle ice cream at the Wizard Kelly All-star game.
When Penny discovers that she and her friends don't have even enough money for the Gross sisters to steal, she decides to organize a neighborhood strike for more allowance. With chores left undone, the standoff begins, and the kids decide to form their own 'teen-city' where they'll build their own shelters and live off the land. When morale quickly erodes, Penny soon finds herself out on strike alone. A conciliatory visit from Oscar makes Penny realize that allowance isn't a right but a privilege, and she also learns she's a lot like her dad-stubborn.
Penny's got the last spot on the cheerleading squad locked up-that is until Dijonay's preschool friend, Lacienega, shows up, and show's her up. To make matters worse Lacienega and the rest of the Boulevardez family have moved in across the street. When Penny has enough of Lacienega's vicious taunting, she mistakenly enlists the Gross sisters' help and must then save Lacienega from their wicked plan. Meanwhile, Oscar becomes obsessed with Mr. Boulevardez' amazing home theater.
The entire gang is impacted when a Valentine's Day crush on Penny results in graffiti around school. After discovering the culprit is Johnny, Penny chooses to be nice and invite Johnny over Johnny's lack of respect for the Proud Family puts him on everyone's bad side and Penny resorts to being upfront with Johnny. For Valentine's Day Trudy gives Oscar a Chef O'Boy dinner and Oscar reciprocates with a little ski vacation. Penny brings Johnny along and Oscar's good intentions backfire on him.