After Penny is announced the new member of the cheerleading squad, an old friend of Dijonay's, LaCienega, shows up. Dijonay lets her try out and she "ties" with Penny. To decide between the two, Dijonay schedules a cheer-off. Behind Dijonay's back, LaCienega makes fun of Penny. She realizes that LaCienega does not just go to the same school as her, but she is also her new neighbor! Her parents invite them over for dinner to welcome them to the neighborhood. Trudy makes friends with LaCienega's mother, Sunset. Oscar makes friends with LaCienega's father, Felix. Suga Mama makes friends with LaCienega's grandfather, Papi. Penny decides not to hold a grudge against LaCienega. Meanwhile, Oscar plans a "camping trip" (to watch TV) in Felix's home theatre. The next day, Penny tells LaCienega that she is sorry and wants to be her friend. But LaCienega still doesn't want to be nice to Penny. So Penny takes Sticky to eat with the Gross Sisters. Penny tells the Gross Sisters, Dijonay chose LaCien
All Penny needs to do is clean up her room...but Oscar tells Penny to clean up the whole house. But she only gets her normal pay...five dollars. But five dollars isn't enough to see a movie with her friends. Because of this, Penny feels unappreciated...and underpaid. All of her friends feel the same way. So she and her friends decide they want grown-up money for grown-up work. To get their way, they "must" go on strike. No chores until they get a better bigger allowance pay! But because of that...they all get kicked out of their house. They'll do everything they can get get a raise of allowance. But slowly the strikers stop protesting and go back home. But Penny will not give up hope...even when there is no one left but her.
Penny is being very generous today. She is washing the dishes, making breakfast and complimenting her parents! wants to through a sleep-over on the same day as Trudy's veterinarian awards banquet. Trudy says no. Oscar thinks it's fine...but only because he doesn't want to go to the awards banquet. But Trudy drags him along. Penny suggests that Suga Moma could chaperone. Trudy thinks it's okay as long as she agrees. Penny knows she will because she and Suga Moma "speak the same language." Penny pays Suga Moma, twenty dollars to be the chaperone. her friends arrive. But before Trudy and Oscar leave, they tell them "the rules:" "No loud music, no boys, no running up the phone bill, no boys, and most importantly...no boys." Of course, what's a sleep-over without loud music and boys? Dijonay invites the boys over and starts the party music. Meanwhile, at the awards banquet, Oscar torments the pigeons by saying he eats buck. The pigeons get back at him by chasing after him. Back at the party
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.
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.
Because of a preview of a 'Wizard Kelly Spelling Bee' that Oscar saw in the 'Wizard Kelly Movie Theatre,' he thought of him being Penny's age and winning that Spelling Bee. Oscar notices that his former spelling bee rival works at the theatre. So he goes over to him to make fun of him. But his rival thinks (and knows) that Oscar doesn't even know what the words mean. For revenge, he enters his son in the spelling bee. Later, at a 'Wizard Kelly' store, Oscar goes to pick up a product to help Penny with her spelling. But there is only one left and...guess who is there! His spelling bee rival! An they are fighting over it! They broke it. Later, Oscar's spelling bee rival's son meets the Gross Sisters. And they help him cheat. But he becomes disqualified for cheating. So it's up to Penny to spell the word 'bobbin'. Can she do it? Maybe by a little help from her dad...mouthing the letters!
Penny's efforts to impress a boy at school land her on the football team; and Oscar develops a new snack food called jelly poppers.
Penny breaks her father's no-dating rule when she goes to the amusement park and pairs up with a boy named Carlos. Elsewhere, her parents go on a double date to a day spa.
Penny's grades fall victim to a longtime grudge held between her teacher Ms. Dinkins and Suga Mama; Oscar and Trudy enroll the twins in a private preschool.
Penny is entrusted with her very own credit card, which she plans on using responsibly, but it seems to have a mind of its own. Oscar, meanwhile, nearly spends his family out of house and home in his attempt to catch a mouse.
As the Proud family goes Christmas shopping, they meet a homeless family. Oscar (of course) doesn't do anything to help them. But Trudy tells Oscar to find the family and give them some money. When Penny and Oscar find them, Penny ask them if they want to have a Christmas dinner with them. They'd love to! But Oscar wouldn't. On Christmas, they arrive seven hours early and presents the Prouds with a fruit cake. Nobody thinks much of it so they give it to Bobby. He throws it out the window! When Penny gives them their presents, they don't seem to like them. Trudy, feeling a bit concerned, asks them. They say that they celebrate Kwanzaa. Oscar asks, "Kwa-whoo?" The family tells the Prouds all about it and celebrate it with them. This may be when the Prouds learn the true meaning of the holidays.
For the school dance, Penny, LaCienega and Dijonay give Zoey a makeover. At school, the next day, they think that Zoey's hogging all of the boys. But Zoey wants to be with the foreign exchange student. But when Nubia sees Zoey's makeover, she wants her older sister to have one too. After the makeover, she started hanging out with Penny. But what Nubia didn't realize is that without her older sister, she is powerless. Nubia somehow convinces her to come back to staying with her. But before she goes, Penny gives her a friendship bracelet. But will she keep the friendship?
Penny decides to throw a slammin' party, but LaCienega is throwing a party on the same night except with a guest appearance from Jennifer Lopez to blow Penny's party away. On the night of the two parties all of Penny's friends ditch her to go to LaCienega's and The Gross Sisters and Myron are Penny's only guest. Everybody tries to make Penny have a good time with the little party they have and she eventually gets even with her friends when LaCienega's party turns out to be a bust and they all go to Penny's in the end.
While grillign burgers, Oscar is finished usin a match, so he throughs it back behind him. The match lands in the bottle of kerocine. The bottle gets knocked over. And the Boulavardez's house starts on fire! Now the Boulevardez family has to move in to Penny's home. And LaCienega has to stay in Penny's room!!! Oh, the horror! The next day, their school has swiming tryouts to be on the swim team. LaCienega isn't very comfortable about it. It is because that LaCienega has really big feet. She is thrown out of the Wizard Kelly teen beauty pagent. Can Penny save her from herself and LaCienega?
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.
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.
Suga Mama needs Oscar to watch Puff. Oscar wants it to be his day off, but Trudy wants to go shopping. She demands him too, and he quickly goes. They pawn off the twins and Puff to Penny. Later, Penny is having a waterfight. When she isn't paying attention, the stroller with the twins is gone. The Gross sisters show up with a firetruck, and Penny tells them she quickly has to go because she's babysitting. The Gross sisters tell her she's whack because nobody's there. Penny runs quick to find them.
Trudy is looking for new furniture. Oscar is watching a fake T.V. football game(the cardboard.) They agree to get an expensive case. On their way home, they see kids hanging over a bridge to the river. Oscar says that they are crazy, and he wishes they were his kids so he could tell him. Trudy sees that it is Penny, and tells him. They stop, and find Penny rescuing the twins. She is about the rescue Puff, but he falls and rides down the river.
They have to go home and face Suga Mama. She is
Penny is sick and tired of the the Gross sisters. When she tries to get them to stop taking her money, the Gross sisters get really mad and want to hurt Penny. In order to hide from them, she skips school and hides at a museum. The Gross sisters find her but they don't catch her. Penny ends up getting her money back and teaches the Gross sisters about savings accounts.
There is a scavenger hunt put on by no other, Wizard Kelly. You figure out the riddles, and then go to that place and get the object. Whoever wins gets to be Wizard Kelly for a day. Also, in association with Proud snacks. Penny is walking down the street with her crew. The Gross sisters show up and jack their money as usual. When they turn around, there is a group of more bullies, and Sticky is right with them. They take the money from them, and Penny and her gang are shocked that Sticky would do this. At school, Sticky gives the money back. When Penny and Zoey complain too much though, he takes it back. The crew learns from Dijoney that Sticky's parents are divorced, and he has been weird. Penny goes home, and her parents are fighting a little. She gets a little worried and asks them if they are going to get a divorce. They explain to Penny that they love each other too much, but everyone gets in fights and she shouldn't worry. Penny tells them about Sticky stealing their money,
The hottest show around. Penny gets her girls when it comes to town. It's the hip-hop helicopter! After forming a dance group of Dijonay, Lacienaga, Zoey and herslef, the girls enter to be on the show. Dijonay's cousin offers to give them a ride, but thinks they're too lame. When they get there, they think it is amazing. Revealing skimpy outfits, the girls start dancing. Meanwhile, Suaga Mama and Oscar are head to head on bowling leauges. Oscar is an extremely poor sport. When Trudy looks up, she sees her girl on TV. Penny is in deep trouble. She promises her Mom she will never wear that kind of outfit until she moves out, even though she won.
The next day, they are very popular at school. D's cousin now thinks they are cool. She booked them to a high school party. She tells them to wear the same outfits, but Penny promised her Mom not to. She gives in because her parents will be gone. Night of the party rolls around. Penny goes. She finds the guys there only want her body. They a
Penny gets the lead part in the school production of "Romeo and Juliet". Kwok, who plays Romeo, really likes Penny and wants to run lines with her. Meanwhile, Penny's aunt Dee (a theatre actress) decides to work on the play. The drama teacher was so starstruck that he said it was okay. Trudy starts to think that her sister is trying to play the mother.
When Penny and Kwok are running lines, Oscar catches them kissing. And being as "concerned" as he is, he thinks it was an "I want to go steady with you" kiss. Penny and Kwok kissed not just for rehersing, but because they wanted to.
Later, Kwok tells Penny that he is going to get married. Penny then thinks that he was lying to her all this time. And she thought he really liked him. Penny then doesn't want to do the play. Was it all a lie? and Will Trudy put he foot down and tell her sister to back off?