Fifteen-year-old Andrew lives in South Beach with a bunch of foxy women. Trouble is, they're all relatives. But it makes him a pseudo-expert on women and the envy of his friends.
Andrew and Keith have a new Chemistry partner meeting them called Lauren, but when she arrives she ignores the chemistry and asks Andrew on a date. After Andrew dates Lauren, he finds out that another girl, Kendall has been asking about him. He breaks up with Lauren using a stupid excuse. He then brings Kendall home, but Lauren is there, and both girls get upset with Andrew because of the way he treated Lauren. So he brings them both flowers individually and thinks he has solved the problem until they both find out that he gave the other flowers!
Andrew finds a copy of Julias will. Jordan reads it and sees that she has not been made the childrens guardian as she is not responsible enough. Jordan bets Julia that if they switch places she will prove she is responsible. So while Julia has a day of pampering, the children run riot with Jordan. When everything goes wrong, Jordan realizes that she is not ready to be a Guardian yet.
Andrew gets a date with one of Paiges friends Caroline, to Paiges annoyance. But once Paige thinks of Andrew floundering with an experienced Caroline, she decides to let him embarass himself. Andrew nervously arrives at Carolines house while her parents are away. Caroline is very flirty, but Andrew keeps pace. Instead of having sex, however, Caroline confesses that she is a Virgin. She was hoping Andrew would be too scared to carry on. Later, Paige finds out that Andrew was sensitive with Caroline and thanks him for it.
A 15-year-old Venezuelan model who is a client of Jordan's comes to stay with the family as Jordan's house is being fumigated. Andrew tries to be a good host for the model. However, his clumsy conversation and actions end up insulting her. When Andrew explains the situation, both Pilar and Julia see he was trying to be nice and apologize
Keith enlists Andrew's help in a ""foolproof"" plan to get girls interested in him. Since the school's all-star quarterback doesn't know how to use the school's e-mail system, Keith plans to write romantic messages to girls using the quarterback's screen name, Goldenarm. Keith reads the directory and selects what he thinks is a girl's name, S.B. Tigress, based on personal information in the computer user's profile. Neither Andrew nor Keith knows the true identity of S.B. Tigress. Since Keith does not understand anything about the opposite sex, Andrew writes soulful messages for his friend. After an exchange of six messages, Keith obtains a copy of the access codes for the school's intranet. The boys soon discover that the girl Andrew is writing to is really his sister Paige. Andrew arranges a meeting between Goldenarm and S.B. Tigress. But while Keith waits for Paige, Val arrives instead--wearing makeup. Val was using Paige's profile to write to the quarterback! Meanwhile, Jordan admits
Julia and the rest of the family are in charge of catering for a rich woman's Halloween party. The children are supposed to pretend they are not related to Julia though, as the woman doesn't like family businesses. When Andrew and Keith flirt with the woman's beautiful daughters, Julia 'fires' them. But the boys disguise themselves with costumes and sneak into the party anyway--causing some cases of mistaken identity.
When widow Julia finds out that Keith's divorced father Alan is romantically interested in her, she agrees to a date. Andrew is disturbed by the prospect of his mom dating again--especially because her date is Keith's dad--but she feels liberated. Alan is as weird as his son, but Julia has a good time. After the first date, however, Alan admits that he is not ready to have a new relationship. Julia informs her children that she is going to date more often.
Julia reluctantly agrees to cater for Jordan's modeling agency party. The agency boss tells Julia she would be a good model, to Jordan and Paige's disgust. Meanwhile Andrew and Keith argue over the correct way to get dates with the models and learn that their friendship is more important.
Paige anxiously awaits for a letter to say she has been accepted at Emory, a prestigious out-of-state college. When it arrives, she tells the family that she didn't get in, and will attend the local college. Julia finds out that Paige was actually accepted at Emory. Paige tells her mother that she wants to stay in town to maintain her social status with her friends. But it turns out that she feels responsible for taking care of her mom and brother and sisters and wants to live at home during college.
Andrew punches a Photographer who has upset Paige after doing a modelling shoot with her. Andrew thinks Paige is upset because Phillip forced her to pose in intimate clothing, but she is actually annoyed because the photographer (Phillip) only used her as a foot model. Julia punishes both of them and then asks her dead husband for advice. Andrew convinces Julia to let his band play at Paige's birthday party if he gets a new guitar amplifier.
Julia is having a good dinner date with a new man called Dave but then she suspects he likes Jordan. Meanwhile, Andrew must bond with a group of middle-aged fathers when he takes Elizabeth on a camping trip.
Andrew and Keith plan to create a Web site selling inside information on what women want from men. They want to sell it to Bob, a very successful businessman and good friend of Andrew's deceased father. However, after the guys get excited about the idea, Bob informs them that he will buy it after they attend business school. Later, Andrew and Keith take a standardized personality test to determine their future careers. Andrew is disappointed to learn that he is qualified to be an aroma-therapist. Andrew gets upset when Bob seems to pursue Julia romantically. After Andrew disrupts Bob and Julia's date in a coffee shop, Julia explains to him and Bob that she does not want to date anyone right now. Later, she tells Andrew that he is going to have to accept that she will date men. She also informs him, to his delight, that his test scores are identical to his father's.
Already the one who does most of the chores around the house, Andrew also endures a bossy new girlfriend, Gwen. His sisters chide him for behaving passively with a woman, but Andrew claims to be happy. Julia worries that Andrew is confused about male and female roles because she is overbearing and he has no father figure. Finally, Andrew goes to Gwen's house to assert what he wants, angering her. Andrew resents the girls getting involved and ruining his relationship. After another talk with Julia, Andrew returns to Gwen and works out a fair arrangement for both of them.
