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.

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.