Previously on Party of Five: Claudia freaks out when she thinks her Yalie tour guide is stalking her, and then wonders what's wrong with her when she realizes he's not. Gus agrees to let Charlie try making his furniture designs (and didn't they show that same exact clip in last week's "Previously" segment?). Bailey and Holly break up because he needs time to get over Sarah before jumping into another relationship.
Owen and Victor are having a conversation off-camera about whether Owen can wear his basketball uniform to school. Bailey sneaks in the front door and starts walking up the stairs. Just then, Victor, Will and Owen enter the room, so Bailey pretends he was just coming down the stairs instead. Owen is not fooled, since he noticed that Bailey wasn't in his room last night. Bailey says he was out, and Victor adds "at the gym." Will proves he is not the sharpest Crayola in the box by falling for it and asking Bailey why he went to the gym without him. I've said it before and I'll say it again: He is Steve Sanders. Owen asks why Bailey gets to wear the same clothes every day. Then, Owen reminds Bailey about his basketball game, and that his friend Hughley is supposed to spend the night afterwards. What the hell kind of name is Hughley, anyway? No offense to those named Hughley. Bailey pulls Victor aside and asks him to take Owen home after the game because he has to leave early. Victor asks if he has another all-nighter planned, and Victor and Will exchange "Bailey is a bad boy" looks. Bailey says he has dinner plans, and Victor and Owen leave.
Bailey and Will retreat to the kitchen, where Will asks if Bailey has spent the night in his bed once this week. Will continues, "I'm not judging you. I'm jealous." Bailey doesn't answer the question, and instead asks Will about some woman named Deborah. Will says that he and Deborah are taking it slow, plus Deborah's little sister is in town, which is putting a cramp in his so-called style. Bailey suggests that Will bring Deborah and her sister to the restaurant tonight, and Bailey can entertain the little sister so that Will can have some time with Deborah. Will says that the little sister is only eighteen, and thus off-limits to Bailey. ["No kidding, since Bailey is like thirty-eight at this point." -- Wing Chun] Bailey asks whether Will trusts him. Will says something about Bailey's being a "sex pirate" and "hoisting his sail" which doesn't make any sense. What the hell is a sex pirate? I swear, sometimes I think the writers just make words up and then throw them in the script because they know no one is paying attention. Bailey says that Holly was right, and that he needs to get out and relax, and prove to himself that there is more than one person for him. Will asks if that means he has to be with every woman in San Francisco. Bailey says that it might, but then says he's kidding, and hands Will the phone so that he can call Deborah. Will says that he and Deborah are "so close," and I guess he's referring to sex, but I don't see how taking her to Salinger's is going to seal the deal unless there is some sort of love potion on the menu. Bailey tells Will to trust him for about the third time in the last three minutes, so you know Bailey is going to do something bad. Plus, everybody wants to be closer to free.