Megan comes running into the kitchen to tell Marco that her best friend from Yale, Caryn (Sarah Drew), was coming to visit.  After Marco seems less than exciting, she tells Will who came over for his usual breakfast.  She asks will to take them out on one of his yachts, but he's working.  Wait, what?  That's right, Will has a job as a gopher for a sports photographer and he scores the ladies some tickets to the match.

Luarel comes in to interrupt Megan and Caryn to talk to Megan about the girls' progress reports which she thinks Megan kept hidden from her.  She also tells Megan she never gave her permission to have a houseguest.  Caryn meanwhile had a much better conversation with her boss who called... she got a promotion.  Caryn offers Megan her old job.

Megan and Caryn arrive at the tennis match and are talking about Will and are overheard by his boss, Peter.  Megan accidentally tells Peter how rich Will is.  When she goes to talk to Will she distracts him and makes him miss a key hit.  Will is very upset that Peter knows he's rich and feels he will be treated differently now.

At home Megan sets up some cucumber water and snacks for the twins' study session but they blow it to meet with their new stylists.  With time off, Megan and Caryn decide to make it a girls night and go to clubs where they just wait in line, give up, and head home for takeout.  Caryn suggests Megan write an autobiography.

Will meets with Peter to show him the photos and Peter is way friendlier than usual.  He doesn't even allow Will to get him coffee.  Megan goes to whine to Marco about her job and he tells her it could be worse, Will lost his.  While Megan helps Caryn pack, Cary tells Megan she pitched her story to her boss and her boss loved it.  Megan says she's not going to write a story and sell out her bosses.

The next day as Caryn sneaks out to leave, Megan runs into her and the girls make up.  Megan has a little sit down with Laurel and offers to quit if she wants her to.  Laurel says no, she's hope she is the Megan she first met.  Will comes over and tells Megan, he wasn't fired because of her, he quit.  She tells him she's going to help him with a resume and job hunting and she shuts her up with a kiss.  Scratch off Smith daughter number two.  Which family is next stud?

Rose and Sage's Career Begins
The twins meet with their publicist Patricia (Kathy Najimy) and tell her about their singing / guitar skills and give her a demo tape.  Rose is strugglign with Ernest Hemmingway's A Farewell to Arms while Sage blows through it.  Patricia calls them with news they're doing an opening for a night club the next day.

Rose and Sage have a very successful set at reherasal and Patricia gives all the credit to Rose.  Sage, you might want to actually play that guitar you bragged about and not bass next time then.  Just saying.  The girls show up on the red carpet for the event and Patricia introduces them to Perez Hilton (playing himself).  Rose freezes up when it comes time to talk to him and Sage steps in.

Back home, Sage falls right asleep while poor Rose still has to finish a Farewell to Arms.  She picks up the book and falls asleep after a few words.  The next day at their final and Rose stares blankly at the page while Sage, of course, rocks it.