 Having money problems, Sarah and Romy throw a singles party for profit in their apartment. During the party, after getting a letter from Bailey in San Francisco announcing their breakup, Sarah decides to do "something outrageous," with her now free-spirited life which leads her to drink, party, get a tattoo and consider spending the night with Spencer. Romy also becomes concerned about J.B. who becomes acquainted with a few too many girls that show up. Meanwhile, Maguire gets jealous when a musician friend of his, named Kenny, hits on Joss. Also, Cecilia becomes acquainted with an orthodontist, named Andy Beam, who shows a strong interest in her.