Laurel gives Megan the task of chaperoning the twins' pool party, thus forcing her to cancel plans for a spa weekend with Jacob. Meanwhile, Charlie confesses to Marco that he is in love with Megan, and Megan is convinced by Rose to invite Lily to the pool party.

Megan becomes more uncertain about where she stands in her growing romance with Will when he claims to have dated a lot more that she has, So, Megan asks Charlie's latest girlfriend, Mandy, to set her up on a blind date with one of her co-workers. Meanwhile, Rose gets a 'D' on her English exam and plots to keep herself from failing her upcoming history exam by stealing a copy of the test, and Sage devises a crafty plan so Rose will not get caught. Elsewhere, Laurel confides in Megan about her long-lost romance with her one-time boss, while Megan also learns that Lily is now dating her irresponsible punk boyfriend again.