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.