Jack hires Betsy Frayne as the new security officer for the office, and Finch freaks out. Betsy went to college with him, and Dennis says she stole his personality. The Blush staff has Betsy thrown out of the building and fired, and are about to call the police when Dennis admits that he was the one who stole her personality back in college. Betsy is rehired, and now Dennis has to find another personality or settle with his dull (but true) personality, Denny, while Betsy confesses her true intentions of seducing Dennis. Meanwhile, Elliot forbids Jack from eating his cannolis after Maya and Nina accuse him of being Jack's bitch and Jack decides to get back at Elliot using his social influences, until Elliot can't take it anymore and gives Jack his last cannoli.

Elliot encourages Dennis to give Betsy a chance, since he thinks she's perfect for him. Although reluctant at first, Finch finally gives in and discovers the wonders of being in a healthy relationship. That is, until Betsy makes an inadvertent move on Elliot and proposes a threesome, which freaks Finch (and Elliot) out. Meanwhile, Maya struggles with the possibility of her father giving her special treatment when she asked for a raise and pretends she is leaving the magazine.