Eliza observes Henry’s constant bad mood and lack of skills with women and becomes determined to get him some action, whether he wants it or not.

When Eliza discovers that a distracted Henry wants to drastically reduce their mentoring sessions, she resolves to put an end to Henry’s biggest distraction -- his new lady friend, Julia.

For his fortieth birthday, Henry requests that Eliza find him a meaningful gift, but when she buys him tickets to see his favorite band, it creates tension between Henry and Julia, the woman he’s seeing.

When Eliza confesses her feelings to Henry, he avoids the subject by focusing on the company's annual karaoke party.

When Henry doesn't reciprocate Eliza's romantic feelings, a cold war develops between the two.

When Eliza's long lost sister Bethany arrives for a visit, she brings along unresolved issues. Meanwhile, Henry and Freddy's feud comes to a head.