Eliza gets a confidence boost when she learns that her new female role model/former middle school bully used Eliza's life as an inspiration for her success. Henry is determined to rid himself of his childhood poser status by finally teaching himself how to ride a skateboard.

Eliza's long lost sister Bethany arrives for a visit and with her brings a host of unresolved issues that challenge Eliza's progress. Meanwhile, Henry attempts to beat Freddy in the company's Tough Mudder for charity, and their long-simmering feud comes to a head.

In the aftermath of Henry not reciprocating Eliza's romantic feelings, a cold war develops between the two-until Eliza's financial crisis and her need for Henry's advice brings hope of detente.

Eliza decides to confess her love for Henry. She tries to get Henry to confess his feelings for her, but ends up making things awkward for the two of them.

Eliza's effort to "follow through" on a work idea impacts her relationship with Freddy. Henry rejects an admirer, leading to unexpected consequences.

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 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.

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.

Eliza and Henry spend the weekend at the Saperstein's estate but with zero cell reception and a prospective promotion being dangled in front of them, both Henry and Eliza exhibit some questionable behavior.

Eliza accepts Henry's challenge to do something helpful over the weekend and reluctantly offers to babysit Charmonique's young son on a Saturday night. Little does she know that young Kevin has a lot to teach her about having fun.

Henry and Eliza discover that their most valuable office relationship might be their own after Saperstein mandates his employees to work on their interpersonal connectivity.

Eliza's fling with her co-worker Freddy gets complicated, and Henry explores Facebook for the first time with disastrous results.

Social Media superstar Eliza Dooley has 263,000 followers who hang on to her every post, tweet and selfie. But after a workplace mishap goes viral, she quickly realizes that being "instafamous" isn't all it's cracked up to be and being friended is not the same as having actual friends. She enlists co-worker and marketing guru, Henry, to 'rebrand' her self-obsessed reputation and teach her how to connect with people in the real world, whether she 'likes' it or not.