Inspired by My Fair Lady, "Selfie" tells the story of a self-obsessed twentysomething woman who is more concerned with "likes" than being liked. After suffering a very public and humiliating breakup, she becomes the subject of a viral video and suddenly has more social media "followers" than she ever imagined - but for all the wrong reasons. She enlists the help of a marketing expert at her company to help repair her tarnished image.
Eliza's fling with her co-worker Freddy gets complicated, and Henry explores Facebook for the first time with disastrous results.
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 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.
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.
Henry's constant bad mood and lack of skills with women are observed by Eliza and she starts to become determined to get him some action, even if he does not want it.
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.
Eliza's effort to "follow through" on a work idea impacts her relationship with Freddy. Henry rejects an admirer, leading to unexpected consequences.
Eliza confesses her growing feelings for Henry, who avoids the subject by focusing on the company's annual karaoke party.
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'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 defeat Freddy in the company's Tough Mudder for charity, and their long-simmering feud comes to a head.
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.