On the heels of Andrew and Zelda's great night together, neither is quite sure where they stand. With Stu's encouragement, Andrew goes on a date with a co-worker, during and after which Andrew and Zelda both try to play it cool. Meanwhile, Big Bird revokes her "no office hook-ups" policy and encourages all Wallflower workers to test the company's new dating app.
Things turn awkward when Andrew and Zelda each do some online snooping and discover secrets about the other that they wish they hadn't known. Meanwhile, Big Bird does some meddling on her own at Wallflower to shed some light on what fellow co-workers really feel about her and Stu teaches Stephie how to find the perfect guy in the world of online dating.
When Zelda's aunt suddenly dies, she struggles with the decision to invite Andrew to the funeral. Andrew tries to support Zelda through her grieving process and has convinced himself that she wants him there, but is afraid to ask. Meanwhile, Stu and Stephie vie for the attention of a musician at the funeral and Big Bird looks to trim the fat at Wallflower in her own special way.
Andrew and Zelda break with their respective traditions and decide to throw a joint Halloween party, much to the dismay of Stu and Stephie, who feel like they are losing their best friends. Meanwhile, with Big Bird looking for a solid promotional opportunity to boost the profile of the company, Henry takes it upon himself to enlist the help of Ray Parker Jr. to attend their annual Wallflower Halloween party.
Andrew wants to show off his tougher side to Zelda, but an incident outside a bar leaves her fending for herself. In an effort to right the ship, Andrew overcompensates to prove his manliness, and the results are far worse than he anticipated. Meanwhile, Stephie convinces Zelda to take on a big case involving Frank, a hunky farmer who is being bullied by a large biotech company, but her intentions to help extend far beyond his pending suit.
When Andrew comes across an old singing demo tape of Zelda's, she confesses that she struggles with her big "what if" in her life, believing deep down that she missed out on an opportunity to become a singer. In an attempt to bolster her confidence, Andrew helps her go after her missed dreams. Meanwhile, Stephie uses her mystic powers to help Stu and Big Bird share a new side of herself with everyone.
Andrew begins to realize his choices are heavily influenced by his friends, specifically Stu and Zelda. With Zelda's encouragement, Andrew confronts Big Bird about his stand on Wallflower's new business strategy, but his plan backfires when Big Bird promotes a young assistant Jordan in his position. Meanwhile, in an effort to have something all his own, Andrew tries to find a hobby he doesn't share with his friends.
As the holidays approach, Andrew and Zelda seek the help of their friends to find the perfect Christmas gift for one another. Andrew and Stephie come to a decision for Zelda seamlessly, while Zelda and Stu struggle on a gift for Andrew, spending hours shopping at the mall. Back at Wallflower, Big Bird faces a crisis when a longtime customer is set to interview with the local news about her unsuccessful matching experience. Also starring are Hong Chau, Parvesh Cheena and Katey Sagal as the Narrator. Ben Falcone guest stars.
Zelda sets up Stu with Jennifer, a stenographer from her office who she feels would be perfect for him. To Andrew's surprise, everything is going seamlessly with Stu and Jennifer, with the exception of Stephie, who feels like the fifth wheel. Andrew seeks help from Lora to match Stephie with someone at Wallflower so she doesn't feel left out.
Between the constant distractions of Stu, Stephie and her new boyfriend Joseph, Andrew and Zelda can't seem to get in any alone time. This causes some friction and Andrew and Stu start to look for separate apartments. Meanwhile, Big Bird recruits Lora for some girl talk as they strategize a way to get Dane to notice Big Bird.
When Andrew's father Pete unexpectedly shows up to visit, Zelda tries to win his affection after Pete tells Andrew he isn't a fan of hers. Elsewhere, Big Bird implements a new cancellation policy at Wallflower, despite not having Dane's corporate approval.
When Andrew's ex-girlfriend Madeline crashes at Andrew's while she is town, Zelda fears she is secretly after Andrew. Feeling threatened, Zelda decides to set up Madeline with an ex-boyfriend of hers in hopes of distracting her. Adding to her stress, Zelda contemplates a major career move.