This is the A-to-Z story of Andrew and Zelda — a pair that almost wasn’t — and all that happened from the day they met. When a computer glitch sends her a total mismatch, she’s asked to come in for an interview at the internet dating site where Andrew works, and this is where it all begins. Andrew and Zelda meet for the first time and despite their differences, sparks fly. She thinks it’s chance. He thinks it’s fate and is convinced she’s the shimmering girl in the silver dress he saw several years earlier.
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.
Zelda sets up Stu with a stenographer from her office, Jennifer (guest star SARAH BAKER - The Campaign), who Zelda feels would be perfect for Stu. To Andrew's surprise, everything is going seamlessly with the new couple - except Stephie feels like a 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 (Henry Zebrowski), Stephie (Lenora Crichlow) and her new boyfriend Joseph (guest star Echo Kellum), Andrew (Ben Feldman) and Zelda (Cristin Milioti) 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 (Christina Kirk) recruits Lora (Hong Chau) for some girl talk as they strategize a way to get Dane (guest star Wayne Wilderson) to notice Big Bird.
When Andrew’s (Ben Feldman) father Pete (guest star Dan Lauria) unexpectedly shows up to visit, Zelda (Cristin Milioti) tries to win his affection after Pete tells Andrew he isn’t a fan of hers. Elsewhere, Big Bird (Christina Kirk) implements a new cancellation policy at Wallflower, despite not having Dane’s (guest star Wayne Wilderson) corporate approval.
When Andrew's ex-girlfriend Madeline (guest star Dreama Walker) 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.