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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.