We meet Jeremy, a young actor in search for a normal life, and Sheila, a mother on the brink of a nasty divorce, we dive into Jeremy's adventurous move into the big city. When Sheila needs help paying the bills and Jeremy needs space from his Mom-ager, they decide moving in together is the best solution.
Jeremy settles into his new apartment and needs to find a job. He and Sheila brainstorm ideas for The Hobbit for All Seasons; the ultimate fanfiction pairing of characters.
Sheila has a disastrous mediation with her ex and Jeremy meets Dennis, which Sheila worries may prove equally disastrous.
Sheila and Jeremy enter a fan fiction competition, attend New York Comic Con and look for love...in all the wrong places.
NY Comic Con calls and Sheila and Jeremy answer! Sheila attracts both welcome and unwelcome attention and Jeremy makes a difficult choice.
Jeremy and Dennis move close to...something, while Dan and Sheila reach an agreement.
Jeremy comes to a decision regarding his job offer while Sheila drives right off the cliff following her mediation.