Awkward, self-conscious Adam Freeman has just finished his junior year of high school in 2006. When his cool older sister Casey suggests he visit her in New York for the summer, Adam has visions of meeting a girl and finally gaining some actual life experience. The fantasy doesn't materialize exactly as expected.
Casey has enthusiastically embraced life amidst Brooklyn's young LGBTQ community and invites Adam to tag along with her to queer bars, marriage equality rallies and other happenings. When Adam falls at first sight for Gillian, a smart, beautiful young woman in this new crowd, she mistakenly assumes he is trans.
Flummoxed and enamored, he haplessly goes along with her assumption, resulting in an increasingly complex comedy - and tragedy - of errors he's ill-equipped to navigate.