Jane Grabowski hauls herself to her nine to five office job at New York City's most acclaimed newspaper to sit in stale air under severe florescent lights and mask her rage by sending emails with too many exclamation points.

Luckily, Jane has a reason to keep coming into the office: Madeline, the distractingly beautiful intern. Madeline has never dated a woman and is uncomfortable with labels but with carefully timed lunch breaks and painstakingly crafted texts, Jane works her way into her life. Meanwhile, Jane's free-spirited artist roommate tries to keep her from falling for a straight girl by dragging Jane to gay bars and queer Shabbat dinners, where she meets the decidedly uncool and morally righteous musician, Addy.

Caught between Addy's readiness to commit and Madeline's alluring unpredictability, Jane is pulled down a slippery path of lies and deceit, leading to a plane ticket that threatens to take everything down in one fell swoop.