A young gay high schooler named Brendan visits New York City for the first time with his mom. To him, it is his first taste of freedom in his desire to escape Missouri, live in an actual city, and meet Tom, the New York-based law student with whom he's had an online relationship. Brendan has typical teenage responses to his mom's hat and her fanny pack and claims that she is afraid she will get shot in the city. But, when he sees the bill for the restaurant they go to for dinner, he is scared of the prices and wants his mom to walk them out. She doesn't say anything, much like she has nothing to say about his desire to visit Tom alone. Brendan feels terrible for being so harsh that day, but his temper flares again when she refuses to walk into Central Park for fear she will be attacked.

The day he goes to meet Tom, Brendan agonizes over his outfit. Brendan walks to the apartment building alone and thinks about the money he has paid for the date/sex, supposedly to help Tom pay for college. He's let into the apartment and sees who he expects to see based on the pictures online, but the apartment feels fake. Tom flirts with Brendan and acts coy about being in law school. In the bedroom, Brendan notices there is mail for Greg, but he brushes it off. Tom enters after smoking something from a pipe in the other room and explains that the "Tom" profile is fake for people who want to pretend. Brendan asks if he can pretend, too, and they kiss.

As he heads home on the bus after the hook-up, Brendan notices that the strip malls and houses on the city's edge look much like those he left in Missouri. His mom asks him how the visit was when he gets back, and when he gives a noncommittal answer, she tells him she'll always love him, no matter what. Brendan leaves rather than let her see him cry.