In IT TAKES THREE, Cy (Jared Gilman), a quirky and bookish teen, is attempting a grand romantic gesture to ask his "dream girl" to the prom. This gesture fails, and a revealing moment is secretly filmed, posted online, and soon goes viral, much to Cy's humiliation. To add insult to injury, Cy, while walking with his best friend Kat down the hallway, must try to put up with Chris Newton, the best-looking and most popular kid in school, who is also a social media star with thousands of followers. When Chris tries to make fun of Cy for the viral video, Cy loses his temper and tries to fight Chris, and he's soon sent to the principal and sentenced to detention. While in detention, Cy meets Roxy, a new girl to the school, and Cy is immediately enthralled by her brains, charm, looks, and love of all things artsy. But when Roxy walks past the skatepark and Chris sees her for the first time, Chris is immediately smitten with her, and even more so when Roxy, unlike the other girls in the school, isn't taken in by his looks, personality, and celebrity. Desperate to win her heart at all costs, Chris enlists the help of Cy, who initially balks at the idea but soon agrees when Chris offers a large sum of money taken from the profits of being a social media star. Cy thinks the money will pay for the plastic surgery he wants to get to improve what he thinks is his unattractiveness. By posing as Chris on social media, and feeding him lines when Chris and Roxy eventually go on a date, Cy manages to present Chris as someone more arts- and literature-savvy than he really is. While Chris still finds ways to screw things up with Roxy, Cy finds himself to be more and more in love with her. Cy must decide if he'll reveal his true identity to Roxy, and must learn to see and value who he really is.