Micah Summers runs a popular Instagram full of drawings of his numerous imaginary boyfriends (ninety-nine so far)—though he's never had a real boyfriend before. But when a meet-cute with Boy 100 goes wrong, Micah embarks on a Prince Charming-like quest throughout Chicago to find true love - for real this time. Will Boy 100 be the One? Micah is rich, dreamy, and charming. As the “Prince of Chicago”— the son of local celebrity sports radio host known as the King of Chicago—he has everything going for him. Unfortunately, he’s also the prince of imaginary meet-cutes, since he’s too nervous to actually ask boys out. Instead, Micah draws each crush to share on Instagram with a post about their imaginary dates. Ninety-nine “boyfriends” later, his account is hugely popular, and everyone is eagerly awaiting Boy 100. So is Micah. He’s determined that Boy 100 will be different. This time, Micah will sweep the boy off his feet, for real! So when Micah flirts with a hot boy on the L who’s wearing a vegan leather jacket and lugging a ton of library books, he is sure this is Boy 100. But right before he can make his move and ask for the boy’s number, the guy rushes off the train, leaving behind his pumpkin-embroidered jacket. The jacket holds clues to the boy’s identity, so Micah and his friends set off on a quest to return it. Along the way, Micah will discover that the best relationships aren’t fairy tales. In fact, the perfect fit—and true love—might be closer than he thinks.