Vacation When I Fell in Love with You

Winnie Dawson has everything planned: finish school, move to Chicago, and enroll in college with her boyfriend Jesse. But he has other goals and suggests taking a "break" in their relationship. This breaks Winnie's heart. Taking her Polaroid camera, she heads to Chicago to explore the city before classes begin. On her journey, she meets a homeless kitten, a popular blogger named Lila, and her first love – Robin. Should she wait for Jesse to decide to resume their relationship? Or can she trust the butterflies in her stomach that appear at the sight of Robin? And will Winnie manage to handle this without breaking her heart again?