Surviving you first break-up can be tough, especially when you wish everything would stay still forever.

Winnie Dawson is a classic, charming, stay-cozy kind of girl. When her boyfriend Jesse, who also happens to be her best friend, breaks up with her after their high school graduation, her plans for the future turn uncertain and scary.

Looking for a change of scenery, a trip to Chicago turns out to be exactly what she needs to make things better. Especially after some unexpected encounters... a stray kitten, a famous influencer and an old middle-school crush.

Winnie documents her summer in a polaroid collage as she tries to move forward leaving behind the boy who broke her heart while trying to remain best friends with him as much as she possibly can.