Leigh runs the website Bad Date Chronicles, which allows people to post date experiences. When rival blogger Conner becomes the subject of one of her posts, they agree to date each other to see which one is the bad dater.
Aspiring screenwriter Clark Gable sees a chance for his big break when a movie, starring fabulous actress Helena Harris, comes to shoot in his small hometown. Clark manages to catch Helena's attention.
A well-known fashion photographer visits her hometown and reconnects with her former high school sweetheart. The dynamic duo pair up for the first time in years to compete in the town's centennial art competition.
Annie Butler finds huge success in her best-selling novel, but when her editor finds out that the very man she gushes about in the non-fiction story does not actually exist, she flips out and gives Annie a week to find him.