Miriam, Derek, Ian, and Jenny are overachieving high school students doing everything by the book. Straight A's, sports, yearbook, band, and - when coursework allows - planning and executing elaborate murders.
Winnie, a dating blogger who anonymously writes under the pen name Luckless, goes viral for a post about a disastrous date with Holden, a perpetually single sports agent who refuses to settle. When Winnie’s boss offers her very own column on the popular lifestyle site, Mush, Winnie has no choice but to keep dating Holden for content. But things get complicated when feelings develop and Winnie learns that Holden has a teenage son.
After historic love letters start anonymously appearing in Kallie Sharp's mailbox, the hobby farmer searches for her secret admirer and opens herself up to love.