Stella Allen is a normal girl living in New York city with her best friend. She works at a local coffee shop and doesn't like getting into trouble, not even with boys. She doesn't want to get hurt by them, so she has one rule for dating. She need 100 reasons why she should date the guy. Now that is hard. But, what happens when her cousin's best friend sweeps her off her feet and agrees to tell her 100 reasons why they should date?