Too Wicked for Love

My boss is a billionaire, playboy, and former hardened criminal all rolled into one...

...while my mother is notorious for being conned by rich handsome crooks.
I know things like 'heartbreak' and 'poor' taste in men aren't supposed to be hereditary, but the moment my wickedly dangerous boss says he's attracted to a shy nerd like me---
We all know how this is going to end, don't we?