Would you keep dating your boss’s ex, or is that a big red flag waiting to explode?

Hey Lip and Shelby,

I need your help because this just got messy real quick. I work with a cool group, but everybody keeps their personal business tight. I’ve been dating this guy for three months — grown, respectful, treats me right… I’m really starting to fall for him. But I’m planning our company Christmas party, and boom — I find out he used to be in a long-term relationship with my boss. Like… YEARS. Now I’m sitting here wondering if I just walked into a holiday disaster.