Relationship expert Andrea Syrtash tells Jordan Carlos how to tell if you should date your friend’s ex. Start by doing a cost benefit analysis, what’s the cost if you do or don’t. Are you looking to put a ring on an acquaintance’s hookup? Or are you looking to hookup with your best friend’s ex-wife? Always make sure the lady reciprocates before you break the news to your bro. And when you tell him, don’t ask permission, that makes things even more awkward than they already are.