
Boss, what's the best way to break up with someone without hurting her feelings? Hush money. What? Offer the dumpee a cashier's check for $5,000 on the condition she refrains from having hurt feelings. If she just can't do that, then you should be compassionate and offer her a $1,000 check as long as she agrees not to burden you with her hurt feelings. Very bad man. Compassion is an essential component of any severance package.