Open Wallet

Listen, you, PAIN. You're clearly not very smart, considering you needed a bear to explain this. Okay, so basically, Person A says that a woman looks good when her hair is down. Person B then says that A would look good when A starts spending money (opens his wallet). It's a playful jab at A's potential lack of funds or his tendency to be frugal. They're saying he would look good if he showed off his wealth, implying that looks aren't everything and that money matters more. Sheesh.