Dip into your pocket Definition 1 of 3Pro Tip 1/3Personal Expense Used when someone pays out of their own funds, often voluntarily. For the team lunch, the manager dipped into his pocket. Pro Tip 2/3Generosity Implied Implies a generous act when one doesn’t necessarily have to pay. Even though it wasn't his turn, he dipped into his pocket to buy snacks. Pro Tip 3/3Not Business Typically refers to personal spending, not company expenses. Despite the company budget, she dipped into her pocket for better software.