It doesn’t hurt to ask: You can be one question away from saving money. If you don’t ask for discounts, you’re missing opportunities to hang on to more of your hard-earned cash. It can be tough to muster up the courage, but it gets easier once you’ve done it a few times. You don’t have to be a tough negotiator. Be honest, undemanding and prepared for rejection. Many places offer unadvertised student, senior, military and employer discounts or will reduce the price if you buy in bulk, merchandise is slightly flawed, or if you’re a frequent and good customer.