Most people treat the price tag like it’s a law of nature. It’s not. In most cases, that number is just a suggestion—a “starting point” for the conversation.
If you’re not negotiating your recurring bills, your big-ticket purchases, and even your medical expenses, you’re essentially leaving a pile of cash on the sidewalk.
I’ve spent years haggling over everything from hotel rooms to hospital bills, and I can tell you: the “ask” works more often than it doesn’t.
In fact, a 2025 survey found that roughly 60% of people who reached out to negotiate their medical bills achieved a lower price, and more than 90% had at least partial success. That’s more than a coin flip’s chance of saving hundreds, or even thousands, of dollars.
Here are the golden rules for keeping that money in your pocket where it belongs.
What costs can you actually negotiate?
The short answer: almost anything where a human being has the power to change the numbers.
1. Medical Bills: This is the big one. Between “upcoding” and simple human error, medical bills are notoriously messy. Don’t just pay them. Ask for an itemized bill first to spot mistakes like duplicate charges. (See Master These 10 Negotiating Steps to Crush Your Medical Debt)
2. Monthly Subscriptions: Your cable, internet, and wireless providers are desperate to keep you. The cost of acquiring a new customer is way higher than the cost of giving you a $20 monthly discount. (See 7 Ways to Negotiate a Better Cable Package)
3. Large Purchases: If you’re buying appliances, furniture, or a car, the sticker price is a fantasy. Even at retail stores, floor models or slightly scratched items are prime targets for a 10% to 20% discount. (See Confessions of a Serial Haggler)
4. Credit Card Interest: If you’ve been a loyal customer and your credit score is decent, call your issuer and ask for a lower APR. They’ll often drop it just to keep you from transferring your balance elsewhere.
5. Hotels: I don’t remember ever checking into a hotel and not asking for a better deal, either on price or for a free upgrade.
Negotiate more than just the price
Sometimes the person on the other end of the line really can’t budge on the dollar amount. That’s fine. Don’t walk away yet. There’s a whole world of “value” that isn’t reflected in the base price.
1. Timing and Delivery: If you’re buying furniture or a major appliance, ask them to throw in free delivery or a haul-away service for your old unit. That’s a “hidden” savings of $50 to $150.
2. Payment Terms: Can’t get the price down? Ask for an interest-free payment plan. Or, flip the script: offer to pay the full amount in cash right now for a “prompt payment” discount. Many medical providers will shave 10% to 20% off the total if you settle the bill on the spot.
3. Extras and Upgrades: When booking a hotel, ask for a free room upgrade or late checkout at the front desk. The worst they can say is no, and during off-peak times, they’re often happy to accommodate you just to be nice.
When is the best time to strike?
Timing is everything in the world of the deal. You want to negotiate when the seller is at their most vulnerable—or their most motivated.
1. The End of the Month: Most salespeople have quotas. If they’re two sales short of a bonus on the 30th of the month, they’re going to be a lot more flexible than they were on the 1st.
2. The “Slow” Season: Try buying a lawnmower in October or a snowblower in April. When demand is low, your leverage is high.
3. Before You Buy: For medical procedures, ask for the “insured rate” or a cost estimate before the service. Once the service is rendered, you’re a debtor; before it’s rendered, you’re a customer. Customers always have more power.
The secret sauce: How to talk the talk
You don’t need to be a “shark” to win. In fact, being a jerk is the fastest way to get a “no.”
First, do your homework. Know what the competitors are charging. If the dry cleaner down the street charges $2 for a shirt and yours charges $3, ask them to match it.
Second, find the right person. The teenager behind the fast-food counter can’t change prices. You need a manager or someone in the “retention department” (for bills) who actually has the authority to hit the “discount” button.
Finally, embrace the silence. Make your offer, then shut up. Let the other person fill the awkward gap. More often than not, they’ll come back with a counter-offer that’s better than the original price.
It might feel a little weird the first time you do it. Get over it. That “weird” feeling is just the sound of money staying in your bank account.
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