Paying bills is about as fun as a trip to the dentist. From your phone to cable to insurance, monthly expenses can shockingly add up to a small fortune. But a few phone calls and some old-fashioned negotiating can go a long way in helping you shrink your bills by as much as $1,000 a year. We tapped Kiplinger's Personal Finance Contributing Editor Elizabeth Ody for some money-saving advice, as featured in the magazine’s new iPad app. 
 
Start With Your Cell Plan

Since it’s one of our biggest monthly bills, there’s a good bit of room for savings. For starters, think twice about the size of your cell phone plan, says Ody. Do you really need unlimited? She continues, “Eight out of 10 of us overpay for cell phone service. So it’s a good idea to use a site likebillshrink.com that can help you find the best plan for your situation.” 
 
In fact, we waste more than $330 a year for unused text, minutes and data, according to researchers at BillShrink. Contact your carrier and ask about cheaper options that better reflect your usage. If you’re near the end of your contract, apply some pressure and let customer service know you’re considering the competition. Don't forget to specifically cite rivals and what they’re offering so your carrier knows you’re not bluffing!
 
If you’re in the market for a new service and are a light user, another option is a prepaid plan. T-Mobile, for example, has a 1,000-minute plan for just $100 a month. Or a monthly no-contract plan, such as Straight Talk, runs $45 per month for unlimited voice minutes, text and data. Potential savings with these changes? Up to $300 a year, says Ody.
 

 
Re-Bundle Cable

“If you’re paying a bundled price for your TV, Internet and/or phone service, you may see your monthly bill jump at some point once your so-called “introductory” rate expires,” says Ody. Her advice is to simply call your cable provider and say you’re unhappy with the new service and its cost. “If they feel you might leave, as opposed to paying the higher rate, you may be able to re-bundle, usually for a small processing fee, and get your rate back down to its lower level.” Ody says this, alone, can save you $300 to $400 a year.
 
And if you don’t have time to call, ask for a discount via online chat. For example, TimeWarnerCable.com and Verizon.com have 24-hour “virtual agents” that can answer your questions and even help to reduce your bill. 
 
Program Your AC  

Consider investing in a programmable thermostat. We featured The Nest in a previous Financially Fit video, which can keep your house cool without keeping the air conditioner on max all day. Changing your air filter regularly can also help your unit work more efficiently. Altogether, this could net you a savings of up to $200 a year.
 
Impress Your Insurers

Healthy living can convince your insurance carriers to offer a sweeter deal, starting with health. In fact, more medical insurance providers and employers are offering premium discounts to workers who quit smoking, lose weight or take part in wellness programs.
 
According to a recent survey by the Society for Human Resource Management, rewards or bonuses for completing a health and wellness program jumped from 23% in 2008 to 35% this year.
 
Car insurance agencies also like to know that you’re playing it safe. “Several auto insurance companies now offer breaks for safe drivers or for those who don’t drive much or drive during safer times of the day,” says Ody. Progressive, for example, has a program that lets you plug a small device into your car to measure these things. Drivers with the safest habits are getting discounts of up to 30%. That can save you $300 or more annually.
 
Auto-Pay Student Loans

You can cut your interest rate on federal student loans by 0.25% by opting for automatic loan payments.  Visit www.myedaccount.com to sign up. While you’re at it, make sure you’re on the right payment plan, as you have six to choose from, including income-based repayment.