I've been divorced for about three years now and I still totally suck at paying bills.
I've developed a process that includes a giant fallen over pile and a check book. I sift for an hour and keep writing checks till there's no more money, then I try again in another month or two.
The problem is that I never paid the bills in my life. Ever. There was always a girlfriend or a wife that did it.
I don't think I'm genetically predisposed to pay bills. I lack the boobs and brain power to care. I've always been perfectly fine with "I'll make the money, honey. You go ahead and spend it. If you need some more, let me know and I'll get ya some more."
If we ever needed more money, I'd just get a job or do something else drastic like that.
How the hell does a guy develop a system to get this stuff done?
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Automatic online bill paying?
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There's a lot of software programs out there to help you keep track of bills, balances, etc. I can't remember any off the top of my head but I'm sure someone will jump in with some recommendations.
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"I lack the boobs and brain power to care"

You know guys can get boob jobs now...maybe that will help :-) As far as brain power I think you a screwed :-)
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Hmmm hire a maid. Clean house and bills paid.
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Quiken is a good software but you have to be willing to take some time at least once a week. A lot of it is automated but you have to help it out.
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I use Quicken and pay 99% of my bills online. Quicken reminds me when to pay bills.

I'm probably the exact opposite of you. I have always paid my bills and now pay all the bills my wife and I have. I am very anal about it. For some reason I have every receipt I've ever received since I was a sophmore in college. OCD anyone:-)
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I used to have Kerri do my bills. Trouble is, she really doesn't take them very seriously. After a few "stern reminder" letters came in, I kinda took back over so that my credit rating wouldn't be completely destroyed.
She helped me do them this morning and was a big help.
I don't need a maid, I don't mind cleaning at all. I actually prefer to do it myself so that stuff is actually cleaned. I'm pretty anal about stuff being all clean and orderly. I wish that'd spill over to my bill-paying thing. :-)
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:-) Very easy
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Just a little :-) I am the same way though...except the receipts.
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Also I want to point out that when I first looked at the title of this thread I thought it said:

I totally suck balls.

That is the only reason I came here. :-)
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My wife does the house account and I do the business account. We are totally the opposite. I know about how much money I have and about what needs to be paid. I have them all set up to be paid either out of the bank account or onto a points accumulating credit card. I pay the credit card off once a month and use the points I get for something fun. I never actually balance the checkbook, but I do look at it once a month just to make sure there is no funny business.
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I set up my bank to automatically send payment.
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You just need to practice, Scott.

Want to spend a few months paying mine? :-)
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Hehehehe.
I don't think you'd want me anywhere near your credit score. :-)
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Scott, we used to be constantly late with bills, but unfortunately we can't follow the procedure above alot of the time because we get paid bi-monthly.

So our process is:
1) Get a calendar with room to write in the box each day.
2) Upon receipt of bill, open it, and mark the payee and $$ on the date 7 days prior to due date on the calendar.
3) File the opened bills in order of due date (we use a hanging plastic file).
4) On payday, pay as many bills as possible, depending on the amounts.
5) Mail bill and check that day or next, or use online bill pay (we do online, when possible).

This all sounds complicated, but the initial setup takes an hour or so, and when a bill arrives, it takes a few minutes to mark it on the calendar. Depending on the frequency of your pay periods, it may take 1/2 to an hour to write checks or do the online payment thing.

This process is what got us out of our bad habits and having to pay those ungodly late fees that you get hit with now. Now we have the bills under control, and my wife or myself can sit down twice a month to get everything paid in advance of the due dates, normally with money to spare.

:-)
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I open all the bills when they come and put them in a pile according to the due date in my desk drawer. I don't have too many bills though so the pile doesn't fall over. I just make sure to check the pile every few days.....the next bill to be paid is on top and I know how close the due date is.
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I highly recommend MS Money or Quicken also. I have used MS Money for the past 8 years for my personnal accounts and use Quicken for my Home Business accounts.

Before I started using MS Money I was overdrawn alot and late on bills. Ever since I started using MS Money I have never overdrawn my account.
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I have an excel spreadsheet that I track all my purchases. This not only allows me to know where my money is being spent but also tells me when it's due. I separate all purchases into the following categories:

Groceries (self explanatory)
Gas (self explanatory)
Retail (includes general shopping and miscellaneous items)
Health (includes copays and prescriptions)
Entertainment (includes alcohol, cigars, and all my habits)
Bills (includes rent, water, electricity, etc.)

Using this spreadsheet I can tell where I need to cut back, ie. entertainment. It helped my wife and I transition to one salary. In fact just today while inputting my receipts I found out that a Mexican food place that my wife and I ate at last week overcharged me $20. I probably wouldn't have noticed this if I wasn't anal.
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Get a new wife?
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