Dear Mrs. Riches,
I have a friend who's becoming a pain in the finances. He doesn't exactly ask to borrow money but is perpetually broke, so whenever we go out, guess who foots the bill? I'm getting tired of his excuses but still like the guy. Got any advice?
-- Empty Moneybags

Dear Moneybags,
Try setting boundaries as a first line of defense with your favorite mooch. It doesn't have to be a big fight. Suggesting a low-cost alternative is a good strategy ("Since we're both broke, let's stay in and catch the game"), as is using humor ("Frankly, I can't afford to go out with you!").

Before you make plans to go out the next time, say something like, "Just so you know, I'm low on funds so I can't cover you anymore." When the time comes to pay up, if he doesn't have the money, don't offer to pay his way. Make natural consequences work for themselves. After a few times of testing your resolve, he'll have to give up on going out or cough up the money.

If talking and natural consequences are a bust, you may simply have to choose to take a break from going out with your friend. As much as you like him, you may have a chronic mooch on your hands.

Dear Mrs. Riches,
I have a dear friend who is obsessed with the cost of things. She is always emphasizing the bargains she finds and that things that look expensive were actually "dirt cheap." For example, if I say, "Nice blouse. Is it new?" the response will always include the price of the item (e.g., "Yep, only $9.99 on sale at Ann Taylor. Can you believe it?") It's gotten to the point where I don't want to say anything nice for fear of hearing all about the latest shopping coup. It's just not all that interesting to me. Any helpful words would be appreciated.
--Bargain-Fatigued

Dear Bargain-Fatigued,
Is it possible that, because of your previous reactions, your friend thinks you are very interested in her discourse on bargains? Maybe she simply hasn't caught on that your interests have changed. If that's the case, try changing the landscape of your friendship -- suggest a new activity the two of you can try (one that doesn't involve shopping!). Take a class together, embark on a shared goal like training for a marathon or reading the classics -- in short, anything that may invigorate a stale friendship.

If that isn't the problem, look more closely at your friend and how she is doing. Is it possible that she's acting out of old insecurities about money and isn't aware of it? Has she turned to shopping for fulfillment because she's unhappy with the rest of her life? These are just a couple of the more deep-rooted explanations for her behavior. While identifying these may not solve the problem for you, at least they may supply greater understanding and insight. They may also nudge you to offer her support, rather than simply becoming annoyed.

In the end, friendship is a choice. You have to decide whether or not you can tolerate her foibles in return for the enjoyment you get in her company. But don't be too quick to throw out an otherwise good friendship because your friend has an annoying habit. After all, who knows what she's quietly tolerating about you!

Got a friend who's always looking for bargains or who's struggling to get out of debt? Send them to The Motley Fool's Living Below Your Means board for advice, support, and a better financial future today.

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Fool contributor Elizabeth Brokamp is a licensed professional counselor who regularly talks money with her honey, Robert Brokamp, editor of The Motley Fool's Rule Your Retirement newsletter. To get your money and relationship questions answered, send her an email .