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« Interview with Stuart Lucas Author of Wealth, Part 2 | Main | How to Make Money: Sell Your Stuff »

June 20, 2006

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Usually when people do that, it is because they really want to go someplace with you but don't want to make it a burden on you, so they pay for you so that you can go with them. So unless it's some kind of pathological condition, or you feel indebted to them or they are getting themselves into debt on your account, then I would not get worked up over it. And who says that your friend has to do all the scheduling? You can pick a place that you can afford, and tell them at the beginning of the meal that it's your treat. I think that Kiplinger's suggestions about non-financial ways to treat them is a little like you are working for your meals - I wouldn't jump all over my friend to let me cat-sit unless it was something that we did for each other.

I think I have a touch of that bug though, since I really love buying presents for people or bringing them home "a little something" to the point that in college my boyfriend started gaining weight. And it's never about being even, and I don't expect others to give things to me, I just like to do it because I like to see them be happy. Hell, half the time I would prefer that they not know who gave it to them!

I'm on the opposite end of this situation, I think. But in my case I tend to think of it kind of in terms of karmic repayment. The same friend, during the 4 years I spent perpetually broke and often near-suicidally depressed, helped me out immensely, with both money and time that she couldn't necessarily afford. Now that I've put my life back together and am making money like crazy (and financially, she's frankly not doing so well), it's just fair for me to pay for stuff.

How about your wealthy friend who thinks everyone else is obliged to pay for him? I've known this guy for a long time and it's always painful - I've had to say things like: 'people keep money on them to pay for drinks or cigarettes' numerous times. In his mind, wealthy people don't carry cash & everyone else has the obligation to pick up the tab. When I explain that I know no wealthy old men who would ever let me pay for lunch, it makes no impression. He's expensive as a friend and haughty about having a well-off family at the same time. He's a charmer outside of this screwed up take on the world's obligation to make him richer one drink/smoke/lunch/dinner/etc at a time.

What is even more awkward is the wealthy friend who always wants to go out, but doesn't pay. You end up turning them down all the time because you can't keep up with thier lifestyle.

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