Generosity or Stupidity?

Photo: Mike Schmid

I have a friend who would cut off his right arm if it could help a complete stranger in their time of need. Okay, so maybe this is a touch of an exaggeration, but in truth it’s not far off the mark. And with this level of generosity unassumingly extended to strangers, you can only imagine how far he’ll go for a friend.


He has a daughter he supports from afar, and although the agreement with his ex-wife is more than fair, he regularly sends far more money than is required, even though he is still swimming in the debts of their marriage (having taken it all on his shoulders unnecessarily).


Although I don’t believe he has ever come completely clean about his financial situation, I know enough about it to know he has no business treating groups of friends to fancy meals, and generally spending money like it is nothing. We all try our best to contribute, but he makes it impossible to do so and will actually become belligerent about it at times. He’d rather throw our money on the ground and walk away from it than let us pay. (We have of course learned to deal with this by not going out to dinner with him, but he still manages to find ways to spend money on us).


He is not the only person I know like this. I have known a few people who, despite meager finances, will attempt to foot the bill for everybody at dinner, saying with a flippant shrug that we can “catch them next time”. But when next time comes around, the story often changes and we manage to repeat the same charade.


As a frugal person (and one who has gone through times when money was scarce to non-existent), I don’t understand the rationale behind this generosity. I’m not stingy by any stretch, but if I didn’t have the money, paying for everybody didn’t even cross my mind. In fact, if I didn’t have the money, I just didn’t go out. Period.


So the question is this: At what point does generosity cross a line and become stupidity? In truthful moments, I have questioned the actions of my generous friends, and in some cases they admit it stems from unhappiness. If they have to plod their way through yet another week without a treat or something to look forward to, they would…they would…well they don’t know what they would do, but it would be bad. They lose the ability to maintain perspective through it all and can only see as far as the next day.


I understand that.


But…is my friend actually crippling the efforts of his ex to support their daughter by sending so much money that she becomes improperly dependent on it? Is he over-spoiling his friends by paying for dinner? I have already found that certain friends of his have learned to take his generosity for granted and he’s starting to fight feelings of inequality in their friendships, causing the friendship to suffer overall.


And are there not other ways to be generous that don’t send bank accounts further into the red?


At what point do these actions cross a line and become over-generous? And when it comes at the expense of our own financial health, is it generosity – or stupidity?

Average: 1 (1 vote)
Your rating: None

Disclaimer: The links and mentions on this site may be affiliate links. But they do not affect the actual opinions and recommendations of the authors.

Wise Bread is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to

Guest's picture

I am your pal to a point. I love picking up the dinner check. It elevates the mood and continues the camaraderie. The difference between me and your friend is that I only carry a student loan and a mortgage and though my income is lowish, I can afford it. It's my luxury, my reward for hard work. Also, we're mostly talking restaurants that serve burgers.

I've also come to recognize friends who take advantage. I'd like to be more altruistic in my giving, but once I identify them I will no longer foot the bill until they pull out their wallet at check time. Recently, I had a pal who is good at reciprocal giving and a pal who has never once paid at the same restaurant table. The giving friend and I paid more than our share of the bill and the tip. When we pointed this out my stingy pal made no indication of understanding our request that she cough up the dough! I love my stingy pal and want to spend lots and lots of time with her, but no more free lunches at my expense.

Guest's picture

It sounds like your friend feels guilty for the breakup of his marriage or for not seeing his son regularly. It's pretty common for guys in that situation to try to "buy" their child's love, not because they think they can, but because they feel guilty that they aren't able to give them the "happy" childhood they deserve. This will probably change once your friend becomes involved with another woman :)

I know what you mean about generous givers though. My husband tends to be like that. Personally, I don't like "owing" favors and having to keep track of whose turn it is to buy things. Plus, I don't think it's something people who are in debt can really afford. Why can't we all just pay for ourselves?

Guest's picture

This behaviour sounds controlling and manipulative to me. Behind a veneer of altruism, he's plastering over some deep psychological wounds, e.g. a low sense of self worth. Like Finance Girl said, some guys try to buy the love of their children. He could be trying to buy friendship, or paying his ex not to bad mouth him.

But when push comes to shove, when he throws your money back in your face when you try to pay your own way, he's still controlling your behaviour to fill his own neurotic needs. It's no wonder that some of his friends are taking advantage. He's setting himself up for co-dependent relationships.

Guest's picture

Many years ago, I treated friends when I was busted, on my credit cards. I understand now I was grateful for attention and friendship - and thought I had to pay for it somehow, to show my gratitude for the time spent with me.

Guest's picture

It sounds like he has low self esteem and that he's not much fun to be around.

I agree with Jo that it's controlling. Probably not consciously so, but your friend is trying to make himself feel better by being seen as the big man and is ignoring the fact that it makes everyone else unhappy.

He may refuse to 'get' that this behaviour is disliked, but it will almost certainly cause him to lose friends. You could try explaining it to him, but I wouldn't hold out much luck.

Guest's picture

It's certainly a malfunction of some sort. Probably compensating for feelings of self-doubt or uncertainty. Of course it could be part of his upbringing. My grandmother is generous beyond compare (though not to self-detriment), but we always have the opportunity and responsibility to politely decline.

I don't believe that adults can be 'spoiled' by others. If we take abuse another's generosity, we're at fault. We all have to take responsibility for our own shortcomings, I think.

Guest's picture

I used to do this with my friends all the time. Then someone suggested I seek treatment for depression. After some deep introspection (and medication) I was able to gain perspective on what I was actually doing. I was trying to get people to like me and like being around me. The same was true at Christmas time; I would buy extravagant gifts for everyone I knew, often for those that couldn't buy anything in return. I didn't expect anyone to reciprocate, I just wanted them to know I wanted to be friends.

Years later, I see some of my friends that do this same thing, whereas I've adopted a more frugal lifestyle. It took a long time, but I eventually realized that if people don't like me for who I am as a person, I don't need them in my life. I don't need to "buy" acceptance any more. My closest friends are the sort of people that can have a relaxing pot luck at my house rather than splurging at a resturant.

My best suggestion would be to have an honest conversation with this fellow. If he wants to pay, gently remind him that you like to pay your own way and you don't want to take advantage of him. If he insists, be firm. If he puts up a fight, look him in the eye and tell him No. Reassure him that paying your own way doesn't change your friendship. It will begin to sink in eventually, and he will respect you more for it in the long run.

Guest's picture

"Wealth is better than poverty, but only for financial reasons," quipped Woody Allen long ago.

It's so easy to lose one's balance in a hyper-commercial, super capitalist culture. Ads bombard us daily with the message that we are what we own. If we feel depressed, lonely, or overwhelmed, it's easy to believe that money can buy us friendship, if not love. Your friend's behavior probably flows from this belief system.

Your suggestion of finding other ways to express friendship hits the mark. Perhaps one could suggest/schedule long walk-talks to provide an alternative way to show appreciation and be together without financial obligations. Showing, instead of telling, might be more effective here.

On the other hand, I'm a rather live and let live and speak and let speak guy. Your friend might also need to be feel like a "winner" by picking up a bill - even if on a credit card - while he struggles with other financial issues. As a friend, I tend to offer sympathy and understanding while avoiding harsh judgments without knowing all the relevant facts. After all, in a world where over a billion people live on less than a dollar a day, we are all quite wealthy in the big picture.

Guest's picture

At the expense of my financial health=stupidity.

the bills must be paid LOL!

Guest's picture

Perhaps he believes that he's so far in debt that "one little meal for friends/a few more dollars for kid/etc" can't make it worse.

I like the suggestion of activities where no money is involved.

Perhaps you could also suggest meeting at coffee shops or restaurants where food is served cafeteria style and everyone pays their own bill before sitting down.

Guest's picture
Paul Kimmel

I'd have to agree with the person who said, "neither generosity nor stupidity." It's dismissive to even raise the question of "stupidity," since you obviously don't believe your friend is stupid. If you want to congratulate yourself for the things you've figured out, fine, but certainly you can find a better way to do it. The word "stupid" doesn't even apply.

Almost everyone has "issues" around certain things: food, sex, money, work, etc. And only once we stop to examine the lessons we learned while growing up will we ever grow beyond our habitual patterns of behavior. Whether his behavior is manipulative, altruistic, or simply short-sighted is not a call anyone here (yourself included) can make. The only things we can say for certain is that it looks like a bad habit, and with daily practice it could be changed.

I think the real question is this: what unexamined behaviors do we have when it comes to generosity? The question might be better phrased as, "What do we get from giving?" Once we figure that one out, then we'd be able to discern when we've gone too far.

Guest's picture

We have a friend similar to this guy... It does get old when you must battle over who pays for what, etc... It is an ego thing with our friend, and he takes it to the wall every time. He even goes so far as to get money from his girlfriend (who does not have it to spare) to throw around and play the "big-shot."

He loves to brag about spending money on other people, and makes up stories to tell us about it... I feel bad when he does this because we all know the stories are more fantasy than reality. He has seen a therapist who advised him that he has low self-esteem, and tried to help him work on it. He now declares that he was totally "cured." He is impossible to reason with.

However, this guy is really a decent man, and a true blue friend. So we tolerate his quirks, and try to gently steer him in a sensible direction when we can. He will allow us to pay for meals part of the time. We will never abandon him since we're about the only friends he has.

Guest's picture

As the only poster who likes to routinely pick up the tab, I feel compelled to emphasize a few things.

First, how one person (mis)spends his/her money is his/her own business. If you are uncomfortable having a friend pay for your dinner, pay for your own. That's pretty simple.

Second, paying for someone's dinner does not mean that you are trying to control them or that you have low self-esteem. I pay for a variety of reasons. Sometimes it's because I know my financials are more sound. Sometimes I pay to express my gratitude for friendship (I am not a gifty-type person and so this would encompass special occasion gifts). Sometimes I pay to get out of the restaurant quicker. Sometimes I pay just because.

Third, I don't keep track of who pays when. I know it shakes out and I feel like bean counting ruins the point of giving.

In any case there is a big difference between my desire to pick up the tab and your friend's and that is that this is my one guilty pleasure and I do it with cash in hand.

As a side note, whatever his reasons are for supporting his daughter in excess of the court order, it's his kid. Distance fathering has to be difficult and if the extra dollars his kid's way make him feel better about parenting, more power to him. I would do it differently (save the money to fund face-to-face visits), but I'm not him.

Guest's picture

Any good thing if taken to its extreme can be harmful. Extreme generosity is not healthy for the giver or the receiver of the gifts. Explaining this balance to your friend is important but getting him/her to grasp it may not be so easy. A person who is unable to balance the financial aspects of their life may have emotional issues that are the root cause (in this case therapy can be very helpful) and they may not (in this case being firm with your friend may be the solution). It isn't easy to change someone so I recommend just being a good friend to them and doing your part to boost them up emotionally while not draining them financially.

Guest's picture

People that give away money are happier...

Guest's picture

I used to do this, in a more limited fashion, in my case it was linked to denial of my situation. Looking back it was obviously pretty stupid & ultimately extended the period I was paying off my debts considerably.

I will say in my case though it proved an essential step in the road to being financially sensible and an adult.

Guest's picture

I have this problem with my own parents. My sister and I are both grown, yet they still send us sizeable checks for birthdays and holidays - and I'm pretty sure that I earn more than both of them combined. If I don't cash a check, my mother gets terribly insulted. It's not worth the argument, so I just take it and figure out a way to subtly repay them.
They also always "lend" money to other relatives and friends who are (or should be) more than capable of coming up with their own fundage.
My sister insists that they are better off than I think, but I fear that when they are elderly or pass away, sis and I will have to deal with a lot of their financial messes.

Guest's picture

Wow, rarely do I see evidence of "idiot compassion" as a way of life. I'd ask...what is he thinking, but he obviously isn't thinking anything, he is just doing and probably from some emotional trigger or deep seated insecurity.

Guest's picture

You didn't mention this "generous" person's nationality. It sounds like every Greek man I ever knew!

Guest's picture

Obviously people pay for a myriad of reasons, I generally try to pay when I can when out with family I have a better paying job, i will let them pay sometimes because I know it makes them feel good but I try to foot the bill as often as I can manage without it being obvious that I try and figure out which meal out is going to be the most expensive and make THAT the cheque i fight for. When out with friends we generally split, I don't like letting other people pay for me because of the tipping issue. I am a pretty good tipper, and I want the service staff (hostess/waiters/kitchen/buss staff etc) to know that they are appreciated. And while It is customary to tip in canada apparently some of us don't follow our own customs.