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My son is a 13-year-old honor roll student. He comes home and has all his chores done by the time I get home. He is a great kid.

He was hanging out with his friends; this group has been friends since first grade. They were at the local skating park, and saw a donation box for clothes and shoes, saying 'single shoes accepted'. For whatever reason one of his friends (a girl) asked him to donate his right shoe, and he did.

After they got home they where laughing about it and decided to donate all his right shoes, worth about $575, including one from a $145 pair he had never worn and that he had gotten only the day before.

I found out the next morning when he came downstairs, wearing a pair of shorts and a t-shirt, his left shoe and a sock on his right foot. He told me he donated all his right shoes to charity. He left wearing a sock on his right foot.

When he got home in the afternoon I asked him where all his right shoes were and he just laughed it off and told me what happened. When I tried to talk to him about it, his attitude was "it’s no big deal". I asked why he did that and he said it was funny. It doesn’t bother him a bit that he doesn’t have but left shoes. He thinks it’s funny and apparently has no concept of the amount of money he wasted. I hadn't budgeted to replace shoes until next school year.

How should I handle this?

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    Are you all so detached from your childhood that you can't see he did it for the girl? You don't need to teach him that donating things are wrong, you need to teach him that silly impulsive acts might be funny in the short term, but wasteful in the long term and unlikely to help him get a girlfriend anyway. Who knows, maybe you'll save money when he learns a lesson here rather than doing something similar 4 years later with his first car. Don't overthink it, but do recognise the absolute core, as you've implied, is that he wants a girlfriend.
    – Dom
    Commented May 23, 2015 at 15:53
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    He got the girlfriend
    – luann
    Commented May 23, 2015 at 16:03
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    this is so not about the money or the shoes, it is about the girl
    – user6497
    Commented May 23, 2015 at 20:47
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    Noone is focusing on the correct question here: Why does the donation box accept single shoes? Now there's going to be a bunch of people running around with the same size shoe as your son, @luann, with only a right shoe.
    – jwir3
    Commented May 26, 2015 at 20:13
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    Stick with the plan, and don't replace his shoes until next season.
    – Jon Watte
    Commented May 28, 2015 at 3:49

15 Answers 15

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  1. Donate the left shoes in the same donation box. Whether or not they are able to get single shoes to those who need them, having a half-pair sit in your son's closet does nobody any good. Might as well finish what he started.

    By only giving right shoes, he has potentially wasted the charity's time: many people need only one shoe, but there's a chance this particular charity doesn't serve that need. (Thrift stores, for example, typically sell whole pairs. Whether they would re-donate single shoes depends on the charity.) Take the opportunity to teach him about why shoe donations are needed, who will benefit from those shoes, and so on.

  2. Buy one pair of shoes from the organization that runs the donation box. If you can't figure that out, or there isn't one near you, any thrift store will do!

    He does need to have shoes, but they don't have to be fancy and they definitely don't have to be expensive.

  3. Optional. Have him work off the cost of future new shoes in chores and odd jobs around the house. You set the rate, he does the work.

    Ultimately, your goal should be to help teach the value of things he owns. A parent goes to work to get a paycheck, which eventually becomes shoes, food, housing, and so on. Having that be discarded (even in a "positive" way like donating to charity) is understandably hurtful as a parent: not only is the physical object being undervalued, but your effort and care in providing for him was not acknowledged and considered. ("That was $600 of shoes. That's a lot of full-time work for me/other-parent, just to pay for shoes. I'm hurt you think that's so worthless.") Having him put in some work to get the next few pairs of nicer shoes is going to help drive that point home.

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    3. is tricky - it's basically a monopsony, you're the sole provider of work, so you can set the rules. The only way this can work is if you're not the only provider - is it possible for the kid to do work on his own, or is it against the child labor rules etc.? Are there available jobs he can do at his age? Etc. If you end up being the only provider of money, just think about how you'd feel if the roles were reversed - forced to pay by working at someone else's whim, with no choice of your own and no options to choose from.
    – Luaan
    Commented May 25, 2015 at 7:50
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    You being the only source of money makes this easier, not harder. It's not your fault he put himself in a situation where he can be exploited. He's just lucky the only person who can do the exploiting loves him unconditionally. Can't say the same for most business owners/managers.
    – corsiKa
    Commented May 25, 2015 at 15:07
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    It is possible to give him a choice - do the work, or make do with one pair of cheap shoes. Commented May 26, 2015 at 9:43
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    +1 for 1) alone. The damage on your end is done (unless you can get the shoes back from the charity), so at least do some good on the other.
    – DevSolar
    Commented May 26, 2015 at 15:15
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    For 1, the decision to donate the left shoes really should be his - preferably after he realizes that a box of right shoes is barely any more useful to the charity than his closet full of left shoes is to him. I think taking that decision away from him would tend to reduce the learning potential of the entire sequence of events.
    – brhans
    Commented May 28, 2015 at 14:54
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Hehe, that is pretty funny.

Eh, don't worry about it. Kids do silly things, this isn't one that's going to get him killed. Sometimes people just need to do something that goes against the normal course of action, ya' know? It'll be a funny story he can think about/tell other people when he's older.

After he's had his fun, and then gets tired of walking around with only one shoe, you can have him pay the cost when he's ready for another pair. Just wait, he'll come around and start asking for new shoes eventually. Then say, "Sure, how much of your allowance are you willing to spend?"

Maybe get him a $2 pair of flip flops in the meantime if you're worried about him stepping on a nail or something.

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    @Zibbobz I think that Guest's point is that sometimes the natural consequences are enough, and you don't have to impose more consequences. Commented May 22, 2015 at 3:22
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    @Zibbobz I feel that the natural consequences will make it obvious that it was wasteful. You let that kid walk with one shoe for a few days and he's gonna regret and realize his mistake on his own. And if he wants to get a new pair of shoes, he will have to admit that there is a problem. I feel that realizing your mistakes on your very own is far more gratifying that having someone else tell you.
    – Saturn
    Commented May 22, 2015 at 14:26
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    Agree with @200_success. Teenagers have cotton in their ears, and experience is the best teacher. The kid sounds laid-back, so he may go days or weeks without shoes just fine, but at some point, he's going to want some. Let him buy them himself. Also, let him pay for his own shoes for up to a year in the future. If he asks why, calmly say, "I bought you nice shoes before (including some very expensive ones), and you gave them away as a joke. When I asked why, you laughed and didn't apologize. That hurt my feelings, and made me feel like you don't appreciate the things I buy for you." Commented May 22, 2015 at 15:11
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    This is the best answer. Part of your problem was that your kid had $500 worth of shoes that he didn't have to work for and doesn't wear. He's reaching an age where he realizes that your pockets are (effectively) bottomless, and assuming that material goods have no value. If you ground him or make him work it off, you're inserting yourself as the mediator between his actions and reality, which makes you the bad guy, and doesn't address the point. Let him live like he has limited income for a while and it will put things in perspective.
    – Shep
    Commented May 22, 2015 at 18:24
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    +1 him walking around thrift shops looking for $5 shoes in his size with his allowance seems like a great opportunity to learn the value of things and that actions have consequences. Since he got the girl, you can't stop him thinking "Totally worth it" (and to be fair, it's a great story, you will laugh about it when he's older) - but you can at least make him understand what it means to save up for essentials. Maybe also make him phone the charity to ask if they want the left shoes too, for the civic responsibility angle. Commented May 25, 2015 at 22:31
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First off, I strongly recommend taking the money out of your thinking. Teenagers can do foolish things that can be expensive, but it just doesn't help to dwell on the cost of the shoes. Remember: your son is worth a lot more to you than those shoes. Presumably it will be possible to speak with someone at the donation center to get those shoes back.

Second, I'd consider the possibility that your son isn't nearly as blithe about the situation as you suppose. People often cover up feelings of shame and regret by making out that what they did was "no big deal". It's not your job to make your son feel anything. Your job as a parent is to help your child become an independent and productive adult. So it doesn't matter whether your son feels foolish as long as he learns to avoid being foolish in the future.

Third, it's really important to listen to and understand his reasons for giving away the shoes. If he says it was just to be funny, take that at face value. You'll need to talk out how he might act on the desire to do something funny without doing something he might regret or that might cause you pain. Be sure to encourage him developing his abilities and talents. Once you've made that clear then talk about how this particular event hurt you.

Finally, consider an appropriate consequence for his behavior. Going without one shoe is the natural consequence, but perhaps too harsh for a simple mistake of youth. If he has an allowance, consider requiring him to pay half the cost of replacing his shoes. If he doesn't have an allowance, consider having him do roughly the equivalent hours of chores he'd need to do if you paid him a wage. The cost currently falls on you, but when he leaves the house, it would have been his responsibility. The time to learn that is now, when the consequences are relatively minor.

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    A long conversation about the consequences that have arisen from the "joke" (including the long conversation as one of the consequences) can be pretty useful.
    – Acire
    Commented May 21, 2015 at 0:17
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    A good response. I agree that going with one shoe would be a natural consequence. However, I think it would be seen as a sign of neglect by outside observers, rather than an acceptable consequence.
    – user11394
    Commented May 21, 2015 at 0:28
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    +1 for your second paragraph. This is something I sometimes forget with my own children.
    – WoJ
    Commented May 21, 2015 at 9:00
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    Presumably it will be possible to speak with someone at the donation center to get those shoes back. Perhaps the parent could sort out some kind of trade swapping left for right so that the child gets some shoes he can wear and the charity gets pairs of shoes where previously they only had right shoes. Commented May 22, 2015 at 17:04
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    +1 for overall strong answer, but I strongly disagree with "First off, I strongly recommend taking the money out of your thinking". 13 is old enough to understand the value of money (in overall human development picture, even if not in pampered First World 21st century coddled youth environment) - people used to work for a living at 13. If you don't teach a child the value of money at 13, you're at risk of ending up with a wastrel when he's 23 and 33.
    – user3143
    Commented May 23, 2015 at 14:38
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Consider items you give to your child a gift to them. The money spent on it then becomes irrelevant since it isn't yours to use; it's theirs. This makes dealing with kids breaking things much easier as it becomes their own responsibility and you'll feel less reason to keep replacing things they break. They learn value much more quickly that way.

If he gives away all his shoes, just give him a single, second-hand pair you buy for cheap that he can wear from now on. You'll probably teach him the cost of these jokes and he can draw whatever conclusions he wants from what happens when you give your stuff away. He might even thinks it's worth it; that's a perfectly fine outcome.

If an afternoon of fun is worth having to walk on second-hand shoes for a few months, than clearly all the money you spent on the shoes was wasted on him anyway. Consider it a valuable lesson for yourself that apparently your kid isn't very interested in expensive shoes. There's probably lots of other stuff you can spend that money on that he or you will appreciate a lot more.

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    I agree. Financially, the relevant sum is what the parent will have to pay to replace the shoes, not what they cost in the first place. Commented May 22, 2015 at 17:08
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    +1 "If an afternoon of fun is worth having to walk on second-hand shoes for a few months, than clearly all the money you spent on the shoes was wasted on him anyway."
    – Geobits
    Commented May 22, 2015 at 17:50
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    I don't really agree with the first paragraph (kids need to understand the value of money even before they have to earn it themselves - precisely so that they'll know how to manage it when they do need to start doing so,) but I do agree with the last paragraph. Unless the kid specifically asked for the $145 shoes, it sounds like he doesn't care much about expensive shoes.
    – reirab
    Commented May 24, 2015 at 7:52
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    @reirab I agree that kids need to learn the value of money, but receiving things from your parents and not being allowed to have full responsibility over them doesn't really teach anything. By treating the items as his and not denying this behaviour (by not giving him new ones) you let him learn the value of a pair of shoes. If you just scold him and buy him more, he won't learn a thing.
    – Erik
    Commented May 24, 2015 at 14:17
  • I disagree with parts of this answer due to health reasons. Wearing poor shoes for months is not good for the feet. Short term it is just uncomfortable, long term it may go as far as damage the bone structure. In particular in a child!
    – mafu
    Commented May 24, 2015 at 14:59
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I would be more concerned that he thought it was funny to make fun of the disadvantaged. Donate the left shoes to the charity.

Then buy him a cheap pair of shoes, if he wants expensive fancy shoes he can save up for them so he will learn the value of shoes and will respect gifts from you.

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    The charity itself said they accept single shoes. There are lots of cases where a single shoe is appropriate -- like surgery or injury makes only one shoe necessary (or one shoe is cut open and modified such that one may not want to destroy a matched pair), or a person's feet are not the same size such that they are willing to wear a pair of similar, though not exact matching shoes. So while donating both shoes may be preferable, the charity itself said that they have a use for mismatched shoes.
    – Johnny
    Commented May 21, 2015 at 21:43
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    Agreed. This would be of far more serious concern to me than the money. In the end, you'd have to know the kid to discern his actions, but I would certainly want to get to the bottom of "Why?"
    – Wyrmwood
    Commented May 22, 2015 at 2:03
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    @Wyrmwood 'Why' seems pretty obvious in this case. A girl asked him to do it. A girl that he apparently liked (since the comments on the question indicate she's now his girlfriend.) Guys, especially young guys, frequently do stupid stuff to impress girls (especially young girls, who, for some reason, seem to be impressed by stupid stuff.)
    – reirab
    Commented May 24, 2015 at 7:56
  • Single shoes will most likely end up being reycled, at minimum value for the charity.
    – gnasher729
    Commented May 24, 2015 at 21:52
  • I made a comment to this affect on the question, but it was deleted by either the asker or flags. Your answer hasn't been downvoted into non-existance, so I can only assume it was the asker deleting a comment that was somewhat critical of their son. Upvote for you, anyway.
    – iabw
    Commented May 28, 2015 at 12:40
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With care you can reverse this situation, turn it into a teachable moment, and gain massive respect into the bargain.

Recognise that 13 year old boys do really dumb things for girls

Really stupid, falling over themselves in circles like a little puppy dog dumb.

At that age, swapping a shoe for a smile from a pretty girl might seem like a good trade. Attraction clouds judgement, and he presumably hasn't learned to handle himself yet. This is something you will need to teach.

Make him aware of the problem he has caused

If he's a good kid you can explain to him clearly and calmly the family financial problem he has caused. Show him the budget spreadsheet and the hole he's made. Show him what will have to be sacrificed to make up the difference and how that's going to hurt everyone.

Be calm about it and not accusatory. He will probably come to understand the problem he has caused.

Give him natural consequences (but not too severe)

Making him walk around with only one shoe is probably a bit cruel. I would buy him a cheap pair of shoes and make him use those for a little while.

Remember it's only shoes

It could be a lot worse. He might have started smoking or taking drugs, or dropped out of school. Shoes can be fixed. Maintain perspective.

Gain respect by quietly solving the problem

At this point you have two options, you can either hold him to account for the money, or you can forgive, move on, and try to fix the problem.

If you hold him to account, your son goes in debt to you to the tune of $500. This is a big deal. It's a true statement that the borrower is slave to the lender, I don't think this is the relationship you want with your child.

My advice would be to call the number on the charity box and explain what happened. You might be able to get them to open the box and recover the shoes.

Make him sweat for a while until he shows contrition and learns the lesson, then replace the shoes in his wardrobe. Your son will be impressed. You'll earn his respect for cleverly solving the problem and strengthen your bond with him. If he respects you he will care what you say and think.

You will also solve a financial problem. All his money ultimately comes from you after all.

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    The question even put an emphasis on the fact that the boy did this because a girl told him to, and this the only answer that mentions it. This may signal that the boy in question may have an unhealthy obsession with getting a girlfriend. I was like that at his age, I would have done the same if a girl asked me to. Now I'm in therapy for being obsessed with girls after years of unhappiness. I wish it was addressed sooner. Maybe it's worth a visit at a psychologist, it may spare him a lot of pain.
    – matega
    Commented May 23, 2015 at 13:13
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    You're not teaching responsibility if you fix his mistakes. That's going in the opposite way...
    – msb
    Commented May 24, 2015 at 11:43
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    I was going to upvote until I hit the spot about fixing it. The kid would be considered a full fledged adult in some cultures. At 13 it's no longer appropriate to fix problems for them. (Unless they're very serious problems.)
    – RubberDuck
    Commented May 24, 2015 at 16:47
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    @RubberDuck - I agree with you. My father always used to say "never a lender or a borrower be". He refused to lend me money when I was in trouble, but would freely give of what he had. This did not teach fiscal irresponsibility, but the opposite as I saw how money could be used as a tool. A lesson can be learned in an hour, in a moment. I don't think it's necessary to drag the problem out until the debt is paid, it only needs to be dragged out until the lesson is learned. Just my opinion. Commented May 26, 2015 at 11:27
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    @matega The fact that he did something because one particular girl that he liked told him to (further, from the way the question is worded, it sounds like it wasn't just her and all his friends thought it was hilarious) does not necessarily mean that he's "obsessed" with getting a girlfriend in general. Commented May 27, 2015 at 9:37
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Make the charity whole

Donate the left shoes as well, that way the charity is made whole.

Why did they really do it

It's possible they found it funny b/c of some teens' snark sense of humor to have the charity looking for matching shoes, only not to find them, as a previous answer has said. As a parent, it's hard to know if that was the root of the humor, but if he and his friends truly wanted to help a charity that wasn't the best way to go about it.

No shirt no shoes no service

Obviously your son can't walk around w/out shoes everywhere, so you really don't have a choice but to buy him a new pair of shoes. I would give him a small amount of $ to buy a new pair of shoes, with the caveat that he understands what he did wasn't the wisest choice.

Let this be a lesson

As others have said, I would reserve the discipline for later, first mistake and all, and nobody got hurt (other than dad's wallet of course).

Leadership skills

Lastly, I would encourage you to pay close attention to the choices he makes at the influence of his friends. I'm not implying you don't pay attention to your son, but what I am saying is: find out if he is more of a follower and less of a leader. For example did the others donate half of a pair of shoes as well? Or did they just talk him into it?

This is worth looking into, because a one off incident that he and his friends did together (albeit unwise) is different than his friends either having a pattern of, or (with this incident) establishing a precedent of, talking him into making the unwise choices, because they'll know he's likely to do it if they apply enough pressure. I have been on both sides of that coin and it was only later after mistakes I learned how to become a leader among my friends, which in reality meant making my own choices, encouraging them to make better choices, and separating myself from them when necessary. Without getting too personal, having a father around would have sped up the development of those qualities, so I encourage you as a fellow father to pass the torch!

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    Charities can use single shoes for the millions of people who only have a single leg, eg all the children maimed by cluster bombs or landmines.
    – DanBeale
    Commented May 21, 2015 at 13:49
  • @DanBeale that's a good point, I didn't think about that. The question then becomes, what will his son do with single shoes? Commented May 21, 2015 at 14:10
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    "(other than dad's wallet of course)" Did I miss something? ;-) Even if she's a SAHM, the whole family is influenced by this action. I agree, though, that if they can afford the shoes easily, the focus can be elsewhere for the moment. Commented May 21, 2015 at 20:20
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    @DanBeale: Charities can use pairs of shoes to help two children maimed by cluster bombs or landmines.
    – gnasher729
    Commented May 24, 2015 at 21:55
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    @Dronz: It wasn't a single shoe donation box. There is no single-shoe donation box anywhere in any country. They accepted single shoes. Like if one shoe out of a pair of trainers goes in the washing machine by some accident and is destroyed, you can donate the other shoe. Should a woman have the awful bad luck of losing a foot, she can donate the 100 left shoes of her hundred pairs of shoes. Otherwise, donating one shoe out of a pair instead of the whole pair is frankly idiotic.
    – gnasher729
    Commented May 30, 2015 at 12:45
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I would learn him to respect the value of money, and have him buy the next pair of shoes from his own pocket.

This way, it would only hurt his own pocket if he choose to do the same over again. (Or something likewise)

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    Sounds like the kid is smart enough to have a more adult conversation about it. I think unilateral punishment would just model immature backlash, and rightly undermine respect for the parent. Keeping the respect of teenagers is tricky enough without entering into power games with them.
    – Dronz
    Commented May 23, 2015 at 16:28
  • It is absolutely not a power game. It is as easy as showing him that doing this stuff has a consequences. Commented Aug 19, 2015 at 6:42
  • It would show that it has that kind of punitive consequence, when dealing with even someone who loves you (even a parent) when that "adult" is still partly a child, who changes the rules without agreement.
    – Dronz
    Commented Aug 24, 2015 at 18:44
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Divide 575$ by a reasonable hourly wage and make him work that many hours for charity (for free). Thereafter forget about the incident and the 575$.

This will sharpen his mind for the problems of the not so lucky, and he might consider thinking a bit more about any future actions. For yourself: be happy about the lesson learned.

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    Oh really? I can also see it sharpening his sense of irony and his disrespect for the parent's financial concerns, leading to him acting out in even more financially damaging ways.
    – Dronz
    Commented May 23, 2015 at 16:30
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How is you family dealing with ownership within the household? If the shoes were "his," free and clear, then he can do whatever he wants with him. However, if when you bought them for him, there were strings attached (like "these shoes are expensive, but we think you'll do good things with them"), then he did not have the right to give them away without consulting. I have a suspicion this is in a grey area within your household. Otherwise he either would not have donated them, or you wouldn't have had problems with him doing so.

Personally, I think learning about donations is a valuable lesson, even in such an abstract situation. Sure, it'd have been nice if he didn't donate something he currently needed, but that's a lesson one has to learn. Better he does this now than later in his high school career when he tries to donate the car you got him!

Now, all of that is generalized psychology. I feel qualified in delivering that part. The next part (what to do about it) must come with a disclaimer that, while I was a 13 year old boy once, I don't have any of my own, so take it with a grain of salt.

The conversation that probably needs to happen is one of the complexities of ownership within a household. He should know you still love him, but he also needs to know that his actions have consequences. You feel betrayed by his actions, because you feel his sense of ownership did not align with yours as a parent. Explain that there will be consequences, because now you have to consider his apparent treatment of his property when buying new things "for him."

Perhaps you don't buy him a new pair of shoes. Perhaps you buy a new pair of shoes and loan them to him like a mortgage (do you have a home or an apartment? If this happens to be an opportunity to teach him about some of the bills you have to pay, so much the better!). Work with him on the choice of shoes. They're going to have to be affordable and durable enough to keep his feet covered until he can pay them off, but they also should be a style that he can wear to school. It will likely be a tough choice for him, especially if he likes the "cool" shoes which cost a lot. You aren't obligated to loan him just any set of shoes -- only shoes which you think benefit him at the price/goodness ratio you see fit.

You might also start being more strict about use of objects you "own," but I would be careful with this approach. It could create more of a divide between you and your son. However, at least for the short term, he needs to understand that you respond to his choices (define "short term" according to how long it takes him to learn a lesson), however you choose to implement that.

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    @Court Ammon's. No they are his shoes he works for the things he has he does most of the yard work feeds the stock helps keep house He said he understands the money and didn't expect me to buy new ones he's fine like he is it's not a big deal. I guess that's what bothers me is the I don't care attitude I have never see
    – luann
    Commented May 22, 2015 at 18:35
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    @luann ahh. Your "I hadn't budgeted to replace shoes" lead me to believe that the Family bought the shoes for him, rather than him purchasing them himself. In light of that, I might blame the attitude on a mixture between him knowing that he did something big and wanting to be cool about it, and a general sense of confusion as to how it feels to give a donation (which can be disconcerting), and a desire to impress a girl. Confound those together, and I'd certainly develop a defensive attitude along the lines of "I don't care," just to give myself time to understand what just happened!
    – Cort Ammon
    Commented May 22, 2015 at 23:03
  • Most people grasp the purpose of clothing and footwear when they're very young, typically around 3 or 4. Also most children learn from a very young age that left and right shoes aren't interchangeable. Commented May 24, 2015 at 6:17
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Let him live with the consequences of his actions and walk around with one shoe. If he has a job or an allowance, he will quickly learn just how valuable a pair of shoes are after spending a few days with only one.

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    And who's paying for the socks he shreds this way and the medical treatment if he steps into something and cuts his foot? I see where you are headed ("natural consequences" is basicaly a good concept), but this might be a bit short-sighted.
    – Stephie
    Commented May 21, 2015 at 7:35
  • What's the connection between having "a job or an allowance" and "spending a few days with only one [shoe]"?
    – Acire
    Commented May 21, 2015 at 10:47
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    @Stephie: That's not really true. A few socks is worth far less than the shoes, which is just one example of the financial cost of him not understanding such matters. It would be great value for money to lose a few socks this way. As for medical treatment, presumably the OP has insurance. Ultimately, you're talking about an OP who spent $145 on a single pair of shoes for their child- not exactly struggling to feed the family here.
    – DeadMG
    Commented May 21, 2015 at 14:46
  • It's not so much about the money, but about teaching a 13 year old what is right and what is wrong to do (and perfectly legal stupid acts like this are wrong). Although making him walk in socks is a bit much IMHO, wearing used shoes from a charity shop would be better.
    – gnasher729
    Commented May 30, 2015 at 12:39
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You'll need to get replacement shoes in the cheapest possible way. In the UK, I'd go to the nearest charity shop and try to find the cheapest pair of used shoes that he can wear.

Anything else will teach the boy that he can do significant financial damage to his parents without any consequence for himself, which is not a good lesson learnt.

After some further thought: It seems the boy is working to make money, and has been paying for these shoes, and some people think because he paid for them, he can do with them what he wants. That's wrong. He is a child, and his parents' job is to prepare him for life. They have the power and the duty to do that. So even if his behaviour only hurt himself, they still have to teach him that it was wrong; a stupid destruction of value.

So my advice of going to a charity shop and buy used shoes stands. I'd also ask him to figure out what the ecological consequences of his actions are. The single shoes will go into recycling and make a tiny bit of money that way (maybe one dollar per kilo of single shoes if they are lucky), but a lot of energy, raw materials, and possibly lives of animals have been wasted. And he should figure out that donating both $145 shoes to this charity would have been much more effective in helping people.

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I understand the situation, and here some things that have helped us with our four kids:

  1. Your son needs a stern talk from Dad to correct his behavior related to girls.

  2. Buy him some cheap shoes from the local thrift store.

  3. Implement the allowance/budget strategy: he earns weekly income based on chores, finishing school-work, and attitude. Establish a reasonable budget (i.e., saving, giving, cash, clothing) where he must purchase his own shoes.

In our household, my wife and I have found that step #3 is a well-founded approach to correct our children's behavior over time...and it has instilled in them respect for us and an understanding of how money works.

Here are some helpful references for step 3:

Cheers!

2

I thought twice before posting this, but since almost all posts are about the money, another perspective may enrich the debate. I don't know which country you are from, maybe I'll touch some cultural sensibilities. Anyway, maybe it is better to read this from a complete stranger. In my country we value a lot social interactions, maybe that's why your son story shocked me. Please take a moment to think about what I have to say.

First, I believe I'll do stupid actions due to girls till the last day in my life. It is completely normal, specially if you are 13 years old.

But with 13 years, your son isn't a child any more. The girl and her/his friends were poking fun at him. From his reaction, he liked it. Other people were laughing about something he did. He made someone happy. It looks like he was craving so much for any kind of social interaction, that he tried to get a little more of it giving all his shoes.

I've known a bunch of guys that excel at school but don't have a clue in interpersonal relationships. They usually aren't very happy. Some of them didn't even became functional adults. All this story, may be a cry for help.

My advice is that you should talk to other adults and children that usually watch your son in social settings. Ask how your boy behave, if he knows how to interact. See if it is really a problem.

To be sociable is a learnable skill, and a lot easier to learn when you are young and have a lot of opportunities to interact with your peers. Your son will probably be more successful in his career if he knows how to do it. A professional, a psychologist, may help.

Money is the least important thing in this story. Your son will probably be happier having good and valued friends than being an honor student.

1

I think it is an opportunity for you to help your son understand why organisations ask for donation. You could tell him, donations are usually made to help people in need.

If you could figure out the best way he understands that, it is essential for donors to think about the people in the receiving end. If he had thought about it he would either have donated the pair because the box said "that they accept one shoe but didn't say they don't accept pair". He could have helped more people or simply he kept the pair for himself and haven't have lost any pair. By simply donating without thinking he now can't use them for himself and he could have served more people by donating pairs.

The point I am making is to stress the importance of thinking before donating.

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