My teenage son is stealing money from me, and he took about $100.00 from his sister's wallet, too. What should I do ?

There's some good advice in this thread. Here's more.

Behavior like this in adolescents needs to be seen as a cry for help and attention, and responded to accordingly. Their brains aren't fully formed yet, specifically the areas that apply to impulse control and consideration of future consequences.

It's not that they're not ABLE to, but that those areas don't fire automatically and can be drowned out by magical thinking and "burned-in" thought patterns left over from childhood. They need help learning how to think and establishing the neural pathways that they'll use as adults.

This is HIS problem, not yours. MAKE HIM OWN IT AND OWN THE SOLUTION. You're there to help and advise, but drop it in his lap and ask him how he plans to fix it.

If the solution is imposed through the use of parental or other authority, no learning will occur other than how to be more devious next time.

The trick here is to keep clear on the fact that even though you disapprove of what he's done, you're still on the same side. You want what's best for him and you want to help him figure out what's best for himself.

He needs to see that his behavior is wrong, hurts others, and hurts his own idea of himself, thus causing him to punish himself by acting out in this and other ways.

He needs to understand that this is a step down a path that can turn him into someone he doesn't want to become. That you love him and want to help him learn how to make better choices.

Talk to him. Find out why he needed the money. Don't be confrontational, just concerned. Calmly express how it makes you feel and ask him to collaborate with you in framing a solution. You may be surprised.

Of course, some disciplinary action is necessary, but it would be best if he had a hand in framing the discipline. Either by suggesting it himself or agreeing to it and explaining to you WHY he agrees. Re-payment should be required, but the method is up for negotiation and should include some positive experience that aids the lesson.

Punishment is NOT discipline. Real discipline is self-discipline. The point is to help him find it within himself.

If his father is around and not a total idiot, make sure you show him this advice and discuss it with him in advance of confronting your son, and get him to agree to a shared approach. Also agree to allowing either of you to be silenced by the other on a signal, to prevent your son from pushing someone's buttons and derailing the conversation. Help each other stay focused on the desired outcome, which is to curb the negative behavior.

If the whole thing goes off the rails and/or you discover that your son has a hard drug problem or is being bullied or taken advantage of or some other issue outside of the theft itself - unless your son is in immediate danger - stop in your tracks and seek professional help or a support group before doing anything further.

Youve got to address it with him and then inflict some kind off punishment.
You have to sit him down and say > taking things that do not belong to you
is no right. You have to be clear that you know he took the money and that it
is not right and then you need to inflict punishment for that behaivor.
I would maybe think about making him work to pay the money back.
that will teach him the value of things. I would find something for him
to do > manual labor that he needs to do for a couple weeks to pay the money
back. Maybe you can make him clean the house, clean the car, mow the lawn or whatever you can find for him to do and make him do enough of that to pay off the 100 dollars. I also after he works off the money > make him write a letter of apology. I also would remind him that stealing is against the law and that
he could go to jail for it. You might even want to have a police officer talk
to him and put a scare into him. Like a little scared straight episode.
You know. Like remind him that there are people who are in jail for stealing
and that being is jail is no picnic.

You have lots of responses here, and I didn't read through them.

But in a nutshell:

Any misbehavior needs a consequence. Your son will soon be 18 - an adult.
He's stealing. He needs a consequence for his actions, the least of which should be paying back any money he has already spent. If that means getting a job then, so be it.

You hate confrontation. Sorry, but for the sake of your son's future, this has to be confronted in a big way. He's stealing from his family! He's too old for this. This is not a harmless mistake. Without a consequence, this behavior gets "rewarded", and he'll probably keep stealing. He'll soon be an adult who cheats to get what he wants, and will possibly end up with police and legal problems.

It's your responsibility to take control here. Find an appropriate consequence such as paying it all back, taking away the car for 6 months, something big, and you MUST
stick with it.

Seeking advice from school guidance counselor, or other sources is necessary for the drug issue. Addiction may be right around the corner for him, and that addiction can cost him his health, let alone his life. Someone who is trained in the field can help nip this in the bud as quickly as possible.

I urge you to get some good people on your side, and be very firm and proactive, before it's too late.

Stealing, much like lying, are just symptoms of something that he's hiding or apparrently he's ashamed of...without all or more facts about his circumstances, all we can do at this point is to speculate "why" he is doing this...[like hard times, no job, living conditions, drugs, girl problems, bullying, klepto-isms, peer pressure, etc,...] ...how to deal with this concern is directly related to these prior conditions...we all know it is wrong!...wrong is wrong and needs to be addressed as such---he probably knows for sure this is wrong---He's BUSTED---now ..one way or another...kick his ***!!! [that was no help...] :(

1. Does he know that you know?

If yes, talk to him about what he needed the money for. Ask him if he feels he needs a bigger allowance. Help him find a job. And of course, find a punishment that is suitable for the crime...aka making him earn that money he took by washing his sister's car every weekend for a month or take away his social life for two weeks and put him on restrictions.

If no, give him the chance to fess up to it by telling him that his sister's missing money. Ask him if any of his friends would do that sort of thing. If he confesses, take the steps above. If he doesn't confess, I'd set him up to do it again and then the punishments would be harsher.

The main focus for me would be to find out why he needs so much money and also why my daughter has $100 in her wallet. She needs a savings account. I'd also make a point not to have cash in my own wallet and also lock my purse in my bedroom.

It's important for you to remove the temptation for him.
Lock your purses/wallets away securely on entering, (I know it sounds mad in your own home), let him know you are doing this.
I had to do this with my daughter, it worked for me, hope it helps :)

Tie him to a horse ,smack its arse then laugh at him as he gets dragged down the street

A hundred dollars?! FIRST IS FIRST ask him what he did with that money, (make sure he is buying anything he shouldn't be). Also you have to communicate with him more, figure out why he couldn't just go to you directly. Lastly make him get a job so he can pay you back, don't go soft on him. What he is doing is a cry for attention, give him it or his behavior may escalate.

I did that as a young teen. I hate remembering it now. Being humiliated and accused by my mother worked to stop it immediately.

I used to take small amounts of change from my parents and brother when I was younger. Somehow I grew closer to my family and realized that they where there to help me with whatever I want, Money is not what I want... I feel like scum looking back at it and now it seems I am the one giving and avoid taking anything from anyone. thievery is dirty and somehow you need to get this across to him.