My 16-year-old's friend is shoplifting - should I say something?

My son mentioned a shoplifting incident that happened recently with his friend I'll call "Sam".  This is a friend he was close to when they were younger, but now they only see each other a few times a year. Sam and my son were with a group of friends, and they stopped at a convenience store for treats. My son told me he saw Sam put a bag of candy in his pocket that he didn't pay for and later offered to the group. My son seemed sort of baffled, like he was asking me what he should think about this. We talked about stealing and what he might have said when the candy was offered. He asked me not to say anything about the incident to Sam or to Sam's mom.  

Now I'm thinking that someone needs to clue Sam in about the shoplifting. I don't think his mom will do it, so maybe I should. I had a sister who stole things at his age. Our parents weren't paying attention, and it got worse as she got older, and caused a lot of problems. Sam doesn't have anybody either who will tell him he's done the wrong thing. He's always been kind of a sneaky kid, but his mom makes excuses for him and is sort of in denial. Once he broke an antique wall sconce at my house. The kids were playing, it was not intentional, but I was home at the time and he didn't tell me about it, and when I saw what had happened, he denied responsibility. I decided I should tell his mom, NOT because I wanted her to pay for the damage but because I would want to know if my kid broke something that was important to someone else, and then didn't apologize or take responsibility. I'd known them a few years, so I felt comfortable calling. She thanked me for calling but then told me that Sam is very sensitive and has a hard time dealing with criticism, so she didn't feel she could bring this up with him right now.  So after that, I didn't tell her about Sam's misbehaviors. I don't think she would take any action this time either.

So ... if you were me, would you wait until an opportune moment and have a private chat with Sam? Or would you call his mom?  Or would you just keep your mouth shut and mind your own business?

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I would bring the subject up again with your son, and tell him 1) you are concerned that Sam's misbehavior is going to escalate and your son will be caught up even more in it, and 2) request your son's permission to share his observation of the shoplifting incident (which was in fact a crime) with Sam's mom. If you can have an open discussion with your son about both those things, regardless of if he agrees that you can share it or not, you should feel reassured about your son knowing right from wrong, which is the bottom line here. Sam obviously sounds like a challenging kid and if your son was younger, you'd simply refuse to let them associate, but obviously a 16 year old can pick his own friends so you simply have to trust your child to choose wisely. You didn't observe the shoplifting yourself, so that's another reason to let your son "guide" you on that too.

I am very glad you had the wisdom of considering 'minding your own business' as an option.  You do not know this family's circumstances and they do not need to fill you in on them.  I'm sad 'Sam''s mom had to explain things private to you.  On the same note, we all think we know better and our values are the best.  Values are subjective.  I suggest you have compassion for the kid and the mom and leave them alone.

If your son doesn't want you to say anything you should leave it alone although you should have a talk him about whether or not he wants to continue having Sam be apart of his life.

Come on. You have tried with this mom before, she doesn't care or can't make herself confront it, you're not going to suddenly get thru to her this time. Just encourage your son to keep distance from this walking disaster, which it sounds like he isn't interested in him anyway, and keep your own distance. The mom sounds like an absolute idiot. Telling her is NOT going to save this kid. 

Of course you should tell his mom that you suspect he is stealing. However-- your tone seems very judgey-lucky you for having a well behaved child but believe me there are plenty of parents out here who do our best to raise law abiding and morally correct children - yet still they push the limits. I invite you to channel some compassion prior to your outreach.

I disagree with another parents description of not saying anything as a sign of "compassion" .

Not saying anything is a sign of weakness and cowardice.

My daughter was friendly with a girl who was shoplifting ... at age 8!! I immediately told her her mother- as kindly as I could. She was grateful that I had the guts to talk about a difficult subject and immediately set her own kid straight. 

Shoplifting is a serious problem. It can lead to arrests and getting a criminal record which can complicate a young persons chances for future success. 

Telling a parent the the truth is the biggest the gift you can give this family. It's not easy- but it's the right thing to do!