My kid’s friend is a criminal.

Last week my six year old lost a tooth and the tooth fairy left him five dollars in singles.  (I know, times are tough all over.)  My son left the money on his bedside table, as he is planning to buy something next time we go to Target.  A few days later his buddy came over to play.  As I was passing the bedroom I saw the friend holding the money.  He asked me how much money was there.  I told him “five dollars” and kept on going.  The next day as I was in making my son’s bed, I saw the money and upon counting it, noticed that a dollar was gone.

Admittedly I didn’t ransack the room looking for a dollar bill, but I have a sneaking suspicion that the friend may have “accidentally” put it in his pocket. What shall I do?  I know the parents well and also have been told in confidence from his mother that he has sticky fingers.

I know its only a dollar, but do I let it go and allow this boy to end up in juvie for shoplifting or shall I cause drama and let the parents know of my suspicions?

I think you should invite the boy over to your house again. Tell him there’s a pony and some cake in the back room, but actually make it pitch black in there except for a super bright spotlight shining on a small metal chair. Make him sit there and watch you stick pins into pictures of his mommy and the Easter Bunny until he starts crying and confesses.

You sound like a nice person, though, so perhaps instead you should just look around for the dollar bill. Be really thorough, and check with your son to make sure he didn’t lose it or do something with it. Then think about your motives. Would you tell the friend’s mom because you secretly think the kid is a little shit and you want him to get in trouble? Would you tell her because you’re friends and you know she’s worried about her kid’s kleptomania? Would you want to know if your son stole a dollar from her son?

It’s tricky talking to another mom about when her kid misbehaves. Once I was at the park and another mom was like, “EXCUSE ME, YOUR BOYS ARE KICKING EACH OTHER AND TRYING TO PUSH EACH OTHER DOWN THE STAIRS,” and then when I was like, “Oh, I know, I saw them,” she gave me a hairy eyeball and said, “Well, I could never watch my children hurt each other like that.” I now despise that woman for all eternity. She wasn’t minding her own business.

This, however, directly involves you and your son, and I think since you know the other parents well and she has confided in you about this issue already, you can say, “Sally, this isn’t a big deal and I don’t want you to think I’m angry or upset at all, but I’m pretty sure Bobby stole a dollar from Jimmy’s room. Jimmy doesn’t even know it’s missing, and I don’t want you to do anything about it for my sake; I just remember you telling me you were working on it with Bobby and I thought you might want to know.” If you can say this without a touch of self-righteousness, go for it.

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