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Your child is hilarious, interesting, clever—frankly, he's all-around delightful. But his friends are ...well, we're all adults here, so let's just come out with it: Some of them are weird. You don't get them, and you suspect that the other grade school students don't either. You want to deal with the situation in the most unobtrusive and sensitive manner possible, and you definitely don't want to hurt anyone's feelings, but you don't want to ignore warning signs of an unhealthy and possibly toxic relationship either.

To find out how to manage this parenting dilemma, we called Matthew Goldfine, PhD, a clinical child psychologist at the Columbia University Clinic for Anxiety and Related Disorders. He treats children, teens and adults. We asked him for advice on five types of friends.

1. The (Potentially) Bad Influence

How you'd describe them: They act out, make the kinds of poor choices that you're always cautioning your children about, and are often reprimanded by the teacher.
How your child would describe them: "FUN!"

How you should handle this situation: Goldfine says this is the type of friendship that tends to worry parents the most—with good reason. "Studies show that delinquency can be almost contagious," he says. Your task is to figure out what kind of troublemaker this one is. There's no magic trick to help you with this, but you can start with the list of behaviors that are unacceptable to you and your spouse, and if you hear that this new friend is engaging in them—and worse, egging on your kid—then you shouldn't feel bad about breaking up the friendship ASAP. Goldfine says that other warning signs are "clear intentions that this child wants to make other people angry, unhappy or hurt through their actions." Be on the lookout for a child who often responds to a teacher's instructions by shouting, "NO! And you can't make me!" There's a difference between a mean-spirited kid snapping rules in half and posing direct challenges to authority, and a rambunctious or energetic one bending the rules a little.

If you just aren't sure whether this kid is a bad influence, Goldfine strongly advises talking to the other child's parents. Hold off on judging their disciplinary techniques and, instead, fill them in on the kinds of things the kids do when they're at your house. Most likely, they'll reciprocate, which will give you another perspective. If not, you'll get a sense of how involved the parents are. Assume that the parents are as well-meaning as you are and make an effort to build a relationship with them. Be sensitive to the fact that any discussion of either kids' behavior holds such dramatic potential that it was the subject of a Broadway play (the movie version of God of Carnage, with Kate Winslet and Jodie Foster, comes out this fall).

Barring dangerous behavior, Goldfine thinks it's okay to let your (ostensibly good) kid pal around with the class clown or the goofy troublemaker. Worried about how they'll grow into those teen years together? "Just because they're hanging out now doesn't mean they'll be best friends forever," he says.

2. The Unhygienic Kid

How you'd describe them: Remember Pig-Pen, Charlie Brown's filthy friend?
How your child would describe them: "His mom never makes him take a bath."

How you should handle this situation: "These are often the cases where I think it's helpful for parents to supervise and monitor, but maybe not intervene," says Goldfine. Your child is clearly overlooking this other child's flaws. Good for them! Goldfine suggests waiting until the child comes to you and asks why her friend smells funny or wears stained clothes, or talks to you about how the other kids treat him. "This could be a good opportunity to talk about the importance of good hygiene, of wearing clean clothes and of taking care of one's self." He adds that kids are more socially aware than we give them credit for, even if it might take them longer to figure things out.

As long as this child is not in danger, or putting your child's health and safety in jeopardy, step back and let the friendship run its course. He reminds us that the best behavioral models children have are their parents. "What kind of message do you want them to get from you? It's probably something like, 'As long as this person is nice to me and fun to be around, then I don't care about what other kids say.'"

3. The Obsessive

How you'd describe them: They get hung up on things, like insects, or sentient life on Mars, or opening and closing drawers over and over and over...
How your child would describe them: "They have cool toys."

How you should handle the situation: Goldfine says he often hears parents try to diagnose other people's children with psychological or developmental disorders like obsessive-compulsive behavior, autism or Asperger's syndrome. Granted, he practices in Manhattan, where every third person on the subway is either a therapist or on their way to an appointment with one. But this unhelpful habit extends far beyond the city limits. "These are heavy words, and even trained professionals are very careful with how they use them," he says. And what if this is a case of true Asperger's or OCD? "It's not contagious, and there's absolutely no harm to your child in hanging out with another kid who has one of these psychological diagnoses," says Goldfine. "In fact, it's good for them to have a variety of different kinds of friendships."

Goldfine reminds us to be aware of the impression that we're giving our kids when we criticize their friends—they really pick up on those signals. When deciding how to deal with a child whose creepy behavior bothers you more than it does your daughter or son, recall Mad Men and how Betty Draper dealt with her daughter Sally's friendship with the creepy neighborhood boy, Glen. Betty forbade Sally from hanging out with Glen, which only made Sally more eager to spend time with him. Even worse, Betty's actions made her look like an insensitive mom, pushing Sally further away.

4. The Hanger-On

How you'd describe them: She can't get enough of your daughter.
How your child would describe them: "She calls me her sister."

How you should handle the situation: Congratulations! Your kid is popular. Grade school children tend to lack subtlety in their social interactions, so this clingy behavior is likely a sign that your child is the kind of person that others are drawn to. "In this case, I'd advise following your child's lead," says Goldfine. If she seems to enjoy the other kid's company (however shadowlike it may seem to you), then let them be. But if your child says that she wants to spend time with other kids, or is giving off frustrated cues by treating this friend poorly, start a conversation with her about other people's feelings. "You could ask, 'What's a nice way to tell someone that you want to have a playdate with someone else?'" says Goldfine. "Or you could talk about strategies: 'Let's hang out with this friend these days and other friends on those days.'" Consider this an opportunity to create a compassionate queen bee.

5. That Little You-Know-What

How you'd describe them: They spilled the beans about the tooth fairy and the birds and the bees, and now they're teaching your kid dirty words—in German.
How your child would describe them: "He knows a lot of stuff."

How you should handle the situation: This kid is a parent's stealth enemy because he often appears out of nowhere to steal your child's innocence. One night you're leaving the closet light on for a na├»ve 9-year-old, and the next he's talking like a pervy European bartender. It won't be long before he'll start begging you to let him watch Superbad—and you get the sense he and his new friend already sneaked a peek.

Goldfine says that this is another situation where it's important to communicate with the other child's parents. Let them know what the duo has been up to and get a sense of how they feel about it. As with the (Potentially) Bad Influence, look for clear warning signs (cruel intentions, bullying) and draw the line at the behaviors that you deem off-limits.

If this child's annoying behavior doesn't extend far beyond dismantling beloved childhood myths, Goldfine suggests taking control of the situation. After overhearing him use curse words, explain what they are and why we don't use them. Recognize that you might have to push up the "sex talk" by a year or so. "This may not have been your plan," he says, "but it's your chance to get in on the ground floor and correct any misconceptions about what your child has been told." It's also your chance to have a bigger influence over your child than this kid has. It will be very hard to keep your child away from a spoilsport, as that will only stoke further curiosity. Besides, the cat's already out of the bag—and meowing around the playground. It's unlikely that your child is the only one who has heard this kid's R-rated stories.

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