9 year old can't entertain himself

[wadeandanet]

I have a 9 year old boy who can't entertain himself.  He has always been a "harder" child.  He has never been able to entertain himself.  As a matter of fact, I can remember when he was a toddler I had another baby and he would just hang on me and couldn't ever play by himself.  It made me not enjoy him very much and I wonder if it has made insecurities now.  He used to throw tantrums and run off and hide in his room rather than address the situation.  Anyways, long story short, about 2 years ago, I decided he either needed to go to therapy or I did.  The child therapist said he had oppositional defiant disorder, and I took some parenting classes to help him.  Over all, it made a huge difference.  I worked a lot on positive reinforcement and filling his cup.  However, 2 years later, he either wants screen time (iPod, computer, TV, or video games), or walks around annoying everyone (he has 2 brothers and 1 sister).  I also have found that he has a serious problem with loosing, and quits a game or ruins everyone else's game if he is loosing.  He is also known to cheat if he is loosing.  I think he is insecure, and does have some problems with depression and this is some of the problem.  Half of the time I let him play the computer just to keep him from bugging everyone else and disrupting the peace.  I don't feel good about this, and am wondering if anyone has any suggestions about cheating, and entertaining himself.  I am at a loss...

[Sandman2]

   I saw some of the symptoms of ADD (frustration,insecure, cheating.) Typically, for a smart kid they will do well until math trips them up.  Multiplication requires few steps, long division requires many.  If a child is not paying attention, their natural intelligence will not help them get through it.  But ADD does not sound like its the problem.
  However, I suspect at least part of this is dealing with his brothers and sisters.  I see he is kind of the middle child - two older, one younger?  Curious if the younger is a sister.  Anyway,  you could look for games that depend more on luck then logic to kind of even the field.  Mexican Train - a game with dominoes should do that.  And the whole family should play it together.
    The poker chip system sounds like a winner!   I think what will be interesting to see is what he chooses.  I also would work really hard at setting up a few play dates with school friends or finding some kind of sports program to get him involved in as specialmom suggested.

[wadeandanet]

Thanks for everyone's advice and comments. After hearing specialmom and marklakewood's advice, I decided to go back to what was effective that we were doing right after we saw the psychologist.  I knew if I went to the Dr he would ask how we were doing with what he'd had us do.  
One of the reasons I posted this is because we are on a track system at school and have off from Thanksgiving to New Years this year.  I was feeling concerned because I didn't want him inside video gaming for 5 weeks.  So anyways, when I went to the counselor, one of the things he had us do was to have a poker chip reward system.  He does his piano, outside time, exercise, reading, chores, brush teeth, etc, and he earns chips that he can spend on TV, video games, date with mom, dessert etc.  It acts as an immediate positive reinforcement for him, and gives him the opportunity to decide what he wants to do to earn it.  We are into it 3 days, and so far it seems to be doing really well.  I still think he needs to learn to entertain himself better, but most of the misbehavior has decreased.  

[wadeandanet]

He isn't doing division yet.  Why do you ask?  He does fairly well in school.  He gets his work done without a lot of prodding from me.  We just got done memorizing times tables though.  I think division is later in the year.  Socially he does okay in school.  He is a bit quiet and doesn't like a lot of attention on him but he has friends.   The teacher says she has to ask him questions specifically to get him to talk in school.

[Sandman2]

   Outside of the problems that you have mentioned - how is he doing at school?  Particularly grade wise?  He is probably in 4th grade?  How did he do with long division?

[specialmom]

I agree with Mark Lakewood---  especially since you had such great success in the past.  I also have a 9 year old boy.  Wow, have video games and tv picked up a pretty significant audience with that age group.  And most of his friends are probably really into it too.  So, don't feel like it is just him.  One thing that helps me with that is to have him in extra curricular activities.  My son swims, is in cub scouts, plays an instrument, plays basketball in winter, baseball in spring summer and flag football in the fall.  It really does help to have him involved in things even if it is just his choosing one or two and not as many as my kid.  

But again, since you had such good success with your psychologist, I'd go back.  The subject of not winning and showing his displeasure is something many kids do but sometimes it is a sign of perfectionistic tendencies and anxiety.  So, it is best to find out what is beneath it to properly address it with a child.  If it is just bad sportsmanship, setting boundaries for what is expected helps.  If it is deeper than that, the psychologist is very valuable in those situations.  

Best of luck to you.

[allmymarbles]

Before our reliance on psychology, when a person misbehaved (adult or child) people did what came naturally - they reacted with instinctive displeasure. They shamed them, or made fun of them, or got angry. I admit to being a primitive. If the situation is not terribly serious, dealing with an undesirable personality trait for instance, I meet it head on. that tends to nip things in the bud.

[MarkLakewood3367]

Since you have concerns regarding your son's behavior, you might want to bring him back to the child therapist.  It sounds as if his issues may be too complicated to solve in a forum.