Oh dear, sounds like an awfully normal teenage kid. Unfortunately, even the best single mom's don't get exemption from this stage. It may be a bit easier to handle in two-parent familes, who can at least share the burden of strugling to manage discipline. I tend towards the tough-love approach, as Paul outlined. He must know he does not have the luxury option of lazing about and pleasing himself. As Kay says, could a male relative of yours, or of your late husband, join in and help at this stage ? While I agree with lulu that the male model thing isnt the b-all and end-all of the matter, it can often help.
IS it possible that, instead of the empting, almost irresistable option of arguing with him, which tends to lead him into further defiance, you try to chat with him about how he feels about the prospect of leaving school, of taking responsibility for his own life now. What does he want to do in life ? WHat are his interests ? J describes this approach very well. Maybe a counsellor could help you to plan and feel more supported.
Surely his friend is influencing him --- that's what friends do, maybe more at this age than any other. Maybe et to know this other boy a bit better, possibly there are ways in which his example could be used to influence your son for the better ( for instance if the other boy has job plans or activities ).
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