Thanks for getting back to me on this.
From what you say, he really needs to boost his self esteem a bit. Looking at it overall - he is doing pretty well - make sure he knows that you are proud of him.
His behavior and self doubt are pretty well normal for someone of his age, particularly his doubts about girls. I've been happily married for nearly forty years, and believe me, when I was fifteen, I would never have believed that ANY girl would ever be interested in me, let alone the ballet dancer I married!
Try to ensure that all his achievements (losing that weight, staying off drugs, studying well) are noted and praised.
I'd like him to read this article here:
and secondly, to use this tool:
This Bill of Rights was one of the tools used by Virginia Satir, a well-known family therapist. Containing some really basic psychological rights belonging to every person, it really helps to identify and deal with areas in which we have problems.
Read the statements. Note down any immediate thoughts or feelings that come to you.
Look at yourself in a mirror and read it out loud to yourself. Listen to your voice grow in strength and volume so that you can really start to feel it inside. In the beginning, you may feel silly or embarrassed. You may hear the inner voice say, "That's not the truth". Just hang in there and keep doing it - you'll notice the change within six weeks, if you do it regularly.
1. I do not have to feel guilty just because someone else does not like what I do, say, think or feel.
2. It is O. K. for me to feel angry and to express it in responsible ways.
3. I do not have to assume full responsibility for making decisions, particularly where others share responsibility for making the decisions.
4. I have the right to say "I don't understand" without feeling stupid or guilty.
5. I have the right to say NO.
6. I have the right to say No without feeling guilty.
7. I do not have to apologise or give reasons when I say NO.
8. I have the right to refuse requests which others make of me.
9. I have the right to tell others when I think they are manipulating, conning, or treating me unfairly.
10. I have the right to refuse additional responsibilities without feeling guilty.
11. I have a right to tell others when their behaviour annoys me.
12. I do not have to compromise my personal integrity.
13. I have a right to make mistakes and be responsible for them. I have a right to be wrong.
14. I do not have to be liked, admired, or respected by everyone for everything I do.
Finally, I’m going to suggest that you get a copy of the book “How to talk so teens will listen, and how to listen so teens will talk”. Its ISBN is 13: 978 1 85340 857 1
Not only will it help you to help him, it is also a good read!