Most Helpful Guy
I had this really bad. When I was younger I had as close to zero self esteem and self confidence as you could get. I had Hyperhydrosis of the hands which meant my hands would sweat. I filled one of those small dixie cups in less then 2 min, that is how bad. I closed myself off from the world. I never really had friends. How could I have a girlfriend If I can't hold her hand because she would be grossed out.
the first woman I found that wanted me I married. We were together 25 years but in a hugely co-dependent relationship. I knew she could do better then me so I let her make all the decisions, I gave up everything I liked that she didn't, I did everything she wanted to do... hoping that would make her happy and never leave me. well that didn't work. I did finally get a decent therapist that helped me a lot. What truly made a difference was online dating. if I unhide my profile I will have multiple women within 2 days to chat with. i can have a date or more within a week. out of 9 real dates (that went to at least a 2nd date or more) I slept with 4 of them. 3 on the 3rd date and 1 in place of the first date. My self esteem and self confidence skyrocketed. But because it was at zero it is at a healthy level. I just broke up with a woman at the beginning of Feb and my thought when I decided to finally end it was "I can just find someone else". I had another date set 2 hrs after making the call to break it off with her.
There really isn't anything you can do. He has to be willing to make the move. he really should talk with someone. It is really bad if other women friends of hers are telling the guy "look she will say yes if you ask"...
the biggest question I have is "why hasn't the woman asked him out?" You want to do something to try and help him... have her go after him. there is nothing hotter then a woman making the first move. first kiss, asking us out, making the first sexual advance...
her going after him could be enough to change things...
Most Helpful Girl
maybe the guy who thinks he is not good enough for her, know it deep down.
I have had many experiences, where I, a woman, just had to let go of many potential partners, because I knew that WE WOULD NEVER BE GOOD FOR (AND GOOD ENOUGH) FOR EACH OTHER.
If you know that it would do more harm than good to be with someone - then it is not a self-esteem issue, rather a WISE DECISION FOR YOURSELF AND THE OTHER PERSON INVOLVED.
Maybe you could be reading this guy wrong, or maybe he generally lacks a true belief in himself, the answer to your question is in the question.
And you cannot talk to the guy about him, he has to go on this self-discovery journey alone, to realize his own worth.
Focus on yourself and your own relationships.