[Dart]

I'm a beginner, so maybe my advice will suck. But, I see this differently. When I was a complete newbie with approach anxiety, I approached whichever girls looked most approachable. Approachability and attractiveness are different things, and I'm not sure whether there is a strong relationship between the two. I never gave it much thought. At that stage, I simply needed to get over my fear of talking to girls. When I went out, I spent a lot more time walking around looking at girls than actually talking to them, and there were many girls I failed to approach because I was too afraid. Nevertheless, I gradually gained experience with talking to girls, and I gradually got over my approach anxiety. I didn't have a wingman pushing me to approach, but I'm not really sure whether it would have made a difference. Maybe he could have forced me to progress more quickly. But, it's possible he would have hindered my progress by increasing my stress level. I really don't know. Regardless, I have no significant approach anxiety anymore. I simply approach any girl who looks attractive. I never consider not approaching a girl because she is somehow too attractive. I just don't think about it in that way. When a girl rejects me, I just learn from the experience and do better with the next girl.

My advice is that you first focus on approachability rather than attractiveness. Don't steer him away from attractive girls or towards unattractive girls. Just steer him towards any girl who looks like she's open to being approached by a guy. Later, once he begins to enjoy approaching more than he fears it, encourage him to approach any girl he is attracted to. Don't put an unnecessary fear in his mind that a girl is out of his league. Also, don't pressure him to approach any and every girl regardless of attractiveness.