Some people (let's call them subjects) just don't like their photos - no matter what. Why? They can't decide, they relegate that responsibility to someone else. They want others to like it for them.
If that someone else likes the photo for them, a decision is made and everything is fine. If the other person doesn't want to decide, the subject is left hanging.
The skills of a photographer, both technical and artistic, play a role in making good portraits, no doubt about it. That's half of the story (not 'just the half') because I don't mean to undermine the first half, to project the importance of the second half. We are talking about being able to decide, liking ourselves, accepting ourselves as we are. As long as we don't like who we are and how we look, nothing else matters.
Some people have had protective upbringing. All decisions were made for them out of love and affection of course but that turns out to be a bad thing when they grow up. They can't make decisions for themselves, they depend on others and sometimes the parents are not available so they are left high and dry. They can't decide if they like their own photo no matter how well lit, how beautifully that photo presents that person. That's unfortunate but is true and prevalent. Knowing this helps somewhat.
Speaking of liking your own photos, be sure to check out this gallery of photos liked very much by those persons in the photos. I am here to take yours too. Call me if you want me to. Thanks for reading!