What non-physical thing his insecure about but you love:

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James: his humor, he told you this when you were having a deep conversation. He said to you that after a while of getting shut down by Lily he thought his jokes where annoying to people. Much to his surprise you told him you loved his jokes.

Sirius: his background, he thought it would define him as a person. You told him "nothing can define you when it comes to those who  care about you."

Remus: his leadership, not only as a prefect but to others in his year. You told him that he is a natural born leader even though he doesn't see it yet.

Peter: his knowledge, he doesn't think he's good enough for you or the Marauders but you constantly tell him how proud you are of him and it always makes him feel better.

Lucius: his athletic abilities, you thought he was good at quidditch and he never bothered to try out because he was worried he wasn't good enough which was one thing he regretted.

Snape: he thinks he dumb, you reassure him that he is so intelligent and smart and capable of so much more.

Frank Longbottom: he is always worried about what others think about him. You would kiss him and tell him that "if others can't see great things that I see in you, then it's their loss."

Regulus: he thinks he's not serious enough. Although, how you see it is if there's a serious conversation you have to have with him. He listens and understands.

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