Guys, What can I do to make a man feel insecure?

It caught me by surprise when my date (for quite some time now) asked me if I found him good-looking. I said yes. He then asked me to rate him out of a scale of 10, and I told him I didn't wanna do so but he was handsome for me. He then told me he was insecure and has low self esteem. He has never ever made such relevation about himself, and I've never heard such things from men before. I felt bad because I think I didn't deal with it right. Now when I remember it, we recently talked a previous date I had. He asked me if that date was good-looking.. and a lot of stuffs along that line.

What are the possible reasons men may feel this way, and what can I do?
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Guys, What can I do to make a man feel insecure?
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