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Dear Jessi:
“he actually has a low self esteem”- this is what I thought to myself while I typed the previous post to you. I didn’t express it to you, but I thought it. I don’t think that he “cares about her” as much as that he values her supermodel looks as something that makes him feels more valuable for interacting with her. It is similar to men looking for what is termed a “trophy wife”, it makes them feel more valuable being seen with her.
As a man with a lower self esteem he needs something or someone (interactions with someone, in this case) that makes him feel better about himself.
He may think that you will think highly of him knowing that a supermodel looking woman slept with him, and that could be why he told you that (is it a true story, I don’t know).
anita