He simply needed a high value/quality woman who knew she was the prize & doesn’t need to chase him . Someone who was real, rare, feminine, & showed him that she wasn’t like the rest. A woman that exuded happiness, so he would be able to give it to her. He could also learn from her that he didn’t need nobody to feel validated, not even from her. His happiness should depend on him . You know you can’t light a candle w/ no wick.
He didn’t seem to like women who knew they were the prize and didn’t need to chase him. He compared those women to cats and thought they were manipulative and playing games.
To me, Siedah Garrett is the closest to being the best match because he admired her talent. She’s funny. She’s nice. She’s straight forward and not playing dumb games. She’s tall and has that sexy, nerdy look he liked.