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What was your reason for having Dicks character be such a womanizer?
I don't think he is a womanizer, at least not in the traditional sense that most people use that word. He doesn't lie about who he's with. He's been exclusive for periods of time. He's never cheated on any girl. He always calls the next day. Etc.
Dick has tremendous respect for women, in my opinion. And that respect makes him interested in many women for each one's very different qualities. And that fundamental respect (alongside his other attributes) makes him extremely attractive to a diverse group of powerful women, who know he's secure enough not to require them to be 'less powerful' when dating him.
Also keep in mind, he's still pretty darn young. Should he really be settled down by age 19? I just don't think he's quite ready to settle down, and obviously Barbara agrees.
As for why we made that creative choice, given his history, it just seemed right for the character.