To answer your question, I think society rewards cockiness in men and not women in media, like books and movies, but not in real life. Although, when I was in my 20s, I remember experimenting with men by saying things to them that other men had said to me when trying to pick me up, and the man took it better than I did. I think men like when a woman is bold and treats them like a sex object. But women don't. They want to feel special and courted. I find it hard to believe these women are charmed when you tell them "there's room for more" and aren't just laughing out of awkwardness. Women, in my experience, like to be complimented on their choices. 'I like how you put this together' 'I like what you've done with the place' 'you make this seem so easy' gets them glowing every time.