Just because I don't want to be complimented all of the time, doesn't mean I want to be insulted instead.
My Senior year in high school involved this unnecessary class that tried to mix freshmen with upperclassmen in hopes of bettering the society in which we were educated. Though it did not succeed for me personally, it did bring one good thing. While the class was being substituted one day, a couple of guys decided to skip their assigned placement to be with their buddies in the classroom where I happened to be. Upon noticing me sitting bored as fuck in the back, one of the gentleman sat in the desk between his friend and myself, turned to me, and said, "Hey Chun-Li, turn around and let me see that boot-TY," and sweetly smiled. Obviously the insult here is the racist card. But instead of laughing at their own "joke" and waiting to be basked in glory by their homeboys, this guy just smiled. I, who is hardly ever offended, was not offended by this and just giggled. Long story short, the person who ran up to pose with his arm around me when my name was announced Prom Queen, was him, my senior-year-in-school-boyfriend, number one. (:
Though no one has yet topped that insultingly smooth moment, there was another guy who simultaneously insults by mockery and charms by mockery. Mockery, which is something considered to be very annoying, has turned into something that genuinely makes me smile in that Am-I-a-stupid-girl? kind of way when it comes from this guy. It's hard to explain it in any other way.
And then there's that one situation where I couldn't figure out if I was being insulted or complimented: He told me after I had said something over the phone that I sounded like the girl from Drake's Marvin's Room. That voice didn't automatically register in my head, so I had looked the song up and after listening to it, I honestly can't say if it was a nice voice or a harsh one. Opinions? Well anyway, it was said with a chuckle which made me believe it was an insult. Communicated smoothly. How? Again, it's hard to explain, except with this analogy: when someone foreign speaks French, of which you don't comprehend completely, he/she could be insulting you but it sounds so...nice, and you smile because you believe it was complimentary.
Trying to be funny through sarcastic insults is way overplayed. But being plain smooth while insulting a woman is on a whole 'nother level, and the reason why this is number nine.