yeah something cocky and funny could be.
Me: *hug and slight kiss on the neck*. I guess you can follow directions and look very cute for a date.
Her: well if that how you say i look good. thank you. and you dont look to bad yourself.haha
Me: girl you must not have heard, im the cutest you will see around this neck of the woods.
Her: lol is that right?
Me: oh yes, lol you better ask somebody.
by the way i sometimes do kiss on neck or cheek cause its unsuspecting and it kinds of shocks their system,(like omg,,did he just kiss my neck...god damn what was that, but in their mind they are a little turned on) usually only to girls i know wont get wierded out by it.
I would usually use things like that. things that seem cocky and funny, but im not being a complete asshole about it. i might use your line about the experience thing once i have started the conversation to up the s3xual Tension. Like have you ever felt out of your league when you slept with someone. She might say no or yes but whatever she says. U could then make say something like, oh well you better be ready to cause this old dog does have some new tricks. and then do it with a very warm energy and funny face/tone so its not taken the wrong way cause then its like a challenge for them. Like oh yeah old man, i guess we will have to see.. but right off the bat,NO that would be a little creepy and for sure lower your value