Be fair, Jack pretty much spent his teen years that could've been spent learning to be smooth with the ladies being taught to kill Aku. Guy never exactly was given time to learn how to step up his game.

S M O O T H

But seriously Jack you are about 3075 years old.
Why do you still use pick up lines used by awkward 16 year olds?
Step up your game boi, or Logan and Ramirez are so gonna make fun of you at the "Ageless dudes who have way to much free time" meeting.