Or, "How To Trick Cute Funny (Probably Soon-To-Be-Famous) Boys Into Meeting You Out For Tater Tots In Six Easy Steps."Step One: Blog about comedy in Chicago, link to a NYC comedy blog.
Step Two: Have NYC comedy blog e-mail you to ask you to run their Chicago branch. Accept offer. Meet cool local girl already knee-deep in the scene, kick off new venture together.
Step Three: See local comedy shows. Notice outstanding performers in those shows.
Step Four: E-mail one of them, and be all "I'm sort of a journalist, and blah blah, and do you want to be interviewed?"
Step Five: Meet unsuspecting boy in local diner, acknowledge right off the bat that you're new to all of this and totally making it up as you go. Enjoy his joke about it being a form of improv, interpret his lack of running away as cue to continue.
Step Six: Order tater tots. Proceed with "interview." Wonder why more people aren't doing this.