Centerstage - Chicago's Original City Guide

Dear Pulley-Whipped,

Sincerely,
Not That Into Her

A: Since you had me at "Dear Pulley-Whipped," I'm going to assume that a person with your kind of charm attracts all kinds of people, even some card-carrying members of the doucheoisie (and lowly sex columnists in Chicago). In addition to ones you've already tried, some other, less-popular passive-aggressive ways of breaking up with a friend are as follows:

1) Become a Scientologist
2) Start every sentence with "I read in Oprah Magazine..."
3) Delete her email/MySpace/phone number. When she questions you, don't respond in English.

Really, though, I applaud your efforts to try to spare this girl's feelings, but knock it off. Some people are just too dense or naive to pick up on subtle hints that you don't want them around. (I'm looking at you, Al Gore!) If you've ignored her as long as you could, then you need to be more blunt. It's not hip or fun, but it gets the job done. Try something like, "I've found someone else. I'm sorry. Do you mind telling the kids?" Or, "We're too different. I like Gwen Stefani's newer stuff and you're stuck in a No Doubt downward spiral." You don't have to have a talk per se, especially if she's a "peripheral" friend. Send her a firm, though not belligerent, email telling her to back off.

Hi Anna,

Sincerely, Player Baiting

A: As I often tell my YMCA tee-ball pupils, "sometimes it's better to keep it in your pants." You can apply the same logic to your situation of dating multiple people, Player Baiting. Unless you've developed a scorching case of crabs or are R. Kelly, it's probably best not to go into too much detail about other people you're seeing or doing. There aren't many set rules or guidelines for dating multiple people, however, (unless R. Kelly is one of them) so you'd be wise to inform her about how you operate if you want her to stop sharing with you. It's not like you're disarming nuclear weaponry; this is dating, and casual dating at that. You CAN make your own rules in certain situations, as anyone who has ever played a drinking game will tell you. Try making a list of what you think is acceptable to share and what would be a deal breaker. You're presumably trying to avoid feelings of jealousy, which is difficult enough when you're juggling more than one person; unless she's sharing too much to be vindictive or spiteful, which she probably isn't, she probably just doesn't understand how it gets your goat to hear about her tandem hang gliding date with Steve. For instance, I just said "get your goat," which would be a total deal breaker if I were dating me. And a rule has been established. It's that easy. Now go on and be your own spectacular, rule-making self. You deserve it, player.