A Lesson In How Not to Be

How not to go about asking someone out.

Woman to Women

How to Break Up Before You Begin

A lesson in how not to be

-Judy McGuire

nerdy manEvery Friday morning I do a spot on a radio show called The Ladies Room on 92.5 FM, out in Seattle. The two hosts, Brooke and Monti are completely adorable and hilarious. Monti’s off the market, but Brooke is still dating so she had a question for me this week. She was out having fun last weekend and apparently randomly chatting up some dude. I guess she told him she worked for the radio station and he tracked her down to ask her out. She asked me if she should go out with him even though she couldn’t recall what he looked like (hullo, demon liquor!).

Monti and I both encouraged her to go. I mean, seize the day, whatnot. Below is their correspondence (printed verbatim) – and be patient because the payoff is well worth it:

Sent: Wed 10/8/2008 8:26 AM
To: MOViN 92.5 Ladies Room
Subject: MOViN 92.5 Comments From The Web

I was listening to your station for the first time this morning, I turned it on because I met Brooke on Saturday at the Tractor tavern. So this message is really for Brooke. As I’m listening I happen to hear that you’re looking for a boyfriend. I’m not sure if you remember me or not but I’m the guy that works for Apple, made a comment about the hats my friend and I were wearing. We also talked about your friend who was suppose to do a comedy bit but was pasted over on the schedule. I’m sure this e-mail is a little forward, but you left the tractor before I could ask you out in person. How very strange that I am sending an email to radio station asking you for a date. Whatever.

P.S. this is not to be used for on air laughs.


On Oct 17, 2008, at 7:16 AM, BROOKE FOX wrote:


Yes I remember hat man! I’m totally down for meeting up for coffee or something. You have to be warned that everything in my life is used for on-air though. The good thing is that I’m the one that makes a fool of myself 98% of the time so that only gives you a 2% chance of being used for on-air laughs. Pretty good odds I would say.

Let me know what your schedule looks like.


Sent: Fri 10/17/2008 8:51 AM
Subject: Re: MOViN 92.5 Comments From The Web

To be honest I am in no shape to go out with anyone. My heart belongs to a woman who right now only wants to be my friend. I emailed you because she said that I should try to date other people but the truth is, that would be fair to no one. The love of my life deserves more from me than that. The sad fact is that she broke up with me because I was an asshole and now I’m resting at the place where disappointment and regret collide. All I think about is her, and I’m convinced there is no one on earth that can compare to her. I’m trying to do everything I can to win her back because she is my soulmate. I know my email is long and more than likely goes into way too much detail. I should not have emailed you in the first place. This has nothing to do with you and everything to do with me. There is only one woman I’m looking for and currently she’s not looking for me.


Ouchie, Brooke! Dumped before the first date by a tragic someone whose face you can’t even recall. Sidle up to me at the resting place between heartache and heartless laughter and let me pour you a cold one.

Ladies and gentlemen, let this be a lesson: If you’re going to break up with someone before you’ve even gone out on one date with them, you’re probably going to be the butt of somebody’s joke.

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