How <I>Not</I> to Date - An Interview with Judy McGuire

Judy McGuire has a way of giving advice that is never condescending, comes from the heart, and experience, and is actually helpful, which isn't anywhere as easy as it looks.
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Judy McGuire is who I turn to when I am having relationship problems, and believe me, I have a lot of them. She has a way of giving advice that is never condescending, comes from the heart, and experience, and is actually helpful, which isn't anywhere as easy as it looks. So I was thrilled to read her hilarious new book, How Not to Date, just out from Seattle's Sasquatch Books. If you hate dating books, you're still pretty likely to like this. Another thing I think is awesome about Judy is that she never bullshits. So check out her blog, her Dategirl column in Seattle Weekly, and her book to learn how not to make a fool of yourself on your next date, lest it be your last.

How old are you?

Forty-three. Though I believe a careful combination of spendy moisturizers and sun/cigarette avoidance allows me to pass for forty-one-and-a-half in certain lighting situations.

Who was the first person you ever gave dating advice to, and what was it?

I went through a protracted, excruciating period of befriending crushes and then giving them advice about the girls they were hot for. Oddly enough, that girl was never me. So I guess that started in high school and I finally wised up and quit being friends with men I wanted to sleep with at some point during my early thirties. I guess you could say I'm a slow learner.

Are you better at giving dating advice than taking it?

Ha. Like most people, I'm way better at doling it out than taking it myself. I seem to have a common-sense block.

You've been writing your Dategirl column for eight years. Has the nature of the questions you get changed over the years? What's the most common question?

From jump, the most common question has been "how can I meet someone?" But people tend to tack on a bunch of caveats like, "but I hate bars, refuse to try online dating, only like redheads, won't date outside my religion/race, etc.," which just makes me slappy. It's hard enough to meet someone you don't want to punch in the face; to also require that the person meet a bunch of arbitrary requirements is just insane.

Your new book, How Not To Date, is in many ways an anti-dating guide, or perhaps it's about learning from negative examples. Why did you choose to structure it this way?

I've always found reading about and learning from negative examples to be far more effective and fun than plodding through some cheery instructional manual. Plus, who wants to hear about a bunch of great dates with inspiring outcomes? This book doesn't promise to find you a date, but it will give you tips on how to avoid fucking things up beyond repair.

Were most of the contributors of horror dates your friends, or strangers? How did you go about finding them?

I told everyone I knew that I was looking. Some were friends, then there were friends of friends . . . others were recruited through my blog and still others I tracked down because something about them appealed to me. Like Dan Renzi, who used to be on the Real World. I love his blog and asked him to participate. He agreed and I'm so glad--he's hilarious and should be a giant star.

In addition to the many dating don'ts, you also have interviews with people like porn stars Joanna Angel and Tera Patrick, DJ Kurt B. Reighley, shrink Rob Dobrenski, PhD, and a former stripper. What was the most surprising thing any of them said?

The most surprising was that while Tera Patrick said she'd reject the wee of wiener, Joanna Angel was more concerned that the person she was dating be charming and able to carry on a conversation. She said she that her sex life was so amazing at "the office," physical chemistry (and a giant cock) were less important off-screen.

Out of all the awful stories in the book, which would you single out as the most awful, the kind you wouldn't even wish on your worst enemy?

After all my research into bad dates and eight years as a dating columnist, nobody has managed to top the guy who crapped himself in my bed.

Was there anything too horrifying to include in the book?

Personally, I didn't find this at all horrifying, but one item in my list of things you should never tell your date made my editors weep like little babies and they asked me to take it out: "I have enough extra skin around my testicles that I can wrap it around my hand like a mitten."

Maybe it's a guy thing, but I found it kind of charming.

My favorite part is about how your current boyfriend, Spyro, actually committed a dating faux pas (having his friends tag along on the date), but you forgave him enough for a second date. When should you let a mistake go, and when should you give someone another chance?

Spyro was freaked out when he discovered that I was a dating columnist, so he decided to protect himself with a wall of friends. Once he figured out that our date was actually a date and not a research expedition, he relaxed. He was such a goof about the whole thing it wound up being kind of charming. Plus, men are never intimidated by me, so that was refreshing!

I think people don't rely on their gut nearly enough. If you have a good feeling about someone who suffers a momentary spazz-out, then give them another chance. But if your gut is saying no, listen. I certainly could've saved myself a lot of trouble that way.

Who would you say is your target audience for How Not to Date?

Anyone with $16.95 in their pocket.

Is Valentine's Day a terrible time to pick someone up, or the perfect time?

I know it's probably wrong for a dating columnist to feel this way, but I really loathe Valentine's Day. Any holiday specifically designed to make single people feel like crap is one I really have no use for. And yeah, I realize it's not about that--it's ostensibly about celebrating love, whatnot--but too many women wind up crying into their cocktails because they don't have a boyfriend or husband to buy them an ugly stuffed animal clutching a satin heart. So I guess if you're a guy who's into picking up the depressed, drunk and vulnerable it's a great time!

And now some questions for the aspiring writers out there; how did you land your Dategirl column, and what's been the secret to your longevity?

I've been a writer for a long time, but never wrote about relationships until a cartoonist friend and I decided to do an animated series called Dategirl. Richard Mather, the cartoonist, and I got a deal with MTV to do the series, which was about a sex and love advice columnist who lived in Williamsburg. I was all excited, quit my academic job researching heroin addicts and prepared to become the next Matt Groening.

After nine months of development, MTV passed on the show. Oopsie! Meanwhile, I'd met another Richard -- Richard Martin -- who was then an editor at the Seattle Weekly. He suggested I just become the main character in the TV show and try out as their new sex columnist. So I did and got the job.

As for the question of my longevity--I honestly have no idea, but am convinced that with most good things, luck played a large part.

How did the book deal come about, and how long did it take you to write it? What was the most challenging thing about the process of writing the book and getting it out into the world?

The book came about while I was on vacation. I got an email from Terence Maikels at Sasquatch Books (a Seattle publisher) asking if I was interested in writing one. Um, okay!

The actual writing was the easy, fun part of doing the book. I'm a fairly quick writer and I love interviewing people and hearing their funny stories, so that bit was cake. Sasquatch is a small press, so I didn't get lost in the shuffle, which was great. Everyone from the publisher to my editor to the production staff was completely supportive and kind.

By far, the most difficult part has been promoting the book. I'm actually fairly shy and so the process of pushing myself into the spotlight has been excruciating. Anyone who thinks the book-writing process is over when they type "The End" is sadly mistaken.

How Not to Date was recently featured in People magazine in a roundup of Valentine's Day-themed books. How did this come about, and what kind of feedback have you been getting?

I have two lovely friends who are photo editors at People. When they heard I was doing a book, they volunteered to walk it down to the books editor and plead my case. For that I owe them my first-born. The book editor decided to run with it and so she can have my second. As I'm not actually having babies, I think probably a thank you note will have to suffice.

It's astonishing what one little blurb in People will do for sales. My Amazon ranking rocketed. I don't know how that translates into numbers, but I suspect it's a very, very good thing.

Since Britney Spears was on the cover of that issue, what dating advice would you have for her?

Oh, poor dear, Britney . . . the girl needs to be medicated. She needs a solid course of pharmaceuticals and intensive therapy before she should even think about dating. And for chrissakes, somebody hook her up with some birth control.

What's next for you?

A few years ago I collaborated on an odd kid's book that's currently being shopped around. I have most of another proposal done, but it's still in need of tweaking, and am trying to find the time to flesh out some television proposals that this amazing production company is interested in. Mostly I'm kind of overwhelmed because while doing all this, I need to make some dough and am also doing a bunch of marketing writing.

I'm really lucky that I get to do something I love, but sometimes it's hard to organize your life in a way that makes it all happen and allows you to pay the bills. At least for me, anyway.

Lastly, at your New York book release party on Wednesday, February 13th, you're getting people (including me!) to share bad date stories. If someone's not in New York, how can they share their bad date story with you?

Oh, please share! I can never hear enough bad date stories--it makes me feel less alone. Go to my blog and leave them in the comments or email me at judy.mcguire AT