Dear Playboy Advisor: Questions From Men and Women to the Advice Column of Playboy Magazine

CONTENTS

INTRODUCTION

In 1997 the
New York Times
asked me to share the most memorable question I had received in my role as the Playboy Advisor. Here it is:

 

Each summer, I drag a recliner into the woods near my house. When I feel horny, I sit in the chair in the nude and spray insect repellent every where on my body except my genitals. Is this normal?
—G.B., Fort Lauderdale, Florida

 

My response was simple. I asked G.B., “Have you seen any other chairs out there?” If only every letter were so offbeat. Instead, I feel a tinge of anxiety each month as I read through the new batch of reader mail. Will we receive enough questions that we haven’t already answered? There’s reason to feel insecure. Since the Advisor debuted in September 1960,
Playboy
has published more than 6,500 questions, of nearly 400,000 received. And yet, month after month, the magazine’s readers surprise me. This book contains the most interesting, enlightening and entertaining letters of the past decade. I hope my responses can be described the same way, although when I am too flippant, or cross that line between being honest and brutal, I am sure to hear about it. The readers keep me honest, and informed.

To prepare the first column, the editors solicited questions from friends, including whether to wear a tie with tweed, whether the salad is served before or after the entrée and whether one should answer the phone during sex. Sixty-three readers wrote in before the next issue—a rousing response. (The number of letters has been carefully tallied ever since. Today we receive 100 letters and 500 e-mails each month, nearly all of which receive a personal reply.) The wide range of subjects covered in the column—we have promised for 45 years to answer “all reasonable questions, from fashion, food and drink, stereo and sports cars to dating dilemmas, taste and etiquette”—reflects the magazine’s belief that a person interested only in sex isn’t very interesting. But that policy also leads to ribbing. Jay Leno, for example, once asked on
The Tonight Show
, “Did you ever notice the Playboy Advisor tells you about your love life and your car problems? Do you generally go to the garage and say, ‘Clem, I’m bothered by sexual dysfunction’?”

The most interesting part of writing the column is the dialogue that some topics provoke, such as whether masturbation is cheating on your spouse with your hand. About 30 percent of the letters we receive are from women, many of whom pick up their husband’s or boyfriend’s issues but many of whom subscribe on their own. Their contributions are invaluable. The most common question, without a doubt, is a simple one: Am I normal? Inevitably the answer is yes. Or, at least, you’re as normal as you need to be.

Some readers wonder what makes me qualified to be the Playboy Advisor. When I appeared as a guest on
Politically Incorrect
a few years ago, comedian Paul Rodriguez asked this question directly, saying, “Who died and made you Sex God?” No one had to die. Because I am a journalist and not a doctor or academic, I don’t presume to know anything. Instead, my skill is that of a perverted reference librarian. I can find someone qualified to answer even the most offbeat question, and I’m not shy about asking. That is what
Playboy
makes me say, anyway. The reality is that I do know everything, and that I am the world’s greatest lover.

Thank you to the thousands of readers who have shared their knowledge, experiences and questions over the past four decades, including Barry Manilow, who wrote in 1965 to ask if he should leave his day job to pursue his musical wild oats. (We told him to go for it.) Keep the letters coming.

Another batch of mail has arrived, so it’s time to sit in my chair in the woods. You pick up some strange habits at this job.

Chip Rowe
New York City

AFFAIRS

Is it cheating? Ask your spouse.

What is this guy thinking?

I had an affair with a guy for two months, but a girlfriend told me afterward that I did some dumb things when going about it: (1) Since he’s married (so am I), he didn’t want anyone to see him sign into the motel. So he had me do it. (2) He paid for the room the first time, but thereafter let me do it. (3) He always said he had to hurry home because he felt guilty. He wouldn’t even walk out of the room with me. I always checked out by myself. (4) We never went anywhere because he was afraid someone would see us. We would only meet every two weeks, even though we live near each other. (5) After I got home I would e-mail him sweet things but would not hear back from him for days. I know the problems are glaring. But can you tell me, from a man’s perspective, what he was thinking?—K.C., Cleveland, Ohio

You wanted romance, he wanted sex, and he got what he wanted. Plus, you picked up the tab. Throw in a massage and an order of wings and you’re every man’s fantasy. You might do better telling your husband what you want, and asking what he wants, and figuring out together how you can provide for each other, than looking for answers in a motel with a guy who treats you like a prostitute. FYI: He didn’t feel guilty, and he had done it before.

She fantasizes about cheating

After we’d fought, I invited my girlfriend over so I could apologize. We ended up having great make-up sex. The thing is, we fell into this weird cheating fantasy. She kept saying things like, “I hope your girlfriend won’t mind me sucking your cock right now” and “I can’t wait until the next time my boyfriend and I fight, so you can fuck me.” It spooked me. If she gets off on the idea of cheating, maybe she has already cheated, or she will. I was hoping that you could give me your take.—M.E., Shelton, Connecticut

If your girlfriend were cheating on you, she wouldn’t need to fantasize about it. Encourage her to tell you more of her bad-girl fantasies, then make them happen. Try this: Call her at work at noon and give her a room number at a nearby motel. Be waiting for her there in a suit. After your quickie, hide her panties. Back at work, she’ll think about you every time she shifts in her seat.

Is a cheating employee bad for business?

A woman who has worked for me for 12 years is having an affair with a service technician who visits my shop. Her husband also works for me. I am concerned that if or when she is caught, she and her husband will both quit, which will be bad for my business. I’ve become involved to the point where I schedule the husband’s business trips to coincide with when his wife is over her period so she and the tech can more easily have sex. My questions are: (1) Do you have any statistics that report the outcomes of these situations? (2) Should I be this involved? I am a married man who several years ago also had an affair with this woman, but it ended without anyone knowing.—C.F., Seattle, Washington