Celebrating 60 Years of the Playboy Advisor

It can be hard to imagine a world in which answers weren’t as easy to come by as simply shouting a question at your phone or across the room. (“Siri, what is shrimping?” “Alexa, can you define spectrophilia?”) But 60 years ago information wasn’t so readily available—especially when the issue involved sex. So when PLAYBOY debuted its Advisor column in 1960, it’s no surprise that it quickly became a popular resource for those curious about sex and how to live the good life.

Each month the Advisor provided a forum where anonymous men and women could ask questions of a dependable authority without fear of judgment. Whether addressing the definition of a flying Philadelphia fuck (fellatio, with partner assists from a rocking chair and chin-up bar) or explaining the nature of the goat’s eyelid (an ancient sex toy), the Advisor was a trusted voice of reason, assuring readers their urges, interests and bodies were, for the most part, totally normal.

“Our mission in life is to make sex better for everyone,” declared the Advisor in 2001, a mantra that holds true today. Yet far from promoting a conquering or cavalier attitude toward sex, the Advisor regularly counseled patience and understanding between partners and would-be paramours. A 2000 study of Playboy Advisor’s first four decades, written by a sociologist and two psychologists, concluded that its content “tended toward tolerance, promoted equality between the sexes and broke down, rather than reaffirmed, stereotypes.”

Below, we look back at some of our favorite reader letters, one from each of Advisor’s first six decades of publication. Here’s to 60 more years of solid advice!

1960s: Looks Like He Made It

In December 1965 the Advisor published a letter from a young man at a crossroads. “B.M.” said he was a rising star in the corporate world who was thinking about abandoning his success to pursue his musical dreams. The Advisor encouraged him to risk it. The young man who took the advice? Barry Manilow.

Q: Music has always been a vital part of my life. Due to financial difficulties, however, I had to stop attending music school and accept a job at a leading radio-and-television network. Through enormous good fortune, I have been promoted very rapidly and at the age of 22 I hold a junior executive position with a very generous salary. The only drawback is that this position has absolutely nothing to do with music. During these past few years, between working and attending college, I have managed to musically direct and conduct three full-scale musicals at various theater workshops in New York. I now have an offer to take this last musical out of town for a period of six to eight months at a good salary with the promise of a permanent position as a musical director. My musical wild oats are screaming to be sown, but it means giving up my secure job. Leaves of absence are rare, so it looks like it’s either one or the other. Any suggestions? —B. M., Brooklyn, New York

A: Follow your real interest and take the musical out of town. At your age, your financial responsibilities are few. If you remain in the secure job, you may regret for the rest of your life that you didn’t sow your notes. You can always go back to radio and television: Your ability was recognized once; chances are it would be recognized again—if not with your former employer, then elsewhere.

1970s: Dress for Success

Kinksters and the sexually curious found a listening ear in the Advisor. This letter from August 1975 concerns a reader’s quest for specialized gear for herself. Sure, it was the “me” decade, but the Advisor was a constant source of encouragement for sexual exploration and the normalization of self-pleasure.

Q: I’ve been reading about a Scandinavian sex device called a grope suit. Supposedly, it will keep a woman in an almost constant state of orgasm. Would you know anything about it—for instance, where I could purchase the device? —Miss F. D., Melbourne, Florida

A: Grope suits came out of the closet after Alex Comfort devoted a paragraph to them in Joy of Sex. In case your little brother stole your copy, Comfort describes the attire as a “very tight rubber G string with a thick phallic plug which fits in the vagina and a roughened knob over the clitoris. The bra has small toothed recesses in the cups which grip the nipples and is covered all over inside with soft rubber points. Once it is on, every movement touches a sensitive area.” Yee-hah. In spite of publicity, it’s almost impossible to find a grope suit in this country. The Sears catalog doesn’t mention one.… Invent your own erotic wardrobe: bikinis made out of waist chains, leather thongs, feathered boas, inflated balloons—the fittings are a gas. In cool weather, an inside-out fur coat is a reliable turn-on. If you believe that less is more, try going out on a date without wearing underwear. You’ll find that clothes can make a woman.

1980s: Hygiene Hijinks

Along with copious queries about positions, performance and penis size, questions about oral sex have been a popular topic in Advisor across the decades. This variation on “don’t eat before swimming” appeared in November 1988.

Q: I’ve heard that it is dangerous to brush your teeth or floss before performing oral sex. Why? —P. U., Dallas, Texas

A: If God had wanted you to floss before having oral sex, he wouldn’t have provided pubic hair. Actually, a recent issue of Sexuality Today warned against brushing before having a bedtime snack—it is thought that you might lacerate your gums, thus opening the way to sexually transmitted infection. Of course, if you never brush your teeth, you won’t be able to attract a partner in the first place. This advice assumes that your partner has an infection. If he or she doesn’t, then continue with your normal program for oral hygiene.

1990s: Orange You Glad to See Me

The 2017 comedy Girls Trip immortalized grapefruiting—a blow-job-abetting move that real-life sex educator Auntie Angel had been teaching for at least a decade prior. In August 1994 the Advisor addressed a question from a reader whose adventurous but misinformed girlfriend turned him into a fan of sexy citrus play.

Q: I thought I had experienced everything in the erotic world until the night my girlfriend came into my bedroom stark naked, holding three large oranges and a knife. She carved a hole in the end of the first one and allowed the juice to drip all over my genitals. She cut the second one into four wedges, squeezed them and licked the juice off my scrotum. She then forced the head of my erect penis into the hole of the first orange, gently squeezing and turning the orange until I came. She halved the third orange and rubbed it all over her body, which I licked clean. Then she asked me to squirt the juice directly into her vagina. Have you ever heard of having sex with citrus fruit? My girlfriend says citric acid fights infection. Is that true? —F. B., Hesperia, Michigan

A: Sounds as if you had a delicious time. Your girlfriend is an inspired and imaginative woman, but her claim that citric acid fights infection is false. Citric acid will sting when applied to a cut, but it is not an antiseptic. However, you needn’t worry about scurvy in the near future.

2000s: Moon Units

The Advisor is well known for respectful guidance on serious questions. But regarding this September 2001 letter, you know what they say about asking a ridiculous question…

Q: My wife told me that my erection appears larger on nights with a full moon. I didn’t believe her, so she measured me every night for two months. And, sure enough, on nights just before, during and after a full moon, I was half an inch longer. Have you heard of this before? Does it have anything to do with the moon’s gravitational pull? —R. J., New York, New York

A: That’s a new one. Does your pubic hair get thicker too? We don’t doubt your penis grew, but the only moon that has any influence on it is your wife’s ass. You both expected it to be larger in the moonlight, which influenced how aroused you became when she prepared you and took measurements. That could easily account for that half inch. Under controlled conditions, there would be no difference. The moon does not move the blood or water in your body as it does the tides, and its gravitational pull is a function of its distance from the Earth, not its phase. Nevertheless, your wife should continue to stroke and examine your erection every day.

2010s: Unicorns Beware

For more than 50 years, the Advisor was a man. That changed in 2016, when the appropriately named Rachel Rabbit White pulled on the Advisor mantle and began addressing topics including toxic friendships, manic pixie fuck-boys, chemsex and this memorable installment on thirsty threesomes:

Q: We’re a heterosexual couple in search of a “unicorn” (an attractive bisexual woman) to join us for a few date nights a week. We’ve had some one-off threesomes but can’t find a partner to join us more long-term. Apps, dating sites, friends, acquaintances—nothing has worked. What are we doing wrong?

A: Unicorn hunters have a bad reputation. Perhaps it’s the polyamorous community’s endless lingo: ambigusweetie, new relationship energy, friends-first swinging and other terms that reek of corporate buzzwords. One has to wonder if all polyamorous people are middle managers. Of the threesome-seeking couples on Tinder, inevitably she is bi but without much experience, and of course he loves to watch. Tina, a former unicorn, has been on her share of “throuple” dates. “These couples are called unicorn hunters because they’re often predatory,” she says. Couples end up treating her like a fantasy rather than a partner; these pairs are simply looking for someone to fill a preimagined role….

To answer your question: You may not be doing anything wrong. Dating itself consists of endless trial and error, as well as numerous bar tabs that never pay off. In ancient Greece the unicorn was believed to be a real beast. In medieval times the lack of proof of the animal’s existence helped move it into the realm of myth. And as you’re discovering, the fantasy of a third person, one who enters and exits a relationship with ghostly ease, is just as unattainable.