Working as an editor and writer at Playboy was just a job, except when it wasn’t. A series of personal essays on navigating work and life. Produced in partnership with NewCo Shift.

For a period of a year or so I was the Playboy Advisor. The Advisor was a longstanding advice column in the magazine penned by mostly anonymous writers. Various people and teams wrote it over the years, with one writer clocking over two decades of service. For the past two years or so women have written the Advisor, with their names attached to each column. But up until then, the Advisor was essentially a Playboy-esque omniscient narrator and confidant, presumably male to those on the outside, a balm and advice-giver to the adrift and befuddled American man (for the most part; sometimes women did write in). The Advisor would explore, over and over, among other things, questions relating to penis problems, threesome wishes, stereo speaker positioning theory, and four-in-hand versus windsor knot tie-tying arguments.

At its peak, when the magazine was selling upwards of 7 million copies or so on the newsstand in the early 70s, the Advisor had a staff of five writing it, or so I was told by an old timer as it was handed to me one day as an additional task in an already busy job. As he described it to me: “You’re the cool uncle giving advice to his nephew. Good luck.” This was a number of years ago and the printed magazine advice column as we know it was a dying model in the internet age, with more relatable individuals, like the Dan Savages and Dear Sugars, being very direct and personal in their advice. But the Advisor was still kind of a cool throwback of an institution. A masculine-centered Google with opinions. A pre-search engine search engine with the taste and perspective of a worldly bon vivant, along with a vast lending library at his disposal and infinite time to peruse it for you.

The questions came in the form of letters, mostly (though there were emails). Stacks of hundreds waited for me when I started. Tilting sliding stacks of envelopes taped, and licked, and sealed, and placed in mail bags and boxes. So much brittle glue, activated by saliva, the now-dry paper warped from the application of a person’s wet tongue on the other side of the country.

In the old days the Advisor would answer every single letter, even if the answer wasn’t published in the magazine. On my first day as the Advisor, the editorial assistant who had been opening the mail for the previous writer brought the letters to me in three overstuffed manila folders. This was the first line of defense. One folder was for yes’s, one was for maybes, and was one for outright nos. The “no”s were the least tidy, the most wrinkled, the least legible, the rambling two-sided screeds, the kind of letters that no general reader would relate to.

“You might want these,” the assistant said, handing me a box of latex gloves. “Why?” I asked. “You should ask the guy in the mailroom about the letters he’s handled,” she said. “Trust me.” When I asked the mailroom guy what the assistant meant, he told me a story about a centerfold spread from our magazine that had been torn out by a reader and sent back stuffed into an envelope. When he tried to open up the pages, they resisted, and he realized too late that they were stuck together, adhered by something now brittle and when he pulled the pages apart they yielded with a crack.

Going through the letters, I started to see patterns: there were the postcards written in scribbled, demented hand writing over and over from a man who was obsessed, surprise surprise, with breasts. His questions were about the motivations behind why various women he’d come across in his daily life would dress a particular way, as if the advisor had some sort of time machine as well as mind reading capabilities. There were the prison letters penned and sometimes improvised with coffee on scavenged paper, written by men with less than most of us can imagine having. More than one presented supposedly exonerating evidence. Many men wrote about their pain over learning they’d been cuckolded. Some men expressed a desire to watch their wives cuckold them. There was the guy who sent in emails with descriptions of outlandish sexual situations, with him playing the starring role. They verged on Penthouse letter soft-porn descriptions, and it’s clear he was punking Playboy, and his letters went unanswered. People would write repeatedly about how the fine print at the end of the column said that every letter would be answered and why had they hadn’t gotten a response yet? It would’ve been impossible to meet the demand, so we took that fine print out.

The easiest questions to answer were the ones about food, drink, and fashion. For every question about how to handle knowledge of a cheating spouse, or how to approach a woman when you have crippling social anxiety, or how to stop obsessing about someone who’s rejected you, there were the questions about the value of a pre-prohibition bottle of bourbon, or whether it was okay to wear a bolo tie with a tuxedo, or how to get enough protein when you’ve turned vegetarian. Since some of these questions would come in through email, I knew that the people had access to Google and could research this for themselves. And there was something quaint and reassuring about the thought that people would still entrust a magazine with answering a question better than the hive or crowd mind or Quora. It felt like an honor. And these were questions that could be answered definitively, at least if you took the position of Playboy.

As for the sex and relationship questions, at first I worried I wouldn’t be able to help the letter and email writers. “Why me?” I asked my boss. And he said something along the lines of how I was the only guy on staff who anybody might trust with matters of taste. He was flattering me in lieu of a raise. He said I knew about cool gear and what whiskey to drink. I reminded him that half the questions were about sex and relationships. He said nobody who’d written the column before had been a therapist. “It doesn’t matter what you say,” he added. “As long as it’s entertaining.” Which he knew as well as I wasn’t entirely true.

Reading through the stacks of letters was overwhelming: it seemed that, through the filter of these letters and emails, all the world was doing was trying to have sex and not getting it, having sex and not enjoying it, loving sex and wanting more of it. Whether over or undersexed, the world was unsettled.

As writing the advisor was one sixth of my busy job, I reverted to a triage that seemed to work. More than one reader accused me of being the whimpiest, softest advisor they’d read. Two said I must be a woman. I take that as a compliment. While I’m sure there are more experienced advisors out there to tell you how to be an advisor, I did the job by making sure to…

Treat Everyone Like They’re Friends and Family

These people are children, brothers, sisters, fathers. I found that by thinking of them as blood and I could tap into empathy and respect automatically.

Be Kind

Judging from the letters we got many men think their penis is too small. Every week they’d write in with their measurements asking where they stood on the spectrum or they’d say their girlfriends said they were big enough, that that they’d read the studies and still didn’t believe that they were okay. I’d write every about the latest penis length studies every few months to make them feel a little better.

Be Relatable

Even though the Advisor was anonymous, I’d respond with parallel stories of people having gone through the same challenges — whether it was a happy ending story about having a lost job and having gotten another one through patience and effort, a better relationship after a dishonest one, finding a lover who accepted their body type. You’re not alone and this will too will pass was a note I hit a lot.

Encourage Therapy

Actual professional mental health support saved my ass personally when I was going through a time that was unmanageable. Without using the first person “I” I’d say as much. Advice columns are there to sooth and educate and entertain the reader, not provide actual medical mental health advice.

Listen for the Answer in the Question

Most letter writers knew the answer to their question and would reveal it without realizing it. It was my job to lead them toward their own solution.

Present a More Focused Question in Return

By doing so you’re leading someone to an alternate line of questioning and leading them to a more focused self-assessment and gut answer informed by research. You’re breaking someone out of a closed loop that they can’t get out of.

Present Research and Resources

I searched for and would present primary sourcing and studies that would put their problem or question in a broader context. I’d share links to research papers, non-profits, support groups, and other free resources that would help them further inform themselves and study possible decisions and actions.

Go There, Without Judgements

And since the questions determined the research, sometimes the research involved heading into worlds I was entirely unfamiliar with. Such as the vigorous debate surrounding the potential health benefits of prostate massagers, why hand-blown glass dildos are more eco friendly, and the psychology of cuckold fantasies. I’d educate myself as dispassionately as possible. Present the facts. Then clear my browser history.

Know that the Answer Isn’t Ultimately the Answer

People writing in to an advice column on some level know that the advice columnist is not going to solve their problems. I answered hundreds of questions and for the year or so I wrote the column I worried that I’d get a complaint email or letter for having given bad advice. Simultaneously I was hopeful that I’d get a thank you note for having solved a problem. Never once did I — or I should say the Advisor — receive either. This leads me to suspect that the mere act of writing to the advice columnist is the reader’s first step to solving their own problem. By simply posing the question they’d already embarked on a quest that was ultimately theirs to complete.