March 2, 2021

I’m hiding my involvement in porn, and more advice from Dear Prudence.

Our advice columnists have heard it all over the years. Each Sunday, we will dive…

Our advice columnists have heard it all over the years. Each Sunday, we will dive into the Dear Prudie archives and share a selection of classic letters.

Dear Prudence,

I am a freelance Web developer who was almost bankrupted by the economic collapse. A few years ago a client referred me to a friend who needed some search engine optimization. The friend operates an adult website. Adult websites make a lot of money but have trouble finding honest, competent help. One job turned into another, and working with adult websites has become a thriving business for me. My problem is that nobody knows I do this. My wife thinks that I design websites for local companies. I don’t work with sites that do anything illegal or that produce “desperation porn.” My clients are high-end, soft-core sites. I’m getting to a point where I can’t hide this anymore. I’m going to get a prestigious industry award, which means that an Internet search of my name will reveal the nature of my business. I also have had to hide profits in a secret mutual fund, because I don’t think my wife would believe that I make that much from designing websites for florists. I’ve wanted to walk away for a while, but the money has gotten us a lifestyle that we struggled to have for years. My wife doesn’t have to work anymore, our house is paid off, we have a college fund for the kids. I feel like I’m stuck between disappointing my family by turning off the money pump or having them find out that I work in the adult entertainment industry. I need advice.

I did not watch Breaking Bad, so I don’t know if Walter White had your dilemma of receiving an award from the crystal meth manufacturers of America. Your immediate problem is easy to solve. You thank the heads of your industry for their generous recognition, then you inform them that for personal reasons you must decline the award and ask that your name be deleted from the event. Alternatively, you could say to your wife, “Hon, I’m being honored at a big industry award ceremony and I want you to come!” The evening would be revelatory for her, and you two would have plenty to talk about during the car ride home. This was the first I heard of “desperation porn,” the plot of which revolves around the (usually female, often clothed) star’s ultimately unsuccessful struggle to find a place to pee. I don’t understand your scruples about this harmless-sounding genre, and if others want to make beautiful urination movies, let them get showered with money. As for what you do for a living, I don’t see that it’s wrong or something to be ashamed of. You’re helping provide a service for which millions are grateful. The only true red flag in your letter is your hiding your profits from your wife. If you file a joint tax return and you aren’t declaring all your income, that sounds more compromising than your work. Maybe your wife is like Carmella Soprano—she knows but doesn’t want to know. Surely she realizes that the economy has not rebounded so dramatically that you’ve funded your kids’ college educations by showcasing the local florists’ special on clitoria. I think you should own up and tell your wife. Before she insists you quit, let her know that will mean she has to return to her job, and you’ll all be eating spaghetti for dinner for the foreseeable future. The kids only really need to know that dad makes his living as a Web designer (which is true, just as Tony Soprano really was in waste management). Regardless, your letter has just done a great service for struggling freelance Web developers everywhere—expect your competition to heat up. —Emily Yoffe

From: Help! My Family Has No Idea All Our Money Comes From Porn Sites. (Sept. 25, 2014)

Dear Prudence,

My wife of more than 10 years has always been a bit of a nudist. Nothing public, but around the house and our pool and out in the boat she likes to be in the buff. Our son is now 6 years old and my daughter is 3. My children are being raised in the nude, the same way my wife was raised. They get home from school and their clothes come off. I come home at night to two naked kids and a naked wife. Now that our children are getting older, I think it might be time that everyone starts covering up a bit more. My wife disagrees and does not want to change. Are we doing damage to our kids here?

I wonder if the mail carrier, just as a courtesy mind you, instead of pushing the mail through the slot, always makes sure to hand it to the lady of the house. You say your wife is a “bit of a nudist.” But from your description, I take this to mean that she reluctantly puts on clothes only when not doing so would get her arrested. I once hung out at a nudist colony for a Slate article, where I discovered I am most emphatically a “textilist.” After spending the day with a couple hundred naked people, I came to the conclusion that no one should take off their clothes, ever. (I also learned that gravity is a force that all must reckon with.) Your wife is a second-generation nudist and she is trying to turn her kids into a third. But it’s unfair to impose this on them. For one thing, if the clothes come off when the kids come home, that means no other playmates are allowed over. I learned at the colony that children raised to let it all hang out start wanting to cover it up once puberty hits. Surely, once your son refuses to let his naked mother wrestle him out of his clothes, he will also start wishing every time he looked at his mother he didn’t have a daily reminder of whence he came. I think a clothing-optional option is only fair for your children, as long as it is truly an option. But good luck convincing your wife that you’d like her to spend more money on her wardrobe. —EY

From: Help! My Always-Naked Wife Is Turning Our Children Into Little Nudists. (Nov. 20, 2014)

Dear Prudence,

I teach at a small liberal arts college where the work climate is fairly chill. There is a student who I have a teasing friendship with. He is not in my department, but he sometimes hangs out in my office and will occasionally join the group for lunch. It has recently been brought to my attention by a colleague that another faculty member has noticed and commented on the excessive amount of time I have been spending around this student. She (the colleague) advised me to separate myself from the student immediately, because the situation was bordering on inappropriate. (The student and I also happen to both be gay men—he is 19, and I am 40.) I’ve kind of had an “a-ha!” moment over this, and I realize now that I’ve gotten lax. Even the appearance of impropriety or favoritism can cause trouble, and I intend to simply end the behavior. My question is this: Should I explain any of this to the student? I am willing to just be cordially professional to him, but knowing I’m under scrutiny over this makes me not even want him in my office. Should I send him an email saying, “Hey, we can still be friends, just not at school?” And see, obviously that sounds creepy as hell too. Any advice?

What you’ve described sounds to me like a mostly innocent transgression (thus far), although I think you’re right to take your colleague’s advice and scale back without making any sort of announcement to the student in question. Part of your job is to model appropriate boundaries with students, and although you two can continue to banter during group lunches, I think you should focus on minimizing alone time and on making sure that you don’t turn your office hours into a social hour with students outside your department. If he stops by, you can let him know that your office hours are for students in your classes with questions about their work and that you’re not available to socialize. Presumably you can do so in a warm but clear tone, one that doesn’t make him feel berated for doing something you’ve allowed in the past, but that also makes it obvious that things can’t continue as they did. Practice the art of polite distancing that should be in the arsenal of every professional. —Danny M. Lavery

From: Help! A Colleague Told Me I Was Getting Too Friendly With a Student. (Oct. 4, 2016)

Dear Prudence,
I am pretty open-minded when it comes to sex and willing to give most things a go. My boyfriend of six months has a serious foot fetish and was over the moon when I told him I was game. I actually really like the foot rubs and my boyfriend’s treating me to pedicures, but the stilettos are killing me. I have a knee injury that makes anything other than flats send shooting pain up my spine after about 15 minutes. I am fine wearing high heels in the bedroom but my boyfriend keeps pushing at me to wear heels during all the various holiday events we have to go to. It hurts and kills my libido. My boyfriend has given me very expensive insoles and other gifts but it makes me feel worse. We actually fought over my wearing a pair of black ballet flats to his office party. We get along well on everything but this and I feel like an idiot for considering this issue above all a deal-breaker. Am I crazy? Not being a good, open-minded girlfriend?

Take off the stilettos and the boyfriend while you’re at it, my God. If you think you are a bad girlfriend for being unwilling to exacerbate your knee injury in order to keep your boyfriend’s arousal constant 24/7, then your standard for what constitutes a “good girlfriend” is impossibly, and unhealthily, high. There’s reasonable accommodation of a fetish—like wearing high heels during sex—but what your boyfriend is pressuring you to do is painful and seriously over-the-top. Ask yourself if you would ever expect him to do something repeatedly, for hours, that both “hurts and kills [his] libido” just because it turned you on. I’m guessing the answer is no. The ballet flats aren’t the deal-breaker; the deal-breaker is that your boyfriend seems perfectly content to put you through hours of pain and discomfort on a regular basis to satisfy a fetish you’ve already gone out of your way to accommodate. The deal-breaker is that he’s being inconsiderate and selfish, not that he’s into feet. —DL

From: Help! My Boyfriend’s High-Heel Fetish Is Killing Me. (Nov. 29, 2016)

From How to Do It

My boyfriend is, uh, huge. Long and thick as my wrist. We go slow and use lots of lube, but my vagina has a tendency to get really tight when I’m close to coming (and I’ll be close for like 10 minutes before it happens) and it leaves us both quite sore—though because of endorphins, I tend not to feel the pain until the next day. And we’re currently in that new-relationship period where we just want to screw nonstop as often as possible. I see sex tips about how to make a vagina feel tighter, but what should I do?