The Playboy Advisor

Q: How many women watch porn and masturbate with their boyfriends? Online sex therapists seem to routinely advocate this practice, but I haven’t met a single woman who actually engages in it. Here’s my story: My boyfriend and I have a healthy sex life, but he admits that he masturbates to relieve stress. He loves porn, and he says he never looks at photos of me when he’s flying solo because he doesn’t want our intimacy to be “superficial.” I’m already insecure about my body, and I know I’ll never live up to the women he’s watching. I’m not a big fan of porn, nor do I need to masturbate when I’m in a relationship. Should I let him continue to do his thing, vocalize my insecurity or suggest mutual masturbation (and possibly humiliate myself in the process)?

—E.V., London, U.K.

A: Let’s begin by acknowledging the utility of porn. Pornography is consumed largely as a stimulant for getting off—not, as you seem to fear, as a substitute for sex or as a standard of attractiveness. Couples may choose to watch porn together to set the mood. Some masturbate while watching it, others don’t. Some watch together because they find it titillating, others because it’s intriguing, and the rest do it because it’s funny.

In short, regardless of your relationship status, there are many reasons to watch porn. One thing is certain, though: Women absolutely partake alongside their boyfriends. Based on my research, few comprehensive surveys on this subject have been published, but with nearly 100 million people visiting Pornhub every day, it would not be unreasonable to assume that some of those visitors are couples in healthy relationships.

You should be grateful that your boyfriend is so forthcoming about his porn- viewing habits; he’s essentially handing you his unlocked iPhone. His relationship with porn and masturbation, as you describe it, seems to be a non-threatening one, given how he views them as separate from intercourse even though they’re just as integral to his emotional well-being. By the way, science is on his side: The mental-health benefits of masturbation include reduced stress, better-quality sleep and improved concentration.

You, on the other hand, seem to have a more, let’s say nuanced, relationship with masturbation, porn, sex and self-esteem. It’s important to be open with your partner about your insecurities—physical, emotional and sexual—because he who loves you may be able to help you overcome them. Forcing him into your comfort zone by giving him an ultimatum isn’t the answer. Nor should you suggest mutual masturbation if you’re not legitimately curious about it. (He may not even be interested, because, as you suggest, he likes to compartmentalize.) Sexuality is complicated, and even when we have romantic partners, it can be beneficial to experience some of our sexual desires and fantasies alone.

To reinforce why you needn’t worry about his habits, allow me to deploy the only kind of metaphor that can compete with sex: food. Sometimes you want nothing more than to slowly savor a succulent 10-ounce Wagyu filet mignon and a glass of cabernet. Other times all you crave is a cold slice of day-old Domino’s pizza. In both cases, you’re experiencing hunger; your means of satiation are merely circumstantial. Have confidence in knowing that pepperoni could never replace steak—and men love steak.

Q: Technology has created so many ways you can be caught juggling your options: random numbers texting you, aflame calling while you’re on another date, women messaging you in the middle of the night, Bumble notifications popping up unexpectedly, people adding you to their Instagram stories without permission. What’s the key to being on the grid while dating multiple people?

—J.S., Rockford, Illinois

A: Believe it or not, dating in 2019 is not that difficult. Turn on your phone’s “do not disturb” function before your date begins. In reality, the only people who fear being caught dating other people are those who are being deceitful, so your question seems to indicate you want to date in secret. That, my friend, is a zero-sum game in the digital age. Be up-front about your goals with everybody you’re dating. Anything else is a waste of your time and theirs. If you just want to have fun, let them know. If you’re not ready to be exclusive, let them know. If you have no interest in something long-term, make that clear before having sex.

At this point, most well-adjusted single people expect any social encounter to be interrupted by some form of technology. If you silence all your devices, your date will likely consider it chivalrous and refreshing. By the way, if you’re on a first, second or even third date and she demands to know why other women are contacting you, run.

Q: What’s the longest you can go without having sex with your girlfriend before you should worry about the health of your relationship?

—R.W., Idaho Falls, Idaho

A: What you’re actually asking is: Is sex a barometer for the strength of a relationship? The answer is no. There’s no universal timeline that tracks when a sexless relationship enters the “Holy shit, we’re in danger” zone.

Here’s the rub: Isn’t the guarantee of sex what makes committed relationships so fantastic? Of course it is! Even so, I wouldn’t dare suggest that a sexless relationship is an unhealthy one. Libidos ebb and flow. Stress, pregnancy, mother-hood, medication and menstrual cycles all have an effect on a woman’s sex drive. You should be sensitive to any of these factors, should they apply.

Because you’re asking, I assume you’re already concerned. Is your girlfriend aware that you’re concerned? Does she know your definition of a “healthy” sex life? My advice is to seduce your girlfriend to the best of your ability based on what you know turns her on. Should she demur, it’s time to have a dialogue about each others’ expectations in the bedroom lest you start looking elsewhere to fulfill your very human needs.

Q: If I had to make one luxury purchase to impress women, what should it be: a newer car, an expensive TV, a sophisticated wardrobe? I’m middle-income but want to own something that will wow every girl who meets me—something that proves I have class.

—B.C., Seattle, Washington

A: You’re reading PLAYBOY, so I assume you already understand that class is defined by attitude, not material goods. How you treat other women, the way you interact with waitstaff and how you talk about your exes and family will woo any well-adjusted woman more than Maseratis or Maison Margiela.

If you want to start presenting yourself to the world as a sophisticated man, how- ever, start with a smart wardrobe, which needn’t be astronomically expensive but should be an investment—in both time and money. As Will Noguchi, senior visual stylist of men’s subscription service Bombfell, advises, “You need to shop smart. This means spending your money on key pieces rather than a wide range of fast-fashion items.” He suggests starting with a fitted navy blazer, a classic leather jacket and a pair of dark-wash jeans. Jeans and leather jackets never go out of style; spend some extra money here as these pieces can be worn year-round.

“Aside from versatility,” adds Noguchi, “the most important thing to consider when updating your wardrobe is fit. Look for pieces with tailored or tapered fits to alleviate looking boxy. A ‘trim’ aesthetic will naturally give you a more expensive, elevated look.”

Q: I have been in a relationship for three years, and I recently played a joke on my boyfriend that I now regret. At Christmas, in front of my whole family, I got down on one knee while holding a small box and pretended I was proposing to him. (In reality the box contained a small gift for my mom.) My boyfriend, caught off-guard, looked panicked—a reaction I didn’t expect. We eventually laughed the whole thing off, but I haven’t been able to get the desperate look on his face out of my head. I can’t help thinking that he’ll never want to marry me someday, in which case what’s the point of prolonging our relationship?

—S.M., Cambridge, Massachusetts

A: You had it coming. Do you recognize that? Say it with me now: “I recognize I made a mistake. I do.” Good.

Marriage proposals are nothing to joke about, so consider your turmoil a referendum not only on your sense of humor but on your knowledge of your boyfriend’s headspace. I must assume he appeared panicked because you two haven’t talked about your future together.

Sit him down and have a conversation about where he sees this going. The two of you have been together for three years; at this juncture, talks of marriage and a proposal should be met with elation— that is, if a life of monogamy is what you both aspire to. Pick a time and place that will allow him to give you his full attention. Don’t do it before bed or shout at him from the kitchen while he’s watching TV. Get to the point: “Where do you see us in two years? Can you imagine us getting married?” Until you talk to him about his plans for your future, you’ll continue to worry yourself with speculation.

One of my more infamous dating stories involves spotting a hotter guy across the bar while I was on a date, faking a headache to end said date and then going back to the bar to pick up the hottie.

Q: I’m having a hard time sustaining a relationship because I love the chase. I don’t go out to bars with men I’m dating because my eyes wander. I recently stopped drinking because I recognized that, for me, getting drunk was synonymous with picking up men and having drunk sex with strangers. This is a pattern. (By the way, it was easy for me to stop drinking, so I don’t think I’m an alcoholic.) Do I need to give myself more time to sow my oats, or might I have an intimacy or commitment problem?

—R.G., Miami Beach, Florida

A: Oh, younger self, is that you? One of my more infamous dating stories involves spotting a hotter guy across the bar while I was on a date, faking a headache to end said date and then going back to the bar to pick up the hottie. The question is, Do you consider me talented or unstable?

For me, the chase was a means of avoiding one very real issue. Yes, I was afraid of intimacy, but I was terrified of rejection. When you’re constantly looking for the next best thing, there’s no way the person sitting across from you can hurt you. This is probably, at least to some extent, why you keep swiping left on men in real life. The thrill of catch and release insulates you from some harsher reality that no sex columnist should attempt to diagnose.

You may not have a drinking problem, but you most certainly have an intimacy problem. I was able to deal with my vulnerability issues through therapy; you might benefit from the same. An even harsher reality check is that for many people who exhibit these pat- terns, sooner or later their options run out. Don’t rob yourself of the gift of get- ting to know a sexual partner on a deeper level. Fleeting sex, one-night stands, free drinks and first-kiss thrills can sustain you only for so long. I would hate to see what happens should you ever find your- self alone at last call.

Q: I suffer from vulvar vestibulodynia and struggle with intense pain during penetrative sex. I’ve been going to physical therapy for a couple of years. I also take duloxetine, which helps control nerve pain, and my condition is slowly improving. I have a long-term partner who is empathetic and concerned about hurting me, so we’ve been relying almost entirely on clitoral stimulation. I’m ready to try penetration again but have residual anxiety from a lifetime of pelvic-floor dysfunction. How can I ease back into vaginal sex and shift my focus from pain to pleasure?

—E.S., Malibu, California

A: Vulvar vestibulodynia, a form of vulvodynia, is more common than you might think. It has been reported that up to 16 percent of women in the U.S. will experience vulvodynia in their lifetimes. And yet, most women who suffer from this condition do so in silence. It’s understandable that you have anxiety around potential pain, and you’re lucky to have a supportive partner. He’s going to be an important part of reducing your anxiety around sex.

Aside from being forthcoming about any anxiety you or your partner may have, come up with a safe word. Make it something non-pain-related and easy to say and remember. Agree that either of you is allowed to use it if sex gets too painful or if your anxiety starts to spin out of control.

Sex is a form of pleasure, and pleasure takes work and communication, whether you suffer from vulvodynia or not. Every healthy sexual experience begins with a clear mind that’s ready to focus on having fun, giving back and letting go. You’re lucky to have an amazing partner who seems to want to prioritize your pleasure. Be open to the journey.