The Playboy Advisor

Q: Is it normal to think about sex 24/7? I’m a 28-year-old woman who just got her master’s degree and is playing the field while praying for a future partner—and I honestly feel that I’m addicted to sex. It just naturally seeps into my thoughts no matter what I’m doing, even at the most inappropriate times. When I envision my future partner, he’s just as much of a freak as I am! Are there other men and women out there who feel the same things?—T.G., Bangor, Maine

A: We are all so much alike! The details may vary, but the root questions are pretty much the same: Am I normal? Am I worthy of being loved? Based on what you describe, the answer to both those questions is “Hell yes!” But if you’re worried about your relationship with sex, ask yourself these questions: Is my sex drive in conflict with local laws? Has my sex drive blatantly impeded my progress in other areas of life? Is my sex drive often a point of moral contention in my relationships? If you answered yes to any of these, it might be a good idea to speak to a licensed professional—not because you’re an addict per se but because balance isn’t easy. If you answered no to all three, and you find that sex is by and large a joyful part of your life, just know that I’ve never met a single human being who claimed their sex life, libido, desires, opinions or beliefs were perfect. We are all trying to find love, make connections, grow, have some orgasms and make peace with ourselves (in no particular order). That said, there is absolutely a partner out there for you who can match your physical drive and meet your emotional qualifications; you just have to be intentional in finding him. As a woman who just completed her master’s, you already get the formula: Know who you are, know where you fit best and immerse yourself in that community so you can align with like minds in the areas that matter to you the most.

Q: I’m a man in his 30s and have been in a relationship with someone I deeply love for two years. I recently met another woman who’s cool and works in the same industry as I do. We got together for coffee a couple of weeks after meeting, and we’ve been texting ever since—maybe it’s just friendly, maybe it’s a little bit flirty. I still haven’t told her I have a girlfriend, and it’s starting to feel weird. On one hand, I don’t want to assume she likes me “that way.” On the other, I feel I’m being dishonest with her and especially with my girlfriend. Where do I go from here?—S.P., Arlington Heights, Illinois

A: First, know that scenarios like this will come up on both sides. I highly encourage you to discuss it with your partner, because at the end of the day, having a second person to navigate the complexities of life with is the joy of being in a relationship! Why is it that in romantic connections we accept that we have to share the undersides of our humanity (poop horror stories, credit drama, morning breath and all), but when it comes to our natural drive to desire and be desired by others, we all want our partners to believe we’re superhuman? Well, as it turns out, you’re not made of steel—so don’t be afraid to admit that to your girlfriend and ask for guidance on how to manage both the situation and your feelings. As for the other woman, you already know the answer to this: Yeah, you should bring it up, but I also think your senses are correct. Instead of making it a cautionary statement, look for a casual way to insert it into the conversation.

Q: I recently started dating a person who’s transitioning and has bottom dysmorphia. They were born with female parts, and as a female I thought I would be able to better figure out their body, but it’s daunting right now because they feel weird about their genitals, and I don’t know how to navigate. How can I get to know my partner and their body in a way that will make us both feel comfortable?—J.M., Miami, Florida

A: Congrats to your partner for making such an important decision, and also congrats to the two of you on your new connection. I’m going to remind you of something I’m certain you already know: Change is not easy, and it absolutely is not instant! Your partner may have spent 20-plus years feeling uncomfortable in their body or getting messages about their genitals that never aligned with their feelings—and as powerful as the decision to take ownership over their truth through transitioning is, it does not magically erase all those damaging, dysmorphic years. If it took them two decades to make the decision to change, they’re allowed to take at least a third of that time to heal from the dissonance they were surely feeling all that time. The good news is that though change isn’t instant, if nurtured, it can be gradual. Through patience, positive affirmation and lots of communication, you should see an improvement in their attitude toward themselves, which will result in a better connection in the bedroom. Just remember that you should not expect a 180. Allow them to take the lead as much as possible. If you need a nudge, watch porn that turns both of you on and use it as a tool to discuss what you’re comfortable and not comfortable exploring together.

Q: My girlfriend and I (a man) have been together for three years, and I love her immensely, but due to a lack of activity, our sex life is not that great. She works as an exotic dancer, and I think this affects her views on sexual intimacy. When I try to talk about it with her, she mainly tells me what I want to hear or avoids the question altogether. I would like to break down that barrier and get her to be more open. I know this will be difficult because of the industry she works in—and I have chosen to accept that aspect—so how can I help our sex life progress?—R.U., Philadelphia, Pennsylvania

A: With this attitude you’re already 80 percent there; all you have to do is figure out the other 20 percent together. I would imagine that, as an exotic dancer, your girlfriend might have some difficulty untangling her sexual practices at work from those at home. At work she probably has two modes: one in which she portrays someone else’s sexual fantasy and another in which she shuts down her sexuality to recenter herself. It sounds as though this mirrors how she treats conversations around intimacy, either saying what she thinks you want to hear or not speaking at all. My guess is she would like space to call the shots, to allow things to be her idea and to know that there is no expectation for anything other than her truth. This transition may take time and a lot of verbal affirmations along the way. As a starting point, I would suggest you learn her “turn-on triggers”—a system I created to help couples understand, beyond basic biological instigators, what gets their partner in the mood. The triggers are environmental (the five senses must be appeased, meaning the environment must be tidy and set), mental (e.g., a sapiosexual who requires a mental connection before a physical one), desire (direct language or actions that make someone feel wanted), cat-and-mouse (power play in which a partner likes to work for it or be worked for), negotiated (something else in addition to sex must be offered to sweeten the pot) and visual (attention to appearance is paramount). I have a quiz you both can take to learn what each other’s triggers are: thegameofdesire.com/quiz. Try it out as a launching point.

The woman who has never had an orgasm or masturbated has likely not found her middle, because no one has ever invited her there.

Q: What advice would you give a 20-something woman who has never had an orgasm because she can’t rid herself of the idea that self-pleasure is bad or dirty? She doesn’t know what she likes or even how to figure it out, which makes telling her partners what to do that much more difficult.—R.W., Toronto, Ontario

A: I have seen this question many, many times. What that person needs more than anything else right now is patience with herself as opposed to a quick “get over it and get into it” fix. Years and years of sex-negative messaging are not that easy to erase! I am a person who has drenched herself in sex-positive content, and I still, at times, feel internally shamed. Instead of trying to ignore those feelings when they come up, I embrace them. I examine where they’re coming from, I ask myself how credible the original source is, and I make tiny adjustments to my behavior so that I can work through my feelings—slowly. The woman who has never had an orgasm or masturbated has likely not found her middle, because no one has ever invited her there. Her past told her to deny her sexual self, and perhaps those in her present are pushing her to be totally liberated in her sexual pursuits. That’s a big jump. I would suggest she ignore both, find her own true starting point and take it from there. And because this can never be said enough, I’d like to add that while it can seem as though the rest of the world is living in the land of milk and orgasms, women’s pleasure researcher Elisabeth Lloyd, author of The Case of the Female Orgasm, has found that only 25 percent of women are consistently orgasmic during vaginal intercourse and about five percent never have orgasms. The path to pleasure is not linear for many women—all the more reason to take it slow and do it your way.

Q: I’m in a monogamous relationship with the love of my life, but I’ve recently become attracted to someone else—a woman (like me)—whom I know well and have been interested in on and off since before this relationship. I’ve suggested polyamory, but my partner isn’t onboard with that. What should I do?—G.S., Sausalito, California

A: It sounds like what you need is an opportunity to explore this connection with your “someone else” without impinging on your primary partnership. Interest and engagement are very different things. After spending more time with the other woman, the reasons the two of you never worked out may become clearer. On the flip side, maybe through this exploration you’ll decide that she can actually improve all your relationships by allowing you to be in full, balanced expression. At that point I’d revisit the polyamory discussion with your partner. You may be looking for a free relationship—defined not by the rules or titles you chose in the beginning but by how each partner feels at any given time. The only thing constant in this world is change, and in a free relationship this isn’t just your reality; it’s your mantra. In order for this arrangement to thrive, you must be committed to hearing your partner’s truths without constantly personalizing them. You acknowledge that your relationship is yours to experience, not to control. In short, when it comes to the rules of your relationship, you edit them often. And I suspect that right now what you need is a relationship that gives you space to flirt, connect and gain clarity.

Q: I want to get straight to the point: How do I get women to like me? I’m a 28-year-old black male who’s never been in a serious relationship or had vaginal intercourse. (I once paid a stripper to let me go down on her, but that’s it.) I’ve tried dating apps and shooting my shot on Twitter, but I still get nothing. Am I doing something wrong? Am I just ugly? Am I doomed to a life of watching porn all the time and paying strippers?—P.S., Atlanta, Georgia

A: I am so grateful for this question. It is vulnerable, authentic and relatable. And you are already on track to solve your dilemma, so all I’m going to do is point that awesome energy toward some action. I have a five-phase strategy you can use to make yourself a masterful connector. Here’s the lightning-round version:

1. Get to know yourself. This does not mean take yourself on a long romantic walk; it means start identifying the core of who you are and how you tend to interact with others. I suggest doing the Big Five Personality Test and an attachment-theory quiz to start. Invest some time in studying emotional intelligence to help you master your interpersonal life. Next, take what you’ve learned and get feedback from others; after all, the mirror cannot see itself. Since you don’t have an ex, ask a close friend or family member how you can improve as a connector, and if you sense they’re giving you answers to support your ego versus your growth, tell them you can handle the truth—and you need it in order to move forward.

2. Change yourself. Those are triggering words, I know, but change is the only constant; all you’re doing is taking ownership over the process. Based on what you’ve learned through your self-assessment, start making small intentional changes so that who you know yourself to be and how people perceive you are more aligned.

3. Learn from the greats. Once you’ve gotten good with you, start reading books or enlisting the help of experts to learn how to attract others. We’re told that flirting, seduction, social intelligence, charisma, empathy, humor, strength and even attractiveness are traits we’re simply born with, but in truth these are all skills that can be taught.

4. Practice, practice, practice. There’s a reason pro athletes practice more than they play: If you can’t do something when the stakes are low, you won’t have a chance in hell of performing when pressure, nerves and clocks are in the mix. So learn to love socializing, start conversations with no agendas and be charming to everyone you meet. Not only will this make you a better dater; it will make your time on this planet more pleasant. 5. Set yourself up for success. Now that you’re good with you and good with others, put yourself in environments that welcome, want and warrant the absolute best version of you.