This Is Supposed to Be Fun

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Who Are You and What the Hell Are You Doing Here?!

If I didn’t define myself for myself, I would be crunched into other people’s fantasies for me and eaten alive.

—AUDRE LORDE

Knowing who you are is hard work that literally takes a lifetime. Most of my coaching clients have done some work to understand who they are, but they have still found it challenging to hold on to their truths as they navigate relationships and sex. That’s because most of us aren’t encouraged to ask ourselves important questions about who we want to be as romantic partners and what relationship we want to have with sex throughout these partnerships. And what we want from relationships often depends on other areas of our lives—like career, health, and family—that change as we change. The kind of relationship we gravitate toward in our youth might not work with the demands of our later career goals. The need to be present for a sick parent or friend might alter the way we view what’s important in a long-term partnership. Even learning more about what and who you like through the process of dating can dramatically shift what you believe you want when it comes to sex and partnership. It can be daunting to start the process of digging into who we are and prioritizing our sex and dating lives. But that’s exactly what you’re here to do—with me as your helpful guide, of course.

My hope is that by reading what I have to offer you in the chapters that follow and taking an active role in your own learning, you’ll gain insight into yourself as you are now. This insight is the key to dating with confidence. The more you know yourself—why you believe what you do about the world and what you want from it—the more you’ll be able to share that with others. And isn’t that essentially what dating boils down to, sharing yourself with others and connecting with what they have to share with you?

You have a past that brought you to your current dating moment. You may understand and accept that past already, or you may need to unearth some buried history that, for better or worse, has been shaping your present dating life. Knowing where you come from and what messages you inherited about sex, dating, partnership, marriage, and family are the first steps to truly knowing who you are as a dater. When you meet prospective partners, you bring your ideas of how things should be into your dance of conversation and flirtation, and so do they. The thing is, most of us rarely question if what we’re bringing to this dance is actually in our best interest. That’s why it’s such a good idea to do some introspection, to see if your expectations align with your current dating reality.

This chapter is all about exploring you. We’ll dig into your past, bring to light how it may be impacting your current dating situation, and put these pieces together to form who you are as a dater right now. You’re going to have lots of opportunities to explore your thoughts about dating, from what kind of relationships you ideally want to how masturbation fits into your dating life.

If you’re excited, nervous, or a mix of both, that’s okay! Take a moment to think about anything that is coming up for you now. It will be great to reflect back on these feelings later to see how you’ve changed.

KNOW YOUR HISTORY

How would you describe your upbringing in one sentence?

When forced to condense family history into a single thought, most people will comment on a few key factors that influenced how they were raised. It’s common for folks to invoke descriptors of race, ethnicity, socioeconomic status or class, religion, and other cultural affiliations. These same descriptors can be used to examine how we developed our ideas about relationships, because our families are the proto-relationships we grow to understand and replicate.

You may have grown up with some pretty strong ideas about how romantic relationships work. You may have had religious or spiritual teachings that dictated when sexual contact could and couldn’t happen, and you may have parents or close family members whose relationships seem to have followed along with these edicts. For you, it might feel like there is really only one path to relationship happiness. Or, you may have rebelled against these ideals to pave your own way.

For those who grew up with examples of different types of relationship structures and expectations within your family, you may have seen so many ways to be in relationships that you internalized that making your own relationship rules was totally okay. You might sometimes feel overwhelmed by choices and unsure about which relationship structure could work for you. You may have even opted out of dating because there weren’t any clear relationship success stories to hang on to on the bumpy path of your own dating life.

It’s worth noting that many of us grew up with cisgender, heteronormative, monogamous examples of relationships that simply don’t seem applicable to our own romantic and sexual development. This is especially true for LGBTQIA+ and polyamorous folks. The examples we get aren’t always the ones we need.

Take Tasha, for instance. She was a client of mine who experienced major shifts in her thinking about her dating life when she started looking at her history. Each of my clients completes a sexual history and assessment before our first session together. Sometimes clients are eager to fill everything out and send in their responses. Others wait until the very last minute. Tasha was in the latter camp; she actually sent in her assessment minutes before her first appointment. I began that session by asking her what the process of reflecting on her sexual history was like for her, and she said it was more difficult than she thought it would be.

“I realize now that the thought of answering the questions in the assessment gave me a lot of anxiety, so I kept putting it off and putting it off. I knew I had to turn something in today so I just made myself do it. It was hard to reflect on how isolated I felt growing up. Being queer, I couldn’t relate to any of my family. I was learning who I was attracted to, but I didn’t have anyone to share that with. My sexuality felt dangerous, like something I had to protect other people from. Having to reflect on that, and think about how that impacts me now… It was really hard.”

“Do you think that feeling of isolation has been impacting how you date as an adult?” I asked her.

“Maybe. I know so many people now who seem to have the life I want. They seem more confident in what they want and more adventurous when it comes to dating and hooking up. I tell my friends all the time how jealous I am that they seem to actually be having fun out there and I just feel stuck.”

During the course of our work together, Tasha was able to create a vision for her future relationships based on a partnership model she believed was right for her. This model was inspired by what she found herself envying in her friends’ relationships. She wanted commitment ultimately, but she also wanted fun and excitement and to feel like the people she was dating really saw and accepted her. This meant that she focused her search on people who were a little farther along in their own sexual and coming-out journeys, who could show her what was possible. By recognizing that she needed a different model from the one she had initially been given, she found the freedom and ability to seek out partners who helped her learn more and enjoy the process of dating.

Sometimes family provides just what we need. You may be someone who wants what your parents have, and that’s great! I’ve had many clients whose major source of dating frustration was trying to find the kind of partnership that their parents or other important elders in their life have. We work together to make sure they are crystal clear about the relationship qualities they’re looking to emulate, and then build these things into their dating profile and vetting process. You’ll learn later on how to do this too!

There’s no right or wrong when it comes to how we do our relationships. Whether or not you have a vivid picture of what you want your future relationship(s) to look like, just know that there are others out there like you who are trying to figure out who they are, find their person or people, and have a good time in the process.

GETTING PERSONAL

There’s not a ton of space in life to think about the childhood messages we received about relationships, so I’m creating that space for you right here.

Let’s start with a few questions about you.

Now that you’ve thought through some of the ways that your upbringing has impacted how you feel about relationships, let’s move on to how it might affect how you feel about sex.

NORMALIZING S-E-X

What messages about sex did you receive when you were growing up?

If you are like most people, you probably received conflicting messages that you’re still trying to understand. Alongside the influence of our family, the culture we grow up in plays a big part in how we think and feel about sex. Every other pop song is about it, and we consume a ton of other media containing it, but just try talking about sex with other people (let alone a potential partner)! It can sometimes feel as if sex is simultaneously everywhere and nowhere at all. Like it’s something we’re supposed to want desperately but at the same time stress out about or even avoid. While most of us have a general belief that sex is a natural part of life, there’s often much more to it than that.

Despite depictions of sexuality being everywhere, we actually live in a sex-negative culture. Despite our best efforts, we all have absorbed some form of sex negativity. The inability to feel comfortable voicing desires or talking openly about sex with people we trust points to a stigma that still exists: sex is to be done, not discussed. Yet the majority of my clients, whether single or partnered, list a lack of good sexual communication as one of the biggest obstacles in their relationships.

There is nothing inherently wrong or bad about having a sexual experience with someone (or many someones), but so often our culture reflects only the negative consequences of being sexual. This can lead to internalizing our desires and can create feelings of shame for wanting to be sexual, even when the conditions feel right for us. And if you identify as asexual, there is very little space in our culture to talk about what that might look like in relationships. There’s an inherent sexualization to dating that might feel off-putting if that’s not your main motivation for seeking connection. So whether sex is desired or not, you can be left feeling ashamed for wanting what you want.

If you are looking to have sex as a component of your dating experience, and you’ve never thought about what is right for you, here are a few common questions I am frequently asked to help you get started.

Chances are you have answers to some if not all of the above questions. But are these your answers? Are they conclusions you have come to because of your own experiences? Or are these answers you have absorbed from your upbringing or culture? Do these answers feel right for you now?

In my professional opinion, the answer to all of these questions is “It depends.” So much of how we experience, process, and enjoy sexual relationships depends on what we think about sex. That’s why, regardless of how you answered, there is a lot to learn about why you think the way you do about sex. You may know people who don’t adhere to or reflect the answers you just provided. Do you have judgments of them? It’s worth exploring how your beliefs differ from those of people around you and even, if it feels comfortable, talking openly with them about their beliefs and how they came to them. Sex often feels like an off-limits subject because we’re not sure how other people feel about it, but that’s actually a great place to start the conversation.

Knowing your own beliefs about sex and how you came to them can be extremely helpful in your search for partners. Having this knowledge will help you communicate yourself and your desires more effectively throughout the dating process. For instance, if you believe that having sex on a first date is not okay, and you are faced with the option to do so, it will be helpful for you to know why you believe this so you can make a decision based on what you need and desire in the moment.

TO HOOK UP OR NOT TO HOOK UP?

We all live with a tremendous amount of cultural pressure to keep things casual in dating. Millions of people use dating apps that have a reputation for facilitating easy hookups. The concept is so widespread, it sometimes feels like hooking up and dating are one and the same. They’re not! Hooking up is a part of dating that you can choose to engage in or not.

If you have a strong belief that casual sex is wrong, then you may have resisted hookup culture. But if you’re anything like my client Sierra, you may have dipped a toe or two into the hookup pool.

Sierra came to me looking for guidance through the wild world of online dating. A recent grad, she told me that she was ready to look for something serious. All throughout college, she had limited her relationships to a hookup here and there while she focused on her studies. She also had an extensive calendar of extracurriculars, so there just wasn’t any time for more than the occasional sex sesh. She was okay with this as a means to a sexual end, but now she was ready for more, and it was proving difficult.

After moving cross-country for an amazing job opportunity, Sierra found herself in an unfamiliar situation: she no longer had a community of friends to introduce her to potential partners, and she was floundering between one-night stands and having to actually go on dates… sometimes in the light of day! Then she said something I hear time and time again: “I just don’t know what to do, or what to say. This is all very new to me, and I just feel like I’m really bad at it.”

Sierra, like so many of my clients, grew up hearing messages about her education being the most important thing, while romantic relationships were potential impediments to her success. It was just easier, and culturally expected, to keep relationships in the hookup zone. I have seen this across the gender spectrum and in folks who identify as all different orientations. Hooking up is often seen as a way to let off some sexual steam (and it definitely can be!), but folks who hook up exclusively can struggle with a lack of practical dating skills—skills that Sierra was realizing she desperately needed now.

In our work together, Sierra shared that she was raised by a single mom most of her life. Her stepdad, who married her mom when Sierra was in high school, was an amazing human. She loved seeing her mom in love. When she thought about what partnership meant to her when she was younger, it was hard to admit, but she didn’t value it much. She saw that her mom was happy, for the most part, being single and taking care of her. It naturally became important for Sierra to create a life for herself that felt similarly independent. A lot of our work focused on whether those childhood feelings were still valid. Some of them were. She wanted to be self-sufficient and autonomous, but she also craved a partner with whom she could share her wins and losses.

“I’m not someone who needs a partner. I actually love doing things on my own. But at the end of a long week, it would be nice to have someone to spend time with who really knows me,” she explained.

“And you haven’t had that experience so far with dating?” I asked.

“Not yet! Every time I meet someone, it always seems to result in a one-night thing, or it’s casual for a few months and then peters out. It’s exhausting starting from scratch every few months.”

The more we talked, the more it became clear that she wanted out of the hookup loop—it just wasn’t delivering what she needed anymore. Though it had served her needs in the past, she was learning about who she was becoming and what she wanted in her future. We worked on refining how she could express what she wanted from dating in her profile, expanding her practical experience going on dates, and reflecting on whether the folks she was meeting aligned with these new desires.

At the opposite end of the spectrum, my client Keaton needed a gentle nudge into the hookup pool. While he had been in two major long-term relationships, he was beginning to wonder whether his gauge for good partnerships was a bit off. His relationships always fizzled out sexually. He described both exes as being “really great friends,” but the chemistry had never been that strong to begin with.

His sexual history involved becoming intimate only when he was in a committed relationship, and he had often felt that he couldn’t fully express himself sexually with his past partners. In truth, he didn’t exactly know what he was looking for; he just knew that what he was doing wasn’t working. He had recently been on a string of dates with women who expressed their sexual interest in him early on, and he had frozen on the spot. His tendency was to take his time, establish a friendship, and then move that relationship into sexual territory. He knew that hooking up was an option; he just wasn’t sure how he felt about it. Would it make him a bad person? Would he be taking advantage of someone? We talked about his upbringing and how sex was never really discussed except when mentioned in the context of marriage. He obviously wasn’t waiting until marriage to have sex, but in the past he had experienced a lot of guilt when even considering a casual encounter. He realized that he had internalized the message that sex should only happen when there’s some form of commitment.

After a while, Keaton was able to separate himself from the expectations of his family and realize that he was already on a different path. Why not push his boundaries a bit? One day, he began our session with “I did it!” and explained that he had had an amazing night with a woman who was passing through town for work. He was elated by his experience with her, stating that he had never felt that kind of intense sexual connection. They had hit it off on their first date, which became a twelve-hour-long dinner turned overnight experience.

“Are you feeling any guilt?” I asked.

“A little… but the pleasure of having such a strong sexual connection exceeds any guilty feelings. I’ve never connected with someone like that before. I always thought I was just more sexually reserved than everybody else, but I noticed myself letting go a bit more because I wasn’t hung up on where this was going to go. The fact that she was leaving town meant that it was kind of now or never, and that was the push I needed to just go with the flow. I wasn’t 100 percent sure we were going to have sex; I was just enjoying each moment.”

“That’s great! You learned what your sexual connection could be when you’re less attached to the outcome of the relationship. That’s huge! Think you’ll do this again?”

Keaton paused. “I don’t know, but I’m definitely more open to possibilities now!”

EXERCISE: CREATING A HOOKUP PROS AND CONS LIST

As with anything in life, you have to evaluate what you think is right when it comes to dating by weighing the pros and cons. What do you want to focus on right now? Gathering sexual experiences with no strings attached, connecting with other people who are interested in more, or both? There’s no wrong answer, just arguments for and against based on what you feel will work best for you right now. Relationships can provide stability when they’re with great matches, but feeling stuck with someone who drains your energy might be a huge setback. Hooking up to learn about yourself and what you like can be super fun, but what about when someone is a jerk or you find yourself wanting to keep things casual with someone who catches feelings for you?

I encourage you to create your own personal list of pros and cons for hooking up and relationships. Remember, this is an exercise for who you are now. Your past self may have thought differently, and you may look back on this in the future and think, “Wow! I’ve changed a lot.” What matters is that you’re getting to know how you feel about these types of situations as the person you are right now. Making a pros and cons list will allow you to tap into what makes sense for your life given your past experiences and your current beliefs and needs. That’s how you start to build dating goals for the future!

THE GREATEST LOVE OF ALL

Now that you know how normal it can be to use dating as a way to learn about yourself and that hooking up is one of the many reasons people choose to date, it’s time we talk about an often overlooked part of the dating process: masturbating. Why am I bringing masturbation up, and so soon? Because I frequently hear from my dating clients that they want to have healthy and fulfilling sex lives, but they never learned to self-pleasure and struggle with communicating what they like. Developing a masturbation practice is my primary recommendation to those clients who feel at a loss when it comes to knowing and describing what they want. Some of my clients are in partnerships with mismatched libidos, and they tell me that they masturbated more frequently when they were single. Now that they have a partner, they’ve thrown all their eggs into one sex basket—to disastrous effect. Masturbation is a great way for folks to take ownership of their own desires and balance the responsibility of satisfying those desires within a partnership. Whether you are single or partnered, masturbation can be a great outlet for expressing sexual desire. For these reasons, I encourage everyone to cultivate a masturbation practice that can be relied upon through thick and thin.

You are your first and longest-lasting sexual partner. Think about it: most of us start self-pleasuring at a very young age. Your gender, culture, and upbringing will have influenced how you felt about it at the time, or even now, but the fact remains that, from early on, you do you! A lot of people think that masturbation is something to be ashamed of and grown out of, and that the goal of dating is to eradicate the need for this unseemly activity. This just isn’t the case. Another person isn’t responsible for fulfilling all of your sexual needs. And they shouldn’t be asked to, since you already have a reliable sexual outlet in yourself.

Using solo sex as a way to maintain your own erotic energy is a fantastic, safe, and pleasurable practice. We have bodies that desire pleasure, and in the absence of sexual partners we can give that pleasure to ourselves. It’s quite empowering when you think about it. Cultivating a masturbation practice means that you recognize your sexual desire when it arises and tend to it. In other words, masturbation is a road map for getting from sexual frustration to sexual fulfillment all on your own.

We can also use masturbation as a way to explore how our bodies respond to sexual stimulation. One of the first things I discuss with my clients who struggle with getting what they want from partnered sex is masturbation. Most of us have ways that we enjoy receiving pleasure, no matter who is doing the touching. Knowing your own body and what it likes is crucial to having the best sex possible, because if you don’t know how to please yourself, how can you show someone else how to please you? Knowing what turns you on and being super familiar with your own body makes communicating your needs much easier.

CREATING A SELF-PLEASURE RITUAL

Centering your own pleasure can be a fun and sexually rewarding experience—a gift you can give yourself whenever you need it. You may have some intense feelings about masturbation, so if that’s the case, please take a moment to reflect on what feelings are coming up for you.

What associations do you have with masturbation? If you’re new to it, how might you start to use it as a tool for exploring your body and desires? If you are already fairly comfortable with masturbation, how might you use it more consistently to support yourself throughout dating? Now, think about how you can extend your self-care to include self-pleasure. What would that look and feel like?