Embracing Newbiehood: How to Approach Dating and Sex in Your 20s With Little or No Experience

It can feel like the world will end if you haven’t had sex⁠ or a sexual⁠ or romantic⁠ relationship⁠ by your mid-twenties. There are countless ways in which our culture puts pressure on young people to gain experience in romantic and sexual relationships. But truthfully, if you don’t have much, or even any, experience with dating and sex, you are not doomed to never experience romantic and sexual connection.

The world also will not end.

Everyone has a different history with dating and sex. You probably know someone who has consistently been in relationships since middle school. Other people go through their teens and even twenties without partners or without having sex. Of course, there's a whole spectrum of experiences in between. No matter our experience with dating and sex, we all pick up messages about how we should and should not be connecting to other people through our peers, families, educational institutions, and the entertainment industry.

We see our peers start to date and we use them as a benchmark to which we compare other relationships. From a young age we're bombarded with movies and T.V. shows about high school and college romance and hookups. We may look at our parents’ relationship to begin understanding the ways their dynamic indelibly influences how we connect to other people. It is also through other people and media that we pick up on which types of people are generally found or presented as attractive – in predominant Western culture, that's typically thin, abled, white, cis and straight. All of these messages add up. They tell us you need a partner⁠ or a sex life in order to be mature and fulfilled. At the same time, they tell us some people are more deserving of love and desire⁠ than others, making you feel like it is because of your own personal failure that you feel unlovable.

Feeling behind is not a sign of inadequacy, but an aggregate of unavoidable societal messages. When we can start to acknowledge that we all have internalized messages that don’t have our best interest in mind, we can hopefully also start to understand that feeling behind is not our fault.

But even when you know all of that? You might still feel anxious about being new to these experiences and relationships, or feel ashamed about feeling behind compared to your peers.

If you're first starting to approach dating and/or sex, you really do have some exciting opportunities to build trust within yourself and experience pleasure while being vulnerable to new experiences. Although being vulnerable like this is scary, newness has its benefits. In Buddhism, beginner’s mind is an ideal state, one where you are not yet stuck with opinions and certainties and can explore with curiosity. In the musician Robyn’s song, “Indestructible,” she's experienced heartbreak, but she pledges to come into her new love as if she’s “never been hurt before.” This kind of newness can be a real gift!

The Only Way Out Is Through
First, why not go ahead and just let yourself feel however you feel. Even if you understand that you feel “behind” about coming to dating or sex later than some because of cultural messages, that might not make you feel any differently.

Emotions aren’t rational, and we often can’t think our way around them. I want to give you permission to feel what you feel, to experience your feeling and let the emotions pass through you. See if you can get specific about what is coming up for you. For example, you may feel sad or anxious, but I am inviting you to go deeper.

Earlier this year, I realized I felt sad and pinpointed that I was actually feeling lonely. Even though I couldn’t make a romantic partner appear out⁠ of thin air, I took that loneliness and used it to intentionally get closer to my roommates, while holding space for romantic connection if it happens. Feeling your feelings is a lifelong process and practice, so no worries if you can’t get specific right away. I want to congratulate you for sitting with how you feel, for honoring your emotional world. This is important information. I want you to value it.

Getting clear about my emotions helps me respect, love, and take care of myself. I'm a trans girl, but before I started to think about gender⁠ , I identified as a queer⁠ guy in high school. During this time I felt lonely, which I realized was a combination of having almost zero dating prospects in my high school and internalizing my lack of romantic and sexual experience as me being unattractive.

Years later, even after having positive intimate relationships, I still feel tinges of doubt about if I’m "experienced enough.” When I feel a desire to hook up with someone, I ask myself if I’m approaching sex from a place of scarcity or a place of abundance.

When I’m coming from a place of scarcity, a place where everything feels like it isn’t enough,I often feel that I’m insufficient without more experience, and therefore at risk of lowering my boundaries and putting myself in unsafe situations. Ironically, feeling like I’m “too much,” like my needs are a burden, is also a form of scarcity: it indicates that I don’t think I’m worthy of my needs being met. When I’m approaching sex from a place of abundance, I can value my needs and feel that they’re just right, and I therefore can communicate both pleasure and boundaries with equal confidence and clarity. Coming from a place of abundance means that I can be with another person while also being there for myself. The more I practice identifying how I’m feeling, the more vulnerable I can be and the more pleasure I can bring into my life.

What do we count as experience?

Many people say that they don’t have any sexual experience, but when they say that, what they usually mean is that they don’t have any experience with another person. Your most important sexual relationship is the one with yourself, so you'd be doing yourself a disservice to not think of masturbation⁠ as experience! The ability to bring yourself pleasure is a beautiful and important act; to get to know yourself is to be fully engaged.

Masturbation is a great way to learn about which parts of your body are erogenous zones⁠ and sensitive to touch, as well as what kinds of touch you enjoy (like touch that’s slow or fast, gentle or more intense, has rumbly vibration or high speed vibration, more or less pressure, and so forth).

It can also be useful to journal about your masturbation practice, both before having sex with another person, but also in general. You can think about and write down how and when you get aroused, if you have certain fantasies, if you watch porn. By journaling about masturbation and your feelings of sexual desire, you may start to see some useful patterns over time. You can also make a list of sexual activities and mark if each activity is a yes, no, or maybe, as in, you would definitely try the activity, definitely wouldn’t, or you aren’t sure. If and when you have sex with someone, you don’t ever have to be open to everything. You can go into sexual situations with this list and your own experiences by yourself in mind, and ask partners to tell you about their “yes/no/maybe” lists, or make a list together with a partner. Both of you can also talk about what you know from your own masturbation practices together: even if you’re both new to sex with a partner, masturbation gives you plenty of experience you can bring to the table.

It’s best to be honest with new partners about your sexual history, even if you're self-conscious about not having much or any experience with other people. Pretending you have more experience than you do can feel like an easy fix in the moment, but can actually set you up to feel performance anxiety during sex. If you feel that you have to be dishonest in your sexual responses, it may make you feel like you have to perform “right” during sex, like you need to prevent your partner from thinking that it’s your first time. You might also feel like you have to do anything and everything a partner wants so you don’t have to risk them finding out you’re new to this: being dishonest about your history can put you at risk of feeling like you have to do things you don’t want to do or go without limits and boundaries.

The reality is that every time anyone has sex with a new partner, it’s a “first time.” It takes a lot of communication⁠ and experience with a partner to know what pleases them and for them to learn how to please you, because we don’t all like, need or want the same things or enjoy them the same ways. Even when you have consistent sex with the same partner, each time is unique and requires enthusiastic consent⁠ . Being able to communicate to a partner that you are new to having sex with another person or to a specific sexual act allows you to get the good stuff from beginner’s mind, where you can learn with curiosity, laugh at how sex is often funny, and appreciate the whole experience. Admitting that you are new to something is vulnerable, sure, but it also gives you an opportunity to see if your partner shames you or treats you with care, which is important information. If they are giving you signs that they will only accept the fictional person with a different life experience that you’re projecting, you’re allowed to say no and leave. If they accept you as you are and really want to be with you, you have an opportunity to explore, learn, and have fun. Furthermore, everyone has different preferences, so you should always ask your partner what makes them feel good and what their boundaries are.

Authenticity and identity⁠

I’ve struggled with showing up as my authentic self in romantic and sexual interactions and relationships for years.

When I was 18, I left my homogenous, mostly straight high school and started college on a campus that was nationally known for its queer scene. I’d imagined college as a queer utopia. I wanted to find love and to feel attractive. I imagined being home during a winter break and telling my friends from high school that I finally had a partner, that I had lots of sex, and that I was thriving.

I quickly learned that a large queer scene also meant complicated social dynamics, seemingly exclusive⁠ friend groups, highly developed aesthetics, and the intensification of all my insecurities. I was myself – nothing had changed except for my environment and an opportunity to start again – but I still carried all of my history. For a bit it was refreshing to have lots crushes, but I felt heavy with loneliness when they didn’t reciprocate. If I was living in a queer utopia and I still felt unwanted, what did that say about me?

Even though I wasn’t putting words to what I was doing, I was exploring gender by Halloween of my freshman year. Over the next couple of years I began to wear dresses, skirts, crop tops, and makeup. At the beginning of junior year I started to use they/them pronouns and identified as non- binary⁠ . During this time I didn’t date anyone, but I had some hookups – mostly from dating apps and occasionally from meeting people at parties. Even though I was not a man, I still sought out gay⁠ men, never showing them the authentic femme⁠ side of me. Being femme in a body that was read as a “boy” was constant cognitive dissonance: wearing a dress and makeup made me feel like I was the truest version of myself, but I knew that I never got the type of sexual and romantic attention I wanted when I was femme in public.

By senior year I started to identify more with being a trans girl and realized I wanted to get on feminizing hormones⁠ . I had to wait a year to start hormones, but I while I waited I felt more and more certain of how I wanted to embody my gender. During this time I started hooking up with a trans friend of mine. For the first time, someone was seeing my full self and honoring and cherishing the trans part of my identity.

I got on hormones within a few months of graduating. During the beginning of my hormonal transition⁠ , I was filled with anxiety over not being sure how other people were gendering me and who was attracted to me while my body was changing. I couldn’t seek out gay men anymore -- not only would it pain me to pretend to be someone I wasn’t, but I could no longer hide my budding breasts, which were the biggest sign of my transition at that point. At the same time, I didn’t believe that any straight man would find me attractive during my early transition. I brought these anxieties to my therapist. She helped me realize that seeking out gay men was self-sabotage, knowing that they would soon no longer find me attractive as I got deeper into my transition. I began to realize that my dating pool was bisexual⁠ and pansexual⁠ people, especially other non-binary and trans people – people who would find me attractive no matter how I transitioned, who wouldn’t put pressure on me to pass as cis. Now, two years into my hormonal transition, I’m also somewhat open to straight men, but he would have to be someone who is knowledgeable about gender, doesn’t fetishize my trans-ness, and wholeheartedly supports me being my authentic self.

I bring up my own story not to imply that all of us will have similar experiences, but because I think queer and trans people deep in their self-exploration journeys often self-sabotage when it comes to bridging the gap between our desires and our actions.

I can see now that I was seeking to feel wanted in environments that were just never going to affirm me. I can also hold compassion for my younger self who kept returning to these environments, hoping that each time would be different. Eventually I realized that I was never going to heal this way, and I put myself in new situations where I could trust that if someone wanted me, they were also seeing me clearly. Dating isn’t simple even now, but I am courageous in being myself and fierce in defending my standards. This vulnerability has brought me more pleasure, intimacy, and connection than I have ever had in my life so far.

I can see now that feeling like I was “behind” pushed me to search for desire in places that wouldn’t let me bring my whole self to the table. I can also see that spending time exploring and clarifying my gender identity⁠ eventually led me to seek out partners who could affirm my identity. Of course, people experience desire for only the surface of people all the time, like when you see someone for a moment and find them attractive. Ideally, though, when we become more intimate with someone, we bring our whole selves to the relationship. You may be first finding words for some of your identities, while other parts may be set, and other parts may keep evolving. It’s okay to tell a partner that you are still figuring out parts of your identity. Allowing other people to see you is an act of vulnerability. In the book Daring Greatly: How the Courage to Be Vulnerable Transforms the Way We Live, Love, Parent, and Lead by Dr. Brené Brown, vulnerability is defined as “uncertainty, risk, and emotional exposure." If you are boldly being yourself, there is always the risk that some people will reject you. At the same time, you will know that the people who do desire you, who make an effort to get to know you, who tell you they love you, value and know the real you.

Remember that you're allowed to be discerning when it comes to finding partners. You don't have to accept the first potential partner you encounter because you haven't had experience yet: you get to hold out for the kinds of partner you really want and who feels really right for you. Gauging if you are going to feel safe and affirmed with a new partner takes practice. It’s worth reflecting on your needs on your own or with some trusted people in your life.

Here are some things to consider when getting involved with someone new, especially when you’re new to all of this:

  • You can talk with a potential partner about your level of experience, your boundaries, and what you know you enjoy, before being sexual with them to find out how they respond.
  • You can talk with a potential partner about your identity to see if they treat you with respect.
  • Once you start exploring sex with others, every experience won’t be amazing, but that’s okay, and it doesn’t necessarily mean you made a wrong choice.
  • You can be as selective as you want to be no matter how much or how little experience you have had.
  • Romance and sex tend to open up uncharted feelings in people, and that’s okay! Thinking about something in the abstract often won’t match reality. If you have spent a lot of time imagining these things, stay open to the idea that your experience may end up feeling or looking different than you imagined. Give yourself some space to reflect: it’s useful to journal or talk to a friend. It’s okay to feel somewhat disappointed if the experience is different than you imagined, but ask yourself if you feel safe, if you feel like your partner is listening to you, respecting your boundaries, and actively invested in your pleasure.
  • If you don’t feel safe, if you feel upset, nervous, scared, overwhelmed, or have a gut feeling that something doesn’t feel right, you are always allowed to take a break. You are always allowed to get up and leave. Depending on the situation, you might want to talk it out with your partner, but you don’t ever have to. Some signs of an unhealthy relationship are: your partner makes you feel guilty, their care is conditional, they don’t respect your need for time alone, they put pressure on you to try something that you don’t want to do, and any amount of violence.

You get to decide what it takes for you to feel safe, by the way. You have agency here.

Some final thoughts

People often consider romantic relationships to be in a league of their own, completely separate from platonic friendships. But connection is connection, intimacy is intimacy, and the skills that make for healthy, happy friendships also apply to romantic and sexual relationships. If the idea of beginning a romantic or sexual relationship without romantic or sexual experience is scary, consider the journeys you’ve gone on with friends. Before I ever dated someone, I had already built complex, stable, emotional, life-affirming friendships. I had broken down, emerged through conflict, healed, laughed, broken up with, cuddled with, supported, and loved friends. I had learned to communicate and listen. Consider what your strengths already are and where you can grow.

The gift of being new to things is that you can experience them without pre-existing bad patterns or jadedness. As you start exploring dating and sex, I hope you can approach yourself and your partners with curiosity and gentleness. You’ll probably experience a wide range of emotions, but remember that at the end of the day, dating and sex should primarily be pleasurable and affirming and feel good instead of scary. It’s a good idea to check in with yourself from time to time to make sure you’re having fun and feeling good about yourself in your dating and sex life. You’ll also probably make mistakes and make choices that don’t align with your values, because you’re human.

If you’re reading this, I have a feeling that you’re there for yourself, and you can continue to be there for yourself as you connect with other people. Communicate with yourself and your partners with courage and consistency, have fun, and remember that you are perfectly whole just the way you are right now. You’ve got this.

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  • Lisa Laman

Many social norms, macro or micro, can make it seem like the ideal — or even only! — time to start having dating experiences is in high school. You may get the message that doing it any other time, even just waiting until you’re in college, puts you at  some kind of disadvantage. To go against that grain may inspire some social judgement of you and, at least in my case, leave you wondering if you’re just fulfilling a harmful stereotype about what autistic people are capable and incapable of doing. Even if it’s impossible to remember amidst the din of outside messaging world, there is no one right time for dating. That’s as true for neurodivergent folks, including those of us on the autism spectrum, as it is for neurotypical members of the world.