20 Lessons I Wish I Knew When I First Started Dating: An Open Letter to My 13-Year-Old Self

Hey there, little one,

It’s nearing the end of eighth grade, and a nice boy in metal shop class just asked you to be his girlfriend. You’re excited, terrified, and have no idea what to expect out of this relationship, but it will be the first of many to come.

It’s been nearly twelve years since I was in your shoes, and I promise that you’re in for an exciting journey.

You will gradually learn from these relationships what you like, what you don’t like, what you need, and how to communicate all of that with your partners. You won’t experience the kind of mind-blowing, gut-wrenching, head-over-heels love that other people talk about, but you’ll grow comfortably attached to some wonderful guys, and you’ll have a lot of fun with them. Your dating mindset will improve, evolve, and become more fulfilling than you ever thought possible with each new relationship.

You don’t know it now, but you have a lot more in common with the kids in your grade than you think. Adolescence is a trying stage of life for all of us, but you’ll like the increased freedom that accompanies adulthood (…minus the unfortunate increased necessity of wearing pants that also accompanies adulthood.)

1. No one has their shit together. Ever.

We fake it, even as adults, both in-person and via social media, by trying to make our imperfect lives look spectacularly successful and happy to other people. We also try to look like we know what we’re doing in bed, but a lot of us don’t, and that’s okay. Your partners are just as scared and clueless as you. Talk to them. Authenticity fosters trust. The more thoroughly you can both get on the same page, the better.

2. None of your partners will ever care about how your body looks as much as you do.

Despite the pervasive hypersexualization of women’s bodies (especially breasts) and the constant cultural influence attempting every day to shame you for the ways in which you do not live up to these unreal, unachievable ideals, most guys won’t care. Really.

They don’t care that your breasts are small, how your public hair (or stubble) is shaped, or that your reptilian skin sheds constantly. Rather, they are surprised and thrilled that you want to take off your clothes, touch them, and be touched by them. They’re also terrified of disappointing you once their clothes come off, too.

The more time you spend lounging naked by yourself, the more you’ll come to accept, embrace, and stop dwelling on anything you once disliked about your body. Learning to sleep naked toward the end of college will also help tremendously. (Long live Naked Fridays!)

3. Most of your partners won’t kiss and tell.

You’re terrified that they will tell their friends everything you each shared, and that your peers will think you’re promiscuous. Luckily, the guys you select won’t tell anyone publicly — except for one who does, and lies to his entire first period class that you had vaginal intercourse together in a hot tub. (Fortunately, your source for this disclosure reassures you that no one believed him, and it’s never brought up to you again.)

Flash forward a handful of years, and your outlook will completely change. You will actually encourage your partners to tell whoever they wish anything about your romps together. Why? …because you will want their loved ones to learn from your experiences. It’s incredibly freeing to feel like you have nothing to hide, and it’s fulfilling to feel like a role model for your younger friends who are learning these lessons for the first time.

4. Orgasming in a partner’s company is a lot more difficult than orgasming alone.

There are more physical, auditory, olfactory, and emotional distractions during partner play, so it’s harder to focus on the sensations you experience in-the-moment. The more you master relaxing in sexual settings, the easier this will be. Fabulous toys will make a world of difference, too. (Long live vibrators!)

5. Not everyone will orgasm during every sexual experience, and that’s just fine.

You and your partners will still have a great time, regardless of the end result. The problem is that your post-adolescent partners will always be more bothered than you will when either of you doesn’t climax because they’ve been socialized (via porn, their friends, the media, etc.) to view orgasm as the ultimate sign of successful sexual satisfaction. I’m still not sure how to relieve their frustration, but snuggling, caressing, and discussion are my favorite go-tos.

Sidenote: In high school, you’ll be unaware that orgasming is even a possibility for you, and you’ll assume it’s something that only your male partners experience. Because you won’t discuss it with them at the time, you’ll later wonder what their expectations were, overall. (To any of my ex-partners from adolescence reading this, I’d love to hear your feedback.)

6. Every single orgasm will feel somewhat different.

Yours will vary widely in length and magnitude, depending on which parts are stimulated, and how, and for how long. Even now, I’m still figuring out what causes those differences within our body, but it’s a fun journey.

For you, orgasming feels best when you’re in an environment where you can allow yourself to “go with the flow”. You’ll enjoy learning to stop withholding your reactions — to moan and wriggle and gasp, to arch your back and extend and contract your limbs, to twist your neck and your head, to savor the alternations of muscle contraction and openness. When your body is able to freely respond to marvelous sensations as it experiences them, the sky is the limit for the pleasure you (and your partners) can create.

7. Every single crotch will look somewhat different, too.

When you take the time to look closely, genitals are all marvelously unique… skin folds and flaps, colors, and textures; hair length, color, and growth patterns; which flesh mounds do what, and which are more sensitive to what kinds of touch; etc.

Of particular note, your partners won’t care that your inner labia are longer than your outer ones — or if they do, they’ve never called attention to their thoughts. You’ll be horrified when you learn that many women choose to have their genitals surgically altered to make them look more generic and uniform. (Ladies, this type of internalized body hatred needs to end.)

8. Not everyone will achieve orgasms the same ways.

Yes, high school handjobs were pretty easy because all of your partners climaxed the same way, but that was likely more from hormones and inexperience than skill.

Don’t approach any sexual settings assuming that you already know how to tease and please your partner’s body. Ask questions and (consensually) experiment often, not just when you embark together on a sexual relationship. It’s an ongoing learning experience, and that’s part of the fun.

9. Speak up; your partners aren’t mind-readers. Only you know what feels good to your body.

Tell them when whatever they are doing stops feeling good. They can’t read your mind, nor should they have to try. After all, they don’t know how your body works any better than you do, and why would they? It’s yours, not theirs. You’re the one getting instant feedback throughout the encounter, and it’s your responsibility to express your needs to them.

Luckily, you’ll grow very comfortable directing partners, both verbally and by guiding their palms, fingertips, mouths, and penises. You will also teach your partners to regularly request guidance and offer their own to you. Your relationships will benefit immensely from the mutual openness.

10. Just because you don’t enjoy one act with one partner doesn’t mean it can’t be great with a different partner.

You’ll learn to like making out after the first couple of boyfriends in high school. You’ll learn to love fingering in college. And you’ll learn to crave cuddling-to-sleep after college.

The beauty of physical expressions of sexual intimacy is that each of these expressions will look and feel different than they have in the past because you and your partners will be exploring how each others’ bodies uniquely respond. You’ll learn to appreciate which partners do which acts well, and they will do the same for you. Nurture those creative sparks early on, and prioritize their evolution.

11. Don’t assume your partners want to hook up every time you do.

You’ve long been trained that male people are always accepting of any sexual advances from female people, at any time and in any circumstance, but let me nip that falsehood in the bud right now. Not only is that wrong, but it shames men when they decline sexual advances — or worse, guilts them into coercively accepting advances that they do not want to receive.

Your partners have every right to say no, same as you. They will exercise that right, and it is your responsibility to ensure that they feel comfortable freely doing so. It’s not your fault or a reflection on your attractiveness; they just didn’t feel like fooling around right then and there, and that’s perfectly alright.

12. There’s a world of taboo sex out there you haven’t found yet.

Some day, men will be jumping over themselves to ask you for the opportunity to control them sexually. They’ll be hanging on your every word, eager to please you however you see fit. You will learn to become the hunter, rather than the hunted, and you will appreciate the desirability of this niche role. You’ll relish the freedom and autonomy it brings, as well as the opportunity for heightened sexual responsibility and deeper emotional intimacy.

13. Get to know your body and start learning your preferences early.

This will make your sexual health and expression infinitely easier and less scary. It is a lifelong learning process, but it can be fun, too. Read everything you can find about vulvas, then actually take the time to look at and explore the intricacies of yours. Vulvas are not gross, despite what you’ll hear, nor are they scary, once you take the time to get to know them. Start now by taking time to squat over a hand mirror and gaze between those fleshy lips you mercilessly shave. Speaking of shaving…

14. Body hair isn’t a bad thing.

You’ll learn to stop caring about your crotch fur pretty quickly after high school, your armpit fur during college, and your leg fur post-college.

Trimmers are nifty, and people don’t tend to notice subtle body hair. Overall, Mom will be the only one to vocalize her disapproval. None of your sexual partners will care much, particularly because they’re more concerned with your opinion of their body hair (or lack thereof).

You’ll be thrilled to have more free time and less anxiety over something so petty, especially after the hella strong social shame you will feel over anything less than hairless skin throughout high school and half of college.

Stop slaving over your razor. Take a deep breath, hold your shoulders high, and find better things to do with your time.

15. Prioritize a mutual attraction over opportunistic dating.

There will be lots of people attracted to you, same as anyone else, and it’s okay to turn down men whose faces don’t make your heart flutter, men who aren’t good conversation partners, men who aren’t smart enough to maintain your attention, or men for whom you feel any type of hesitation to the thought of possibly dating. That’s fine; there will be plenty of others.

Jumping into a romantic relationship just because someone offers themself to you isn’t a strong strategy. Yes, you will get faster dating experience that way, which has been a marvelous ego boost and fantastic for getting to know more of the ins and outs of both male bodies and of male expressions of sexuality (though far more “outs” at first; the “ins” came later, in college). You will also feel much more emotionally secure exploring your own sexuality within the context of committed relationships, as opposed to casual flings. That was definitely a perk.

However, these impulsive relationships may be why we haven’t fallen in love yet. Although they were committed, they each lacked a deeper platonic appreciation at conception and felt somewhat unnatural, sort of like we enlisted in blind, arranged relationships, then actually got to know each others’ personalities after we were already a couple.

16. Your own looks don’t define your worth or ability as a sexual partner, or in life.

Society has taught you — and will continue to reinforce — the idea that you, as a female person, are to be valued first and foremost by your ability to attract men. Not only that, but you will be taught that the way to attract men is physically, by how you groom and present yourself to the world.

Although this socialization is pervasive and widely embodied by a large number of people, and although you will master the art of visual appeal, you will also evolve past only viewing your ability to express your sexuality visually. You will deviate from that model and learn how to express your sexual influence in speech, in writing, and through behavior. You will be able to excite your sexual partners without lifting so much as a finger, instead utilizing your attitude, your tone of voice, your posture, carefully crafted facial expressions, and strategic speech.

Once you free yourself from the confines of viewing your sexual prowess purely in terms of a conventionally attractive visual presentation, your self-esteem will flourish like never before.

17. You will also learn about terrible, sadder things.

You will grow furious that rape is never called rape on television, that media reports inaccurately brand the crime as “an alleged assault”. You will feel nauseous each time you hear someone publicly question the integrity of a survivor. You will wish that you had spoken up over the years to every single male person who had ever made you feel sexually threatened, though his behavior, his words, or his imposition into your personal space. You will feel relieved that nothing bad happened by not speaking up all those times, guilty for your repeated inactivity in-the-moment, and devastated for all the victims and survivors whose circumstances were far more tragic. Sexual abuse will become one of your greatest fears, and you will wish that there was more you could do to both bolster survivors and re-educate the abusers and enablers around you. It’s never too early — or too late — to start speaking up.

18. Gender roles needn’t be rigid.

Despite our general (rape) culture enforcing strict heteronormativity, incorporating some genderbending into your relationships can add new depth for both you and your partners. Pegging is a great example.

For an easier, non-invasive exercise, I also recommend switching spooning positions with your partner(s) — if you don’t already — so that each of you gets to feel like “big” and “small” spoons sometimes. It may feel a bit physically awkward for smaller partners to be the “big” spoon (think koala bear latching onto a tree), but that’s okay. The point is for partners to experience a broader range of sensations with each others’ bodies and minds. This is especially important if one partner is used to always being the holder, rather than being held.

19. Communication is key.

I strongly believe that positive communication and trust are the glues that keep relationships strong and secure. However, communication styles and frequency can vary widely among relationships, and especially within sexually intimate ones because of the increased vulnerability between partners. It’s up to you and your partners to experiment and agree to what works well for each of you within the context of the relationship so that you each feel safe, respected, appreciated, and heard.

For example, I like to exchange “good morning” and “good night” text messages with anyone I’m monogamously dating if we’re apart at those times, with a minimum of at least one of these messages on especially active days when we might not otherwise have time to talk to each other. I like for this gesture to serve as a reminder that we are both still committed to the relationship and to each other, despite our busy lives.

I recognize that this may be too much or too little daily communication for you and your partners, and that’s fine. The goal is to recognize and respond to the unique needs of each relationship. It’s up to you to establish and implement what works for yours.

20. Express gratitude to your partners.

One of the best ways to strengthen your relationships with your partners — and this applies to most relationships in your life, in general — is to express gratitude for the role these people play in your life.

On a daily basis at work, I see divorcing couples whose conflicts stem from resentment, alienation, and non-beneficial communication styles between partners. Although I acknowledge that there are plenty of couples who simply don’t mesh well together in a marital relationship and really are better off separated or divorced, I often wonder how many of these relationships could have been (or still could be) salvaged if they were taught how to more effectively recognize and share their feelings with one another, including feelings of gratitude.

People tend to like hearing why they matter, and more specifically, what about them you continually appreciate. Be specific! A blanket “I appreciate you” could feel cheap and insincere to the recipient, but a detailed reminder every now and again (or however often works best for you and your partners — again, relativity is key) with examples of the ‘why’s and ‘how’s of your appreciation can be a powerful bonding exercise.

So, there you have it. Savor the many learning experiences ahead, and always trust your instincts.

Keep your chin up; your peers have just as much to learn as you do. You’re in for a fun ride, and I promise that you will always land on your feet.



P.S. – Connor needs help, but no one knows it yet. You have until September 23rd of your senior year of high school to figure out how to get him that help, or he will die by his own hand. Stop taking your time with him for granted. It’s more limited than you could ever have imagined.


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