In Sex, Failure Is Necessary

I’m Alexander Cheves. I am a writer, author, and sex educator. My nickname is Beastly. I give adult advice — no question is off-limits. To ask me something, email AskBeastly@gmail.com or send me a message via the Ask Beastly contact form.

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Hey Beastly, 

I wanted to ask your opinion on my relationship, sex, and how to facilitate healthy conversations.

I am 26, new to NYC and I met a guy who is really amazing. We hit it off and we are on the precipice of becoming boyfriends, which for me is amazing because I have never had one but always wanted one.

He is older than me, with much more experience in terms of life; he’s already been married, lived in NYC for nearly 15 years and its kind of intimidating sometimes to see myself as someone with whom he wants to pursue a relationship because he is hot enough that he could have anyone. But also that makes me nervous because I do not have nearly as much sexual experience as he does.

I have had sex a handful of times with different guys that never seemed to give me the enjoyment that I have been craving from sex. I have bottomed 2 times and both were terrible experiences which have kind of left me scared to try again without someone I trust. I see him as that person.

We have not had sex yet, but we have had some frank conversations about sex, our differing HIV statuses and how to approach it from a physical standpoint. All have been great but I am concerned because right away he gave me some hard and fast “no’s” to things that he is not into sexually or that is averse to. Additionally, I know that he is into several kinks that I do not think I am. 

I am concerned because I am at the start of my sexual awakening and still discovering what I like and don’t like. I find kind of retaining to know that the things he isn’t into are things I wanna explore while other areas that he is interested in are scary and foreign to me so I am not really chomping at the bit to explore those kinks. I wanna know what to do so that way I feel not feel so weird about our differing interests and so I can enjoy this sexual journey we’re about to begin. 

PS I think his bestie subscribes to your blog so I would prefer the post be anonymous, or call me “Kevin” (my alias lol)

Hi Kevin,

Thanks for your message, and welcome to NYC. I moved here just under a year ago and I’m dating someone older and more established here, so I guess you could say we’re in similar places romantically. He has a tighter network of friends and a well-paying job and I have neither. Yes, it’s intimidating.

Adjusting to this city is hard enough without navigating a new relationship. Whenever I feel depressed and overwhelmed, I remember my college poetry professor, Angela. She was more mom-like than my other professors and I really needed that.

One day, a classmate came in with a silly poem about a pumpkin. In the poem, the pumpkin got carved out, cut up, and turned into a garish, grinning jack-o-lantern. The classmate had just broken up with her boyfriend who cheated on her, so we all knew what the poem was really about — her.

As soon as she finished reading it aloud to the class, she started crying: “I…am the pumpkin!”

We felt embarrassed for her. No one said anything. Everyone stared at the floor.

Professor Angela was quiet and let the girl cry for a few minutes. Then she sat on the corner of her desk, crossed her arms, and said this:

“You think you hate him but you don’t. You tell yourself that you will never do something like this, you’ll never hurt anyone this badly, but you will.”

Angela continued: “This may not help right now, but you’re supposed to be doing this. You’re supposed to get your heart broken and get it broken over and over so that you can learn how this feels. Learn it and learn what to do with it.”

Then: “I know you’re all working hard and trying to figure this stuff out, and I just want to remind you that you’re just kids.” Then the professor started crying — the first and only time I have ever seen a teacher cry. “You’re just kids,” she said again. “You don’t have to put yourself under so much pressure all the time.”

And then it was just too much. I felt close to tears because, yes, I was terrified of love and sex and my body and the future, and the relationship I was in at the time was difficult and consuming, and I had so many questions. What did I like? What did I want? Would it work?

I still have questions like this, all these years later. With every new discovery — every area of sex in which I learn to feel confident — new questions arise. And this is how it will be for the rest of my life, I hope. Such is the price of adventure and exploration. You’re supposed to be having these questions and living with this uncertainty. That’s the price you pay by moving to a big city, trying to establish a life here, trying to find love.

I know you have a lot of questions and uncertainties — only some of which are presented in what you sent me. Here you are, enchanted by a man whose sex life seems stranger and more experienced than yours, who is into things that don’t really seem to push your buttons. But you really like him.

You’re supposed to be doing exactly what you’re doing. You’re supposed to try things out and risk failure in order to grow. You’re not supposed to be certain of your sexual interests, what kinks you’re into, or even what kind of relationship you want. We learn these things by trial and error. The relationship might fail. Failure is good.

Try the relationship. Try bottoming. Try out his kinks and interests, even if you don’t think you’ll enjoy them. How else are you supposed to discover new things? (I suggest trying everything twice before deciding it’s not for you.) You’ll never advance sexually unless you learn from people with more — and different — experience. You’ll never learn how to “facilitate healthy conversations” until you have to communicate with someone in order to keep dating them. You won’t have healthy conversations right away. You will fight. You may even get your heart broken. And that’s how you will learn.

Every relationship involves significant differences — differences in sexual appetites, differences in taste, differences in income, differences in experience. The only way to manage these differences is to talk about them and keep an open mind.

So, you both have different interests. The best option is for you to both be equally willing to try out what the other person is into. If he isn’t as willing to try out your sexual interests or if you are absolutely unwilling to try his, you’ll have to either a) decide to live without indulging your kinks or b) indulge them with other people in a non-monogamous relationship. Those are your only options.

Bottom — unsuccessfully, then try again, and again, and again, ad infinitum— until it starts to feel good (I can help with that a little bit). This relationship probably won’t last forever, but you’ll have loved someone in New York. Welcome to the city, baby.

Love, Beastly

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