How do I share my more selfish or sexual intentions with someone?
...especially if I fear the other person wouldn’t share them
A friend asked me this question in late 2023, and it’s been living rent-free in my mind for months. Here’s my first pass at an answer, based on my last 300+ dates and conversations with over 1,000 friends and colleagues. Please reach out with feedback and insights based on your personal experiences!
As deeply social creatures, we crave connection and belonging.
As deeply sexual creatures, we crave exploration, novelty, and pleasure.
As internet-connected creatures who invariably accumulate both first and secondhand trauma with each passing year, we may find it ever more challenging to put ourselves out there and share our actual intentions and desires with the people around us. Rejection is scary. Jeopardizing friendships we already have is also scary.
However, as dynamic, generative creatures living at the social and technological cutting edge of human history, we are far more empowered now than ever before to rapidly learn best practices from one another and apply them day over day in order to overcome just about any obstacle. Let’s dig deeper…
Step 1: Assess your context
Each unique context may require a differently tailored approach. Is this someone you’re hoping to message on a dating app? Are they already flirting with you on the app? Is it a long-term friend? A coworker? Someone you’ve gone on a first date with? Do you already see them with any regularity? Would your ask of them also implicitly entail a request for more time spent together? Do you know if they have that time available in their lives? Have you ever talked about dating/sex/intimacy with them before at all?
Remember, humans exist across complex patriarchal and interconnected societies full of gender imbalances and wildly differing experiential realities. A woman signing up for a dating app can receive over a hundred messages the very first day. A straight 40-year-old man on Tinder may need to swipe on over 1,000 people to receive a single match. Women walking down the street can receive multiple unwanted catcalls per day, while men can walk tens of thousands of miles throughout life without receiving a single compliment or romantic overture in their direction.
Step 2: Inquire about their context
Cultivate spaces where you can speak candidly about things you’re thinking about in life. Do so in groups if you don’t yet feel comfortable asking the person to join you one-on-one. Strive to better understand their priorities, preferences, and the general cadence of their life, including whether or not they’re even open to new romances/dalliances. Consider hosting / inviting them to:
hikes / park walks / food truck tours
picnics / volunteering / concerts
movie nights, dinner gatherings, slumber parties
coworking / passion project / crafting days
When together, practice deep listening. Give them your loving, inquisitive attention. Show curiosity about the spheres of their life that they’re investing time and attention in. Ask them about experiences they’ve had that felt particularly salient, satisfying, indulgent, or frustrating. Be willing to share your own stories, so it doesn’t feel like they’re being interviewed. Depending on context and vibe, conversation can venture into more romantic or sexual directions, but if you pursue those avenues exclusively it could feel like you’re not holding space for what they actually feel is most alive for them. Always respect where they are more than where you want them to be.
Questions to solicit more of someone’s life / dating / romantic context might include:
How do you distribute your time and attention across a given week? Any big priorities that persist week over week?
Did you have any really good dates this year?
If you actually find someone really attractive, what do you do from there? Do you flirt with them? Do you wait for them to come on to you? What do you wish they would actually do?
What’s something someone’s done before with you that felt really attractive/magnetic?
Are there any romantic or erotic movies/scenes you’ve seen that captured something you thought would be really fun to try [
with me]?*
*Note: if your tone/inflection implies the “with me”, you’re at risk of setting this person up for failure and disappointment. Their answer must not be tainted by your projections of what you want them to be doing with you. They’ll learn to mistrust your questions, because you’ve got a hidden agenda. You must be prepared for them to not be interested in you, sexually or romantically, at all times, and have that not be an instant dealbreaker. Remember, this person is a valid and worthwhile human being regardless of whether they desire any degree of romantic or physical involvement with you. Perhaps this is also a relevant time to brush up on your skills in detecting flirtation.
As conversations progress, strive to embody equanimity. Do not knee-jerk judge people if and when they share their preferences, kinks, or traumas. No sulking if they reveal they’re not even interested in people of your gender identity. No closing yourself off and becoming sullen if they tell you candidly that they don’t want to have sex [with you] [tonight]. Thank them for their vulnerable honesty and straightforwardness. They shared their truth with you. Remind them why you appreciate them. You may not be compatible on the romantic/sexual frontier at this moment, so consider what can be learned and discovered on the friendship frontier.
Step 3: Show introspection, vulnerably, and a spirit of co-creation
Be transparent and candid in sharing what sorts of friendly, flirtatious, sexual, romantic vibes you’ve resonated with in the past, and which ones you’re trying to call into your life now. No one can read your mind and understand what you want, but once you’ve verbalized it, they can begin the process of thinking and feeling through what that might look like one day, perhaps with them directly, or with someone they know.
For instance, if you tell someone about three different dates you’ve gone on and what sorts of intimacies you encountered and built on those dates, this gives them three new possible frameworks for understanding you, and consequently, what they could potentially do with you, if your compatibilities align. They may have never even conceived of these possibilities until you shared them. By introducing these lived experiences (or even simply theoretical/nascent desires) of yours, you’ve opened the doors to a multitude of new possibilities that they can now feel empowered to acknowledge and validate, or potentially pursue.
Be prepared to read the room and generate flirtatious energy. Are they making a lot of eye contact with you? Are they squaring themselves to you, touching you, smiling, deepening the conversation as you go, sharing more vulnerably? Reciprocate when desired. Are they asking you more nuanced questions about your relationship backdrop/availability, and/or practical questions about when you might see each other again? Great! You’re on your way toward a deeper connection with someone who you’ve taken the time to thoughtfully get to know.
Step 4: Champion your own boundaries and show gratitude in the face of rejection
Voicing your own needs, desires, and boundaries gives others the frameworks and effective modeling to do the same. Committing to your stated boundaries and following through on your stated desires sets a precedent for your own integrity, confidence, and self-respect, which is universally attractive.
The more difficult part can be validating and honoring the boundaries and even overt rejections from others. It can feel jarring, alienating, and even re-traumatizing to be rejected, which is why it’s particularly important to reflect on why and how people voice their rejections, to better acquaint yourself with the endless contexts and priors that people bring to the table in every interaction.
On the topic of sexual rejections, alone, there can be countless reasons for someone pumping the breaks or tabling sexual activity altogether. Below are just a few examples of sexual rejections I’ve witnessed over my years as a dating coach:
I don’t want to have sex with you.
...because I know from my history I’ll feel very attached, and I know you and I want different things, so I want to spare myself that pain.
I don’t want to have sex with you tonight.
...because I’m too tired / on my period / feeling bloated / too sore from that threesome I had last night.
I don’t want to have sex with you right now.
...because your energy is all over the place and I don’t feel grounded. I don’t feel aroused or erotic. I don’t feel like you’re really listening to me, seeing me, understanding where I’m at.
I don’t want to have sex with you right here.
...because we’re in the woods and it’s really cold / because I don’t want my roommate to overhear.
I don’t want to have sex with you.
...but I would love to go down on you. And if I get super horny from it, I reserve the right to ask for sex then.
I don’t want to have sex with you.
...but I would love to go down on you, and then cuddle and watch a romcom.
I don’t want to have sex with you.
…because I’m feeling paranoid about pregnancy risk right now after my recent scare. But can we can cuddle and talk about it and then make dinner together?
When people share their boundaries and even rejections with us, they’re inviting us to respect their truth as they know it in that moment. In respecting their truth, we build respect and rapport. If we fail to respect their truth, we trigger alienation, fear, and frustration.
Step 5: Don’t fixate; Continue building out your own life path
Not all paths in life lead to you and any specific person doing any specific thing. Don’t get hung up about it. Accept this in stride. There are few things less attractive than someone pinning the whole of their self-worth upon any given subset of your reactions/interactions. It’s critical when building rapport with someone that you don’t get swept away in your own mental models about them, or worse, contorting your own life priorities to conform to theirs. You absolutely need to continue living your own independent and fulfilling life.
If we truly wish to dissolve the harrowing feeling of existential anxiety through love, it must be by the relentless cultivation of our sense of self and the ability to love. We must maintain tremendous respect for our partner’s individuality and uniqueness. We must declare to “want the loved person to grow and unfold for his own sake, and in his own ways, and not for the purpose of serving me.” In this way, love is not an emotion but rather, an attitude, “an ordination of character”; not something we “fall into” but rather, “stand in” and the learning and practicing of how to love becomes not an emotion but a skill: an enterprise that demands our full attention on a daily basis.
~ Erich Seligmann Fromm, in The Art of Loving, via http://m.huffpost.com/us/entry/us_575fb5c0e4b072d1185b1434
Encourage those around you to live their best lives, and do what you can to help them in that process. Ask others for help and insight when you need it. Every now and then, people might see that project you’re working on, that event series you just kicked off, or that casual fantasy you verbalized the other week, and one day feel inspired to join you. 💖
"There is a vitality, a life force, a quickening that is translated through you into action, and because there is only one of you in all time, this expression is unique. And if you block it, it will never exist through any other medium and be lost. The world will not have it. It is not your business to determine how good it is, nor how valuable it is, nor how it compares with other expressions. It is your business to keep it yours clearly and directly, to keep the channel open. You do not even have to believe in yourself or your work. You have to keep open and aware directly to the urges that motivate YOU. Keep the channel open.”
~ Agnes de Mille, “Dance to the Piper and Promenade Home” (1982)
Want to explore these topics further? Schedule a call with me anytime to chat about dating, friendships, relationships, and more. I’ve been coaching on these topics for nearly 15 years. My first call is always free. I want to get to know your life a little better to see whether I can even realistically help. Sometimes I can help enough on our first call that you can set yourself on a solid course for a several weeks or months. I like to cultivate habits of never pressuring people toward specific outcomes. That matters as much when coaching as when simply talking to people who reach out on the internet.
I also hate paywalls so I made this article free. I felt a little iffy about paywalling commenting, but the main reason I began publishing here instead of on Medium was how many comments came from bots. If you want to go down a rabbit hole about the bots and scammers throughout the online dating ecosystem, you’re in luck. I wrote about it a few months ago:
Inside the harrowing ecosystem of bots, scammers, catfish, self-promoters, and rogue AI on modern dating apps
"What's something that feels like it should be illegal to know?"
Oh, you’re still reading? Here are some (hopefully) fun and useful links: