Let’s talk about sex

About that time my partner’s orgasms shook the internet

It’s been a long time since I’ve talked about sex or relationships on the internet. And the last time, I really didn’t even touch on sex — I wasn’t confident enough in myself or how to speak to my sexuality to wade into that topic. Instead, I shared what I’d been learning about non-monogamous relationships (i.e. how to ethically have more than one intimate relationship at a time). Many responses were harsh and assumed negative intent, which is another way to say: just another typical day on the internet.

If it’s not completely obvious, because it takes so much less effort to criticize than to meet someone in good faith with comparable vulnerability and curiosity, it turns out many people don’t. And so I decided that opening up about opening up was best reserved for private communications (probably in person) rather than the public internet. And so that’s how I had conversations about these topics for the next four years.

During that time, I voraciously learned about relationships and sex and had all manner of conversations (in person) and it’s been great. I’ve discovered much, and share when I can and when it’s appropriate and when I think it’ll be helpful. I don’t have anything “figured out”, but I have a bunch of useful experiences to reflect on and questions to ask in the moment. As I’ve integrated these things into my life, my thoughts and the way I understand myself have changed. And my behavior has too.

For example, I’ve started sharing more sex-positive content in my Instagram Stories. But since that content goes away after 24 hours, no one’s really had much of a reaction. I also post and collect sexual wellness products on Product Hunt, seemingly without raising any eyebrows (at least as far as I know!).

So as I’ve become more curious and open-minded about sex and my sexuality (a topic I know realize I need to expand upon in another post), I’ve gained comfort and confidence with both. And now, it feels disingenuous to not express those things, somehow, in my digital or public personae.

With the explosive rise of social media, authenticity has become the coin of the social realm. But identity and authenticity are not realized through the same machinery, a fact previously lost on me given the automatic privilege conferred upon me by happening to be born white and male. One benefit is that I’ve gotten away with treating my internet identity as fungible and malleable for so long, which inured me to the headwinds facing marginalized groups in their baseline ability to express who they are without fear of reprisals or abuse. And while what I’m about to describe to you might seem superficial or self-aggrandizing, this recent experience may be one of the first times in my life when I’ve had to reckon with an emergent conflict between revealing more of my secret self with the apparent need by a public (or at least a public on Twitter) for me to maintain their stable perception of me. But without desiring to rub my secret self in anyone’s face, I no longer feel compelled to tuck this part of me away, especially as I’ve released the shame and discomfort I once had towards it.

Who’d you write your Twitter bio for?

So let’s talk about the thing.

Recently, I edited both my Twitter and Instagram bios.

I’ve always been coquettish with my internet identity, but overall mine has been shelf-stable since I started identifying as the “inventor of the hashtag” when Twitter attempted to seize it as its own a few years back (they reversed themselves). Since then I’ve included that distinction (plus past employers and professional roles I’ve had) in my bio. There was this one time when I became Chris Messina The Actor (aka #OtherChrisMessina) for a couple days and confused a bunch of people who got very excited when I sent them kissy-face emojis (😘), but otherwise, while I try not to take myself too seriously on the internet, I’ve never been quite so… * ahem *… risque in my digital plumage until this latest change.

And to be fair, I’ve kept it pretty conservative for good reason (see my aforementioned attempt to talk publicly about relationships). Kara Swisher has long pointed out Silicon Valley’s Peter Pan syndrome and it’s true: it’s a place where men haven’t been asked to grow up. They are infantilized and their behavior excused as long as their tech companies are moving fast and breaking things and/or racing towards an IPO. Talking about sex publicly hasn’t offered much reward relative to the risk.

I left Uber right before Susan Fowler published her internet-breaking piece, and so I don’t enter the fray casually. I mean, who am I — as a white cis male — to talk about sex in any way that isn’t reverent or detached — or perhaps even apologetically? (We white cis men truly have much to atone for, but might there also be space for lightness and a healthier, more integrative approach?)

So anyway, what happened was that my romantic partner messaged me about a new connected sexual wellness device (read: vibrator) that she’d discovered and we were going back and forth about it when she proposed that I alter my recent oh-so-earnest bio (i.e. “On a mission to make myself more useful.”) to read, “On a mission to give my beautiful partner the most orgasms she’s experienced in one day.”

And so I did — on both Instagram and Twitter.

I thought it was funny and crass and like “no one” would even notice!

It’s subtle, right?

But one friend did notice, and when she asked about it, I shared the story and she nodded with an impish and approving smirk and declared it “super ballsy”.

When my partner finally saw it, she texted, “OMG! How long do you plan on keeping that up there?!?!”

And I responded, “I’m curious who will notice and if anyone will say anything… Maybe I’ll change it before my next talk…? 😜

“You’re crazy. Let’s see who does notice it.”

And then, sure enough, within 24 hours some people did — sharing screenshots to their active Twitter followings… including Ed Zitron (43K followers), Prof. Brian Krassenstein (23K followers, a parody account), Kate Sloan (10K followers), Zach Kahn (5K followers), Jenn Schiffer (32K followers), Jason Calacanis (300K followers), and others. (I mention their follower counts only to indicate how this amusing little nothingburger inside-joke suddenly had the potential to be seen by… a lot more people.)

Reactions varied from concerned (“thought to message him to see if he was hacked”) to comical (“The guy who invented the hashtag has one of the weirdest and horniest bios in town”) to sarcastic (“This bio is a masterpiece.”) to… derivative (“On a mission to give my wife the most number of unicorn investments.”).

Seeing as it was just another typical day on the internet, the replies were unsurprisingly less good-natured and aren’t worth digging in to… but there were… many.

Expecting to expect the expected

In some abstract way, I feel like this is my personal headphone jack moment.

That is, by declaring myself to be someone or something other than what people were expecting — I caused such severe cognitive dissonance in people that the most viable responses included ridicule, rejection, repression, skepticism, shame, or a demanded reversion back to my previous and thus more familiar state.

To make the analogy: previously people defined an iPhone as having a headphone jack, but then “courageously” Apple decided that an iPhone need not be defined by a headphone jack after all! And everyone lost their shit.

So at least in some cases, it seemed like my bio freaked people out because they needed me to be the “inventor of the hashtag guy or whatever” but with my new bio referencing sex, I had fucked with the microscopic mental space they reserved for me (or for “people like me”, i.e. “techies”) and had broken their brains at least a little, which was just too goddamn much.

That, or… sharing one’s intimate sexual exploits in a Twitter bio is just weird.

Or both.

Okay, so I can understand that some people might be offended by imagining other people having or engaging in sex — especially if you normally don’t associate them with sex… but really though? Don’t most people (though certainly not all, and that’s ok too), at some point in their lives, have or engage in some form of sexual intimacy? If so, and in the post-internet, post-porn world, are we still so squeamish about the topic when it’s discussed in public? Is it really kinky to do so? If the president can carelessly talk about nonconsensually grabbing a woman by her genitals, must we also ban talk about consensual intimacy?

Moreover, isn’t this taboo and our inability to speak openly and intelligently about sex and sexuality a key element of Silicon Valley’s juvenile toxicity towards women and non-cisgendered individuals? Isn’t it the general ignorance and lack of awareness preventing us from having plain and matter of fact conversations about consent, desire, curiosity, and healthy sexual wellness? Hasn’t the lack of diversity and a healthy, respectful dialog about sexual identity contributed to the unaddressed corrosive abuse that’s haunted social media from the outset? Isn’t this aversion one explanation for the pleasure gap, and what is also motivating companies like Andrea Barrica’s O.school and OMGYes?

Where does healthy sexuality fit on the social web?

Look, I’m far from being an expert and I am deeply aware of that — but at the same time, should stating an interest in offering my partner orgasms be controversial?

Ok, if you don’t like the context of expression, let’s separate that out: if not on one’s Twitter bio (which is about that person, mind you), where should one reflect the sundry parts of her or hisself, including their sexuality? Why is healthy sexuality or sexual desire inappropriate in one’s Twitter bio while struggle porn and “crushing it” at your startup is celebrated?

Why is stating an interest in offering my partner orgasms controversial?

To be clear, my sexuality is not going to be what I solely define myself by going forward. But my sexuality and sexual identity is absolutely part of who I am — and always has been. I just wasn’t able to share this part of myself without fear and shame years ago. But I am now at a place where I can do that. And given that Twitter and Instagram are my two primary platforms to share my life and my thoughts, why should I leave out parts that are just as vital and necessary as my interests in product, technology, design, culture and startups?

But — I get it. If you don’t want to hear about these things, that’s totally cool. I invite you to unfollow or block me — no hard feelings. There was a time when I might have done the same thing to myself if I were in your shoes. But, if you’re a curious person and perchance open to learning more about these topics — occasionally (and not necessarily explicitly) — then stick around. And if you’re interested in sharing your own lessons and journey into developing and deshaming your own sexuality, drop me a note. I find connecting to people and learning new things very satisfying.

Written by

Inventor of the hashtag. Ever-curious product designer and technologist. Previously: Google, Uber, Molly (YC W18).

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