Chris Messina has over a hundred thousand followers on Twitter, but he wasn’t thinking about that when he accepted a challenge from his partner to be more vocal about his sexual desires, and updated his profile to include a personal goal of giving her more orgasms. Cut to the following day when people were shocked to see that this tech leader credited with inventing the hashtag had posted something so personal in such a public way. But for Chris, this event was a turning point for him in speaking more freely about sex without fear or shame. In this Taboo Tuesday, Chris talks to Dr. Emily about his journey to accepting himself as a sexual being and navigating a world where many people are not comfortable talking about sex openly. 

Staying emotionally fit takes work and repetition. That's why the Emotionally Fit podcast with psychologist Dr. Emily Anhalt delivers short, actionable Emotional Push-Ups every Monday and Thursday to help you build a better practice of mental health, and surprising, funny, and shocking conversations on Taboo Tuesdays - because the things we’re most hesitant to talk about are also the most normal. Join us to kickstart your emotional fitness. Let's flex those feels and do some reps together!

EPISODE RESOURCES:

Follow Chris Messina on Twitter

Listen to Chris’s podcast, Techmeme Ride Home

Learn more about Chris’s work at chrismessina.me 

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The Emotionally Fit podcast is produced by Coa, your gym for mental health. Katie Sunku Wood is the show’s producer from StudioPod Media with additional editing and sound design by nodalab, and featuring music by Milano. Special thanks to the entire Coa crew!

JUMP STRAIGHT INTO:

(03:01) - Chris's journey to accepting himself as a sexual being - “My process has been one of maybe denying a lot of like my own sexuality and repressing my own sexual desire because I grew up without the ability to trust my sexuality as a man.” 

(05:49) - Going public about his sex life - “For so much of my life, I thought sex was dangerous. Something I shouldn't want. Something that I should repress. Something that my gender tends to use as a blunt instrument or as a type of force against other people to get power from other people. That's not what I wanted to be.” 

(11:40) -  A new age in sex - “The fact that sex is not simply done anymore just for procreation allows us to actually get into the body and to experience things that are actually biologically driven motivators to get us to reproduce.”

(14:42) - Opening up about sex as a society - “I hope in the next 10 to 15 years, these kinds of conversations will lead the next generation to be able to check in with themselves, to be able to say, ‘Is this the right thing for me right now?’”

(17:17) - How more men can open up about sex - “The other thing that's really important is checking your own desire for a certain set of outcomes. If you can separate yourself from having any certain thing happen, I think that also is a really good way of cultivating safety.” 

(22:39) - Chris’s taboo question answered - “I would probably spend a lot of time masturbating because I don't have a clitoris or a vagina, and I'm very curious how they work and what it feels like to have one. To have a part of your body that has 8,000 nerve endings just sounds really intense, but also really interesting.”

All these people were flabbergasted because the version that they knew of me suddenly broke. People thought I'd been hacked. They thought that someone else had taken over my account. Some people were like, "Oh, another fucking guy who wants to have sex. Look at that. That's so unusual." And so part of it was like, "No, you don't understand." For so much of my life, I thought sex was dangerous, something I shouldn't want, something that I should repress, something that my gender tends to use as a blunt instrument or as a type of force against other people to get power from other people. That's not what I wanted to be.

Welcome to Taboo Tuesday on the Emotionally Fit podcast! I'm Dr. Emily Anhalt and I've always loved talking about taboo subjects, sex, money, drugs, death, because being a therapist has taught me that the feelings we're most hesitant to talk about are also the most normal. Join me as we flex our feels by diving into things you might not say out loud, but you're definitely not the only one thinking. Quick disclaimer that nothing in this podcast should be taken as professional advice, diagnosis, or treatment because while I am a therapist, I'm not your therapist and I'm not my guest's therapist. This is intended only to spark interesting conversation. Thanks for tuning in!

Hi, everyone! I'm here with Chris Messina today. Chris is widely known for being the inventor of the hashtag, which is a pretty damn cool mark to make on our modern world I'd say, but if any of you out there have ever done something really notable, you probably know there's a lot more to a person than their most widely-known accomplishment. I think a lot of people just tag Chris as the inventor of the hashtag and that's that, but he's so much more than that. He has designed products and experiences for Google and Uber. He's founded startups. He's created movements.

He's done two TEDx talks and fostered really important and beautiful relationships all over the world. He's been all over the media. He's been quoted in all kinds of things like The New York Times and Wall Street Journal. He also has done a lot of his own writing. By the way, he's also just a really cool human being, who I am so lucky to have been connected to on Twitter years ago and over those years, we've fostered a really amazing relationship and we've spoken around the world together. I'm so excited to be talking with him today. Welcome, Chris.

Thank you. Thank you so much for having me.

It's an honor to have you. When we're trying to think about what your taboo topic should be, we went all over the place because you are a person who's not afraid to have tough conversations and you've put a lot of taboo stuff out there and it's been really important. When we really landed on our topic, essentially, we came to this idea of, "Hey, I have a sex life. I have sex. I am a sexual being and I'm not afraid to talk about it." It's a complicated thing in our time as we're coming to understand privilege and power dynamics and that sex is one way in which privilege and power dynamics are played out.

There's a lot of sensitivity in people going to the opposite extreme, where they don't feel like they can even admit to themselves or others that they are a sexual being with needs and desires. Maybe, you can share to whatever extent you're comfortable, or willingly uncomfortable, about your own journey as accepting yourself as a sexual being and figuring out how to present yourself as such in a world where the messages are really mixed about what's okay and not okay.

Yeah, and I think that's still a budding aspect of my personality. In 2015, I was interviewed by CNN to talk about non-monogamy and polyamory. I like to look at that moment of myself as a caricature, as I'm sure I'll look at myself now a couple years in the future in this moment and say, "Wow, what a young idiot or babe in the woods I was." But part of it is trying to get to a place where your own relationship to sex is a healthy one and one where you can feel secure in yourself and then interact with other people from that place of security in order to help someone else feel safe in their own sexuality and to work on something together.

Again, that's not something I've always been able to do. It's relatively new, I would say, in my life. But I guess what I will say, my process has been one of maybe denying a lot of my own sexuality and repressing my own sexual desire because I grew up without the ability to trust my sexuality as a man. Sexual assault is something that is in my family and something certainly that my mom experienced and something I've experienced. Knowing that, I didn't know how as a man to trust my own self when it came to my desires. They seemed to be from an evil place or something because I didn't understand them.

And so, what I think has happened in the last several years is that I've become more willing to be curious about it. I've had partners that I think have been more open to allowing me space to explore, whether that's aggression or whether that's just intimacy and then to, I think, talk about it afterwards and then also to receive what someone might be interested in trying out or exploring. It's so important to create a safe container and I wasn't a safe container. And so, that was a process that I had to do with my myself to get true with myself like, what is it that I'm desiring right now? What am I not saying? Why am I not saying those things? If I say those things, who is really at risk?

Is it because I might get turned down and if I get turned down, well, what does that lead to? Or if I say this thing, will that hurt the other person's experience, or will they not trust me? Will they wonder or be skeptical about what's motivating this desire? It's just made me sit with those things for, I think, a lot longer and then try to observe and read and listen. Esther Perel, I think, has been transformational in learning about some of these things and learning about ways to talk about them. It's so great that there's so much that's out there now that's non-judgmental, that's non-shaming and has given me a way to develop that part, that inner language, that ability to communicate in a way that I previously couldn't.

I feel like you so beautifully talk about things in the abstract and I'm curious if-

Sure.

Could I challenge you to-

Please.

And take your time to think about this if you need to, what is a more concrete example of what this has looked like for you? Maybe, you can share a misstep or a lesson or something that you've come across that people might be able to understand your point.

Yeah, there's this one experience that I had. I think I'd gone out and maybe had some drinks or something and I wasn't thinking that hard about it. My partner texted me and we were going back and forth in this dialogue. She actually talks about sex quite publicly. She challenged me to change my Twitter bio to talk about giving her orgasms, specifically more orgasms per day than I had previously or something, to challenge myself to rise to this new occasion.

Wait, were you already giving her more orgasms than ever before, or was she asking you to put this in your bio so that you would make that your goal?

Yeah, I am forgetting the details, but what I will say is that the important thing was that I'd never really talked about sex on my social media profiles in this way. I'd done the interview with CNN and that was about non-monogamy and relationships, but that simply was about thinking differently about what monogamy is, what it means, why that one way of doing things may not be the only way that people should construct their relationships. I hadn't actually ever talked about the 'O' word or sex before quite so publicly. And so changing my bio, granted... I have a 100,000 followers. And so, if I change my bio, I don't actually think that a 100,000 people are going to see it. It's so obscure. There's so many people on social media now, that I'm just like, "Whatever."

Funny how people notice the word orgasm-

Yeah, right?

More than other words though.

Well, the funny thing about it, which I hadn't thought about, was there's a service called spoonbill or something, which I think is a type of duck. Doesn't matter. But what it does is it actually tracks the bios of people that you're following and if it makes a change, you get an email notification that says, "Hey, this person changed their bio." It's a great way to see people changing jobs and stuff like that. Of course, when my bio changed to be about giving my partner the most orgasms she's ever had, that caught some people's attention. Anyways, I changed my bio and this was, I don't know, it was midnight or something, 1:00 AM in New York. I went to bed and of course, the next morning, all these people with so many more followers were flabbergasted because the version that they knew of me, that I'd clearly been spending years constructing in their minds, suddenly broke.

It was like, people thought I'd been hacked. They thought that someone else had taken over my account. They were like, "What is going on?" That gave me this really interesting moment. One, to consider the perception that I'd created with myself and also the way in which I hadn't fully integrated this other part, and then to also realize that for all of these people that are criticizing me for talking about orgasms with my partner who challenged me to put this in my bio, the problem was so many levels deep because some people were like, "Oh, look at this asshole who's talking about wanting to have sex." "Oh, another guy who wants to have sex. Look at that. That's so unusual." But this was different. At least to me, it seemed different. And so part of it was like, "No, you don't understand."

For so much of my life, I thought sex was dangerous, something I shouldn't want, something that I should repress, something that my gender tends to use as a blunt instrument or as a type of force against other people to get power from other people. That's not what I wanted to be. And so, for me to put this out there in the world is for me to say, "Actually, I feel comfortable with this part of me. I'm not afraid of this part and I feel bad for you. If you're a guy and you see this and you're intimidated by this, or you think I'm an asshole, whatever, you have no idea." The lack of curiosity and the lack of response, specifically from tech people around saying, "Oh, that's amazing. Why don't we all get in concert in giving our partners amazing orgasms for a month?" To me suggests where there is this gap. I mean, there literally is a gap, but also a gap in the conversation.

Well, what's so complicated too is I feel like you represent tech in this really interesting way for so many people. You invented the hashtag. There's something so tech about that, I almost don't even know how to handle it. The idea of marrying tech and sex is really complicated because most of what we see in the media when you see tech and sex in the same sentence is an abuse of power or something going really wrong, or someone being really thoughtless and insensitive. I can understand the dilemma of the modern man, where it can seem unclear about how to integrate these things in a thoughtful and respectful way and knowing that there're going to be some people who are hurt and offended no matter what, because they haven't been treated with the respect that they should have been up till now.

Yeah, absolutely. I think that's even why I continue to, I don't want to say struggle, but still find it a little bit peculiar and awkward. There are some parts of my life where being able to talk about sex is the same thing as talking about the breakfast cereal that you had or something. It's just not that remarkable and it's something that everyone does. In other context, it's harder to have those conversations. People feel, "Ugh." They're like, "Oh, I don't want to talk about this," or, "Ugh." It's a problem. It's fraught because sex is such a personal thing and it's so deeply about the individual and about all the stories and experiences that they've ever had.

It's a very personal thing because certainly evolutionarily, long term, your ability to either have sex, cultivate sex, engage in sex has been part of your ability to belong and to fit in. Sex has been used in so many different ways, for better and worse, in human culture that it's so hard to take anything for granted and to make any assumptions. And so, every time you come into a conversation about sex, it's almost like you have to warm up and have an onboarding conversation to say, "Where are you at with this? How do you feel about it and how do you-"

You must need consent to have the conversation.

Yeah, frankly. You have to constantly check in.

But the other thing that's complicated about it is our society is so scared of sex and asks people to deny such natural and universal feelings all the time. My experience as a therapist has taught me that most acting out and most crime and most harmful things that people do come from some version of never having been allowed to think and feel and say things until they just come out in some crazy action. And so while starting to have these conversations feels really important, I also think having them younger and in safer places and helping people... I mean, we live in this Judaeo-Christian society where you're supposed to not even want it until you're married and it's just not how it works. And so, how do we start having these conversations in ways that make people feel safe to even look at these things in themselves?

Obviously, these are huge questions and a lot of it, I think, comes from studying history and how we get to be this way. We are the first real generation that I don't want to say takes birth control for granted, but where birth control is universally accessible. Whether it's good or bad is its own conversation, but the fact that sex is not simply done anymore just for procreation allows us to actually get into the body and to experience things that are actually biologically-driven motivators to get us to reproduce. If the best feeling that you could have as a human was to eat, we would just eat ourselves to death and then we'd fade away.

But instead, our biology has been created to give us the perception that we want to have sex, because that's the way that our reward system is built up. It's so powerful and it has to be powerful because again, we would die off if it weren't so powerful. So, you have to acknowledge who and what we are as an organic creature and then take that and put that into the context of culture and civilization. We find ourselves in this moment where we're becoming deeply electrified in a sense. We're living in technology that allows us to get exactly what we want without any concern or care or respect for the tools in which we get those things.

I'm thinking specifically about voice assistants like Alexa or Siri. You don't have to ask consent or send Siri a birthday card or things like that. We're losing some of those ways in which we can look at each other in the eye and gauge how the other person's doing and then to ask inquisitively, "How are you?" To show deep empathy and care. I think that, that's something that desperately needs to be reified in our education system, because I think what you're saying in this conversation about sex or having this conversation about sex where there's a warmup requires you to really care about someone's experience, to be as curious about all the ways in which they got to the way that they are now as the outcome that you're trying to get to.

It's like conversation foreplay.

For sure, a hundred percent.

Expecting someone to be ready for something that's ultimately a very stimulating experience before they can wrap their mind and their body around being ready to have that experience is not ultimately going to be good for anyone. But I'm curious. You have this huge reaction on Twitter from this bio change. You are out there having these conversations. What have you found has evolved as you've started to put yourself out there? In what ways do you feel more confident talking about yourself as a sexual being and person in tech, and in what ways do you feel like you still have to be a little bit careful?

I think maybe part of this shift has been just feeling less like a person in tech. A lot of people are looking for tech to make all these changes, to fix all the problems, and I fundamentally don't think the tech is going to solve any of the problems. I think that the problems are actually with the people and with the individuals. Granted, that's a much harder thing to change, but maybe I have that vantage point or perspective because of my relationship to the hashtag. It's like if I went back to 2007 and was like, "Okay, you need to convince everyone in the world to change the way that they write their words in order to create this new environment where people could have conversations across the world spontaneously in a moment's notice without ever pre-coordinating and suddenly, they're learning about things and experiences that they're having that are actually matched elsewhere," I would've been like, "Yeah, right. That's never going to happen." And then, it did.

And so if in a similar way, through conversations like this or through modeling those conversations, which is exactly what I did with a hashtag. It was like, "Here's how I think this thing could work. Let me show you." I'll just keep doing it over and over again and I'll find little moments of leverage to show people how this can be beneficial with a little bit of change on their own parts. In a similar way, I hope in the next 10 to 15 years, these conversations will lead the next generation to be able to check in with themselves, to slow themselves down, to be able to build that into their products, to be able to say, "Is this the right thing for me right now?"

Maybe, one of the big problems that we're experiencing is that tech doesn't actually have a consent model for us. It does in a sense. It's like, "Do you want to allow this app to use your location?" Right, but then you can't actually ask questions of it. What is your real intent? What are you really doing with this? If I'm going to send you nudes, who are you going to show it to? That's a big omission in our technology that we have with humans. And so, unless we have that ability within each other and the conversations that we have with each other, we're not going to build it into our software. That's where I guess I see this going in, what's changed for me. I think I used to maybe have more faith in the tech of being able to just fix things that way, and now I don't believe it anymore.

You know what I love about conversations with you, Chris? Is it's like we're on this magical ADHD journey together and I never know where we're going to end up, but I'm always down. It's always interesting. Never could have predicted it at the beginning. Since we're coming slightly to the end of things, I'm curious if we can tie it up. What would you suggest to people out there, maybe we'll even focus it on men out there, who are wanting to start being more open about themselves as sexual creatures and have these conversations while still acknowledging that, that puts others in a tough and sometimes unsafe feeling position?

Yeah. Again, I just want to check my own place in this. I'm one person developing my own story, discovering and finding things out, and I don't have all or any of the answers.

Sure.

It's evolving. I say that because I also notice that there is an aesthetic around allyship that seems to be developing as well and I honestly think that the first part, if I were to have a conversation with myself 10 years ago, the right allyship to start working on is actually allyship with yourself. There's no way for me to help someone else feel safe in my presence if I don't feel safe within my own presence. And so, a lot of that work has been like, what is driving me to want this experience right now or to want this from this other person and to be able to get really good and really intuitive about that.

And then also, I think on the one hand it's that, is recognizing, "Okay, what's motivating me to want this right now? Is it that I want them to feel a certain way, or I want me to feel a certain way? Or do I want power or do I want to feel validated? What is it?" And so, the other thing that's really important I think about is checking your own desire for a certain set of outcomes. If you can separate yourself from having any certain thing happen, I think that also is a really good way of cultivating safety within yourself because if you're not going to get disappointed, if it's okay for the other person to reject you in a conventional sense, but you don't take it as rejection, you take it as like, "Oh, look, it's raining outside. Am I angry at the sky because it got cloudy and I wanted it to be sunny?" No, it's just the way it is.

So in this moment, you might be with a partner or something like that and they're not feeling it for whatever reason, something shitty happened at work, it has nothing to do with you. If you allow them that space and their own self-sovereignty, and then to communicate it with you, when they are ready, then I imagine that they're going to be a lot more ready and willing because they know that it's safe to say, "This isn't what I want right now." I think that's the other thing that I would go back and talk to myself about. One is about being an ally with yourself, checking in with yourself, understanding what's driving your motivations. And then, the other is to lose any attachment to outcomes, to allow the other person to say, "You know what? I'm not really wanting it right now, but come back to me tomorrow or something and we'll try again," and to be totally okay with that.

Yeah. I know that this is the most broken record thing I do, but I just find it really hard to imagine this being a journey that's possible to do on your own. Because I think it's unfair to ask people around us to do it for us, that is why I believe so strongly in therapy. Find a person whose job it is to help you do this work on yourself because it's impossible to do an isolation because it's all about interpersonal dynamics anyway. If I can push one idea around all of this, it's that this journey that you're trying to go on in the world has to start with the inner work and...

I will say, I've done a lot of therapy. I had a lot of help in that sense for me to be able to play out these ideas in a context where I had that ability to investigate and to explore, to go into therapy as though they are a trainer for your mind and your emotional health, because you're going there for yourself. You're not going there to please them or to make them feel good. They're there to hold space for you to throw out a bunch of idea dice in a sense and see what comes up and then to talk about it, to put it on the table and say, "Well, why do you want that aggression? Or why are you looking to feel that way? Is there a way for you to explore those feelings in a way that's actually healthy for you and for your partner, as opposed to being imposed on the other person?" I think therapy is totally necessary for that.

For sure, and if you're doing a depth-oriented therapy, like psychodynamic, psychoanalytic therapy, there's this added layer which is this therapist trained ability to say, "I don't think you understand the way you're coming across right now," or, "Did you intend to make me feel this particular way? Because that's what's happening right now." It's this safe way to better understand the effect you're having on people around you versus expecting those who have their own needs separate from you to bear that burden. I think there's something really relieving about having that space.

Yeah. I mean, it's something that I think a lot of people actually struggle to provide to each other because it is very hard. It's very hard to not get caught up in your own reactions to what someone else might say, to your own emotional responses. What is great about a good therapist, and there's plenty that aren't so good, are those who can one, hold you accountable to the things that you say, and then to act almost like your internal monologue but with the externalized perspective to say, like you said, "Did you realize that this is what you just said? And you realize if you were on the receiving end of this, that you would probably feel this other way? Let's walk through that."

Without any shame or any judgment, just to point it out to you, "Here's the picture that I just took of you. What do you think of it?" And have that conversation as opposed to, "Well, you're really an asshole right now." That type of labeling, I think, is where so much of the conversation breaks down. And so, having that ability to just blow out to just the basics, the basic concepts. "Here's what's going on. Let's talk about it." Super useful.

Well, I love that we started at sex and ended at therapy. That's my favorite-

This was the plan.

Kind of conversation to have. The way I end every episode is I'm going to hand you a list of really personal questions and I'd like you to read them over and pick whichever one you feel okay answering. Read it out loud and answer it for everyone.

Okay. I feel like this is very cliche to admit, but actually, I've been thinking about this a lot. So, I'm just going to say it. "If you could switch bodies with someone of the opposite gender for a week, what are some things you would do?" Well, I would probably spend a lot of time masturbating because I don't have a clitoris or a vagina and I'm very curious how they work and what it feels like to have one. To have a part of your body that has 8,000 nerve innings just sounds really intense, but also really interesting. I can't twiddle my kneecap enough to get to that level of intensity. So...

Ah yes, it is a blessing and a curse, my friend. I realized too that I wrote this question in a really not sensitive way, which is, I said opposite and gender. We're actually not talking about gender. I'm talking about biological sex and opposite implies that there's only two, which I don't think is fair either. So, let me at least-

Yeah, thank-

Pull it back on that.

Thank you. I did notice that and I was like, "Well, I guess I'll take the question as written." There's a Kickstarter that I noticed recently that's for bathroom signs and what I think is so smart about it is that it's just based on the features. For example, they will have a list. "Here's a toilet. There's a urinal. There's a sink." In a similar way, you could ask that question, if you could have any other body parts that you want to try for a week-

Nice.

What would that be?

I like that. Well, this conversation has been wonderful as it always is when we chat. Thank you so much for coming down and I look forward to continuing it as we go on.

Awesome. Thank you.

Thanks, Chris.

Thanks for listening to Emotionally Fit, hosted by me, Dr. Emily Anhalt. New Taboo Tuesdays drop every other week. How did today's taboo subject land with you? Tweet your experience with the hashtag #EmotionallyFit, and follow me at @DrEmilyAnhalt. Please rate, review, follow, and share the show wherever you listen to podcasts. This podcast is produced by Coa, your gym for mental health, where you can take live, therapist-led classes online. From group sessions to therapist matchmaking, Coa will help you build your emotional fitness routine. Head to joincoa.com, that's join-c-o-a.com, to learn more, and follow us on Twitter and Instagram at @joincoa. From StudioPod Media in San Francisco, our producer is Katie Sunku Wood. Music is by Milano. Special thanks to the entire Coa crew!