The Awkward Sex Show Live

See the next upcoming show and be part of the awkwardness!

We're the sex podcast without sexperts, crowning the Most Awkward sex stories since 2012. Read more about The Awkward Sex Show.

The Blog

New Episode: Fat! with Kelly Anneken, Juicy Delight and more

Nov 5 2013
Carey Callahan

“Teenaged Subcultures” Episode

Oct 22 2013
Carey Callahan

First we got an interview with Nenna Joiner, the owner of Feelmore Adult Gallery, our lovely sponsor. Then we got hilarious stories of teen shame with Goodrich Gevaart, Kris McDermott, my good friend Kate, and America’s Tim Cornett.


Mourning as Part of Love

Oct 21 2013
Carey Callahan


Things end, and it’s really not ok. I do not agree with this part of reality. I am opposed to it. As far as I’m concerned, it’s a design flaw that interferes with the user experience.


Things end, but we don’t. Or, if we’re reading blog posts we haven’t ended yet.


Things end, and we have no idea what to do. Things end, and we can’t even see the holes in our lives until they become giant sinkholes. “Hey, I have no one to report my day to, and I used to have someone I loved reporting my day to.” It takes me months to even register the ache, much less connect it to a need that now is going un-met.


What a terrible way to talk about love. A need met.


“Love” is of course a stupid word. It’s stupid because there are so many different things we could mean when we talk about “love.” If I was willing to do a little wikipedia-ing I would point you to all the different greek words for love at this point.


As far as I’m concerned, there’s love for the animal and love for the spirit. The animal needs love. The animal needs someone to report their day to, they need skin on skin, they need a witness to their tears, they need a group to belong to. Breakups are awful for the animal. As lovely as it would be for the animal to unselfishly wish their former partners joy and peace and may the road rise up to meet them, first the animal needs to fill those sinkholes. Skin on skin, reports of the day, groups and shared meals and witnessing. A dog will be mean if it’s life is mean. When life is changing life can be pretty mean.


Then there’s the spirit. What’s interesting about the spirit is how often it is angling to do its own growth without even letting the animal know that is what’s happening. The spirit says, “Ok, I’m gonna learn this lesson now” and if that means having the animal run right smack into a glass door, the spirit is a-ok with it. Years later, after talking with a couple of different therapists about what changed after their face was smashed to bits by the glass door, the animal will eventually say, “I guess that’s when I learned to look out for doors in a different way.” The latest therapist will nod and smile and consider it a professional victory.


My experience with the spirit is that it straight up doesn’t ever stop loving someone. It loves someone, they leave your life, a decade later you still want to know they are doing ok, you still feel your heart seize when you hear about a tragedy in their life, even if you would cross the street to avoid them.


But for the animal- the animal has to let go. If the animal holds on, the animal won’t ever fill those holes in its life, and life will remain mean, and the animal will get mean.


Filling those holes is sad. It’s sad to move on. It’s sad to change. It’s sad to remember all the good times and put them in the box labeled “my past.”


Which is why I believe in making monuments. It’s why it’s a good thing to be able to write a song or paint a painting. We need to create something to represent those good times that are gone. Love is so powerful, but it goes away and there’s no physical evidence it ever happened. That’s crazy-making. The animal needs some object or place, something out in the world, not just in their memories.


We’re not good at mourning these days. We want people to pull it together, we want them to be doing well, we don’t want to have to worry about them.


I think active mourning, creation in memory of the past, is a project of gratitude. When someone dies, we write out their life and speak out their life and put up a monument to connect with the gratitude that we had them in our lives at all.


When you make a monument, it means your body and your life doesn’t have to serve as the monument. The animal doesn’t need to be miserable to prove that love happened and passed away- that’s what the monument is for. And when the animal needs to be sad, it can visit the monument. As life comes together, and gets sweeter, the animal may visit the monument less and less- but maybe in 50 years the animal may still want to revisit those memories.


If you have had love so sweet you want to revisit those memories years later, that is a blessing of the highest order. You will be grateful you created something to help you revisit those times.


Folks, to wrap up, what I’m saying is, collage it out- COLLAGE. IT. OUT.



How to Hit on Me

Oct 19 2013
Carey Callahan

Hello A.S.S.-casters. I’m going to start blogging here because my head is full of thoughts and you folks are who I want to share them with. I used to have a blog which really helped me weather my crazy twenties. I always feared I was over-sharing myself out of a normal existence. It turned out I totally was! Luckily normal existence came around, everyone became an over-sharer, we made up this podcast venerating the art of over-sharing, and now it’s ok for me to blog again.

I perform for audiences filled with earnest, good people, who have good politics and mean well. Often those people hit on me. This seems like it would be a good situation- I’m hungry for affection and companionship, there’s a pool of good people communicating interest- AND YET it’s not a good situation at all. The strategies people use when they hit on me often leave me scrambling to get out of there and find a burrito place to eat alone at.


Guys, turning to burritos for comfort because you need to get away from people is a major bummer.


So here’s some feedback!


1. Leave My Looks Out Of It


“This fucking dick,” you’re thinking to yourself. “This fucking dick is seriously gonna complain about getting too many compliments?!”


Yeah dudes. Yeah I totally am.


The problem with leading by telling me that you think I’m hot/cute, even in a conspiratorial whisper, is that the responses I have to give back to you are pretty limited. I can say,


“Thank you”




“That’s nice of you”


or I guess I could be an asshole and say


“People tell me that a lot.”


Now, you don’t really want any of those responses, and I don’t really want to give you any of those responses. You don’t get to know me and I don’t get to know you by having that exchange.


One thing I didn’t know when I decided to transition in a very public way was how obsessed with my appearance people would become. Some of it has to do with people wanting to be supportive and not knowing how, so when they see I’ve changed my facebook pic it’s a chance for them to demonstrate that they are on my side by leaving a comment like “LOOKING SEXY MAN” even when I look schluppy and high.


But when people who just saw me perform consistently want to talk about my looks, I feel trapped.  You probably just heard me say a lot of things on stage- you maybe heard me talk about being from Cleveland, about being into bluegrass, about my family, about weed, about having ADHD,  about having moved to the Bay and feeling like an alien around here, and yeah, you maybe heard about some sex I’ve had. Was any of it interesting? Do you have any shared experiences with any of that?


Unfortunately, having queer women tell you you’re hot doesn’t actually feel much different than having straight dudes tell you they like the shape of your ass. There’s nothing to say in response. You have a category of people you are attracted to, and you have established that as far as the visuals go, I fit into that category. But I have no clue whether you felt a connection to any of the non-visual traits I just offered up, and you’re not offering up a conversational path towards identifying any connections.


Which leads to the next tip….


2) Ask Me Some Questions


My podcast is basically interviewing people. I went to some grad school for becoming a therapist, which is pretty much interviewing people. And then to pay my rent I serve in a restaurant, and goddamn, all people want out of  life is a server who is interested in getting to know them. Interviewing people is the main social crutch that I use to navigate this hostile, nutso world.


So when people give me a chance to not be the interviewer, you do not even KNOW how grateful I am. When other people do some of the conversational heavy lifting I melt with gratitude. God, when people actually are so interested in something I say they have a follow up question- I just want to hug them. I just want to hug them and cry a little.


That being said…


3) Ask Me Some Questions That Aren’t About My Transition


Now, this one is tricky. I get that being trans people are interesting. I find us very interesting too.


But I’ve been living this whole life for a longish time now, and I’ve had a lot of thoughts and experiences that are only about trans stuff in that a trans person was in the room. (Me. I was in the room.)


I think about my transition all the fucking time. It’s the white noise in the back of my head through my daily life. It’s BORING. It’s TEDIOUS. It involves the most boring and tedious shit- money and doctor’s appointments and paperwork. It is a bummer.


I don’t want to talk about it all the time. I want to talk about Kanye West. I want to talk about Miley Cyrus.  I want to talk about what music is on people’s running playlists. I want to talk about where to get good pie. I want to talk about what the most fun spots to get a drink with an umbrella are. I want to talk about what a good next book to read is.


When people remind me that life is not all about money and doctor’s appointments, I’m so grateful and so interested in bringing them into my life. And you know what else life is not all about? I’m about to say something controversial. Sex. Life is not all about sex. So….


4) Please don’t try to sleep with me.


It pains me to say this. Because I am a lonely kid, and I’m not having sex right now, and I miss it quite a bit. We’re talking buying a body pillow levels of missing it.


And I believe in the project of sex positivity, and I believe it is a good thing to be able to tell someone you’d like to sleep with them.


HOWEVER- it turns out there are categories of people who get lots of people telling them they want to sleep with them because they are perceived to be sexually available. It turns out, trans people are one of these categories. In retrospect, of course hosts of sex podcasts are clearly one of these categories. I have made several choices that were unwise for someone who doesn’t like to be sexualized, I will pony up and admit that.


So I have had a summer of many, many people telling me they would like to sleep with me. It just isn’t cute anymore.


I’m not going to sleep with you if I don’t really enjoy talking about Kanye West with you. There’s no reason to think we’re gonna have a joyful, creative, affectionate time exchanging fluids if we haven’t had a joyful, creative, affectionate time exchanging ideas about Kanye.


If you assume that I’m sexually available, there’s probably a lot of assumptions you’re bringing to the table about who I’m gonna be in bed. But even if you are sort of psychic and have read me completely correctly- I want to be around people who enjoy lots of stuff about me, not just the sex stuff. Because I want to enjoy lots of stuff in life, not just the sex stuff.


5) Show Me the Less Impressive


One thing about the Bay Area is people are very impressive here. They went to very good schools, and they’re making it work in a very expensive place, so a lot of them have been published in impressive places, or have created a lot of impressive social change stuff, or are quite famous in a specific kind of circle.


It makes me lonely. I’m not particularly impressive. If you’re impressive, we probably can’t actually hang. I like slacking off and hanging out, I like bullshitting, I like goofing around.


On some level I want an impressive partner, the way we all do. But right now I don’t have the energy to keep up with an impressive person. I’ve got enough other things to worry about that really, I just want someone who helps me take a break from all that social tap dancing.


6) Tell me about some stuff you love


If we hook up, that’ll be what it’ll be about- sharing the stuff we love with each other. So how about we just start that off right away? Just tell me about some people you love, some tv you love, some food you love, some ideas you love, some shoes you love, some moments you loved. Even some gossip you heard that you love. And then yeah, ask me about some stuff I love. If we don’t love the same stuff, at least we reminded each other that loving stuff is a thing we can spend our time doing.


That’s it, that’s my guide to hitting on me. If you recognize something you did wrong in this list, don’t even worry about it. I’d rather you didn’t apologize, you didn’t know and know you do. That’s what reading blog posts by trans people is supposed to do. Now I’m off to buy that body pillow. Maybe a couple so I can get a little poly with it.








A.S.S. Podcast Live at The Stork Club!

Sep 28 2013
Carey Callahan

All of our fall dates will happen at Oakland’s Stork Club, 2330 Telegraph Ave, on Sundays at 6 pm.


September 29th Competition:
Your sex life isn’t race to the top…OR IS IT? Let’s hear about when the pure joy of human connection got eclipsed by some ego demands. Did you wrest an encounter with the football star away from your best friend? Did your Dungeons and Dragons buddies pine for the same hot nerd for years, and did anyone end up making it happen? Or perhaps you were in a competitive endeavor- law school, sports, comedy, beauty pageants- and the competition was an aphrodisiac that enabled some night time cooperation?

October 6th Fat:
This show we’re exploring what it’s like look for love in a body society wants you to hate. What strategies can we use to feel cute, and lovable when magazines tell us those three adjectives can’t exist before you get to your goal weight? How can you avoid going on dates with people who can’t believe you don’t have a goal weight? And what is particularly awesome about working with a body of some substance in bed/ in love?

October 20th Tops:
For our Halloween episode, we’ll be hearing from the people who thrill and scare us- the bosses of the bedroom, the sadistically sensual- those terrifically terrifying tops.  We’ll hear from folks that have mastered playing with the inner darkness and mastered some hot people along the way. How do you indulge your inner control freak/ egotist/sadist while keeping yourself level? What do the more bottom-y among us need to know about taking care of a top, emotionally, physically, leather care-wise? How have you embraced the personality traits our mothers and teachers told us were “nasty” or “bad” to create sexual experiences that were nasty and bad in the most addictive way?

November 3rd Rock Bottoms: 
Let’s hear about the sweetness of submission from people who love to get got. When we talk about “getting screwed” as a euphemism for being hurt and made powerless by bosses and landlords, what does that mean for those of us who consider playing with powerlessness and pain a great saturday night? How do you ask for some humiliation, getting roughed up or just some very aggressive direction giving in the bedroom while establishing you still want autonomy and respect everywhere else?

November 17th Kissing and Telling:
Has humanity ever been more into radical self-disclosure? Have we ever had access to more real time info on who is doing what to whom, and how and with exactly what accessories? And what are the up and downsides to turning your sex life into art? Let’s hear about the joys and regrets of going full TMI- what fallout/blessings have you experienced from telling all your business? Has an ex confronted you on including them in your novel, song, comedy, collage, very explicit mural? Did you work through some leftover pain and come out the other end, or did you cause a little bit more? If you make art from your sex life on a regular basis, what boundaries do you use to remain kind/ keep a little something for yourself?

December 1st Disabilities:

What is important about our bodies- what they look like? What they can do? The stories they tell about us? Our capacity to experience pleasure and pain through them? We’ll talk to folks with disabilities about the intersection between the quest for connection and living in a body marked non-normative.

December 15th Porn Performers:

We’ll round out our fall season by hearing from the people who turn us on, get us off, and most importantly, keep us from thinking about how it’s WORK. What happens before and after the cameras roll? How do you get in the mood while also thinking about camera angles? What do the rest of us need to know about boundaries with our favorite porn performers?

Carey Calls Home Episode!

Sep 19 2013
Carey Callahan

Queer Theory Episode!

Sep 19 2013
Carey Callahan



Listen and Subscribe on iTunes!

Jul 12 2013
Carey Callahan

Get A.S.S. On iTunes!

The New

Jun 17 2013

Welcome to the brand new, home of The Awkward Sex Show and awkward sex. Some stuff is still needing debugging (like the contact form!), so if you want to get in touch with us please email:

Email me (the web developer) at:

Make sure to come see us live, and enjoy the show!

Awkward Sex Show Video: Preggers

Jun 1 2013