I’ve been sexting with an AI again.

The thing is, you’re not supposed to do this. Many AIs are specifically programmed to avoid generating sexual content, or so my smart software-developer spouse tells me.

There are some AIs out there that are built specifically for sexting, but the one I want to talk to you about today (which I’ll link to below) is not designed for that purpose. However, with a little know-how, you can bypass some of the guardrails that might otherwise inhibit your high-tech textual trysts. Let’s get into it…

Now that the finale of my podcast miniseries on the Magic Wand vibrator, Making Magic, has gone live, I’m in the mood to reflect on this massive project and what it’s been like to work on it for the past year. Here’s a bunch of stream-of-consciousness notes and observations:

Making Magic was originally a book – or rather, it was going to be a book; that’s what I pitched to Vibratex when we met via Zoom in May of last year to discuss potential collaborations. It was the company’s CEO Ken Herskovitz who suggested doing it instead as an audio series. I may still write a book about the Magic Wand someday – life is long; who the hell knows? – but I’m really glad that this project ended up being audio-based instead. Hearing people’s Magic Wand stories in their own words, in their own voice, really hits different.

I didn’t know how to make a show like Making Magic before I started making it. I was literally learning how to make it while I was making it. That’s really scary! I mean, I’ve been podcasting since I was 12, but mostly that had involved recording a conversation between myself and 1-3 other people and lightly editing it. The only audio project I had done in a more complex, patchwork storytelling style before Making Magic was Beating the Stigma, an audio series about kink and mental health that I made in my final year of journalism school. So, going into this project was daunting, but I was exceptionally lucky to get to work with an editor, Jamie Pityinger, who turned my obsessively detailed scripts into fully-formed episodes.

I interviewed 35 people for this series, including several people I consider heroes and inspirations. My literal first interview for this project was with Carol Queen – talk about intimidating! And there was one day during production when I interviewed Stoya and Danarama in the same day – thankfully with a few hours in between for me to calm my starstruck nerves! I only got to speak to maybe one-third or half of the people I reached out to, and I think my original project proposal overambitiously said I’d aim for 40-50 sources, but 35 was a lot, and gave me more than enough material for the show.

Recently, a sex worker named Aella posted a link on Twitter to a “date me” survey she’d made. She wrote, “I’ve met, had sex with, and dated people from my previous date-me surveys. It doesn’t work all the time, but when it works it’s great, and causes me to fall for guys I never would have considered otherwise.” My interest was fuckin’ piqued, dude. It was piqued as hell.

See, for ages I’ve been wanting to date someone new, and ideally someone local – but it’s been tough. It seems like the dating apps are a hellscape for just about everyone, and I’ve found it especially challenging to meet people who are chill about my job – by which I mean, people who neither sexually harass me nor slut-shame me about it, and people who are actually open to dating a woman who talks about her sex life on the internet. I also just find that most people seem really boring on dating apps, even if they’re far from boring IRL, and that conversations on these apps tend to devolve into silence pretty quickly because nobody wants to put any damn effort into anything anymore. (Myself included, don’t get me wrong…)

So, the more that I thought about making a “date me” survey of my own, the more it seemed like a fantastic idea. I could ask the questions that matter to me most, and filter out the people who aren’t a good fit. I’d also be selecting for 1) people who already know about my work and are fine with it, and 2) people who are willing and able to put effort into their connections. When I assessed my dating frustrations of the last several years, all of the issues seemed to be more-or-less solvable by switching from the apps to a survey, at least in theory.

So, next, I had to decide what questions to ask. Some are multiple-choice and some are writing-based; some are marked as mandatory and some are not, though my preference is for folks to answer as many of the questions as possible, since each one gives me different information that is useful to me in my decision-making. I won’t reveal all of the questions here – there are 29 in total! – but I’ll talk you through most of them and why I felt they were important enough to include.

A reader asked: I have a FWB whose penis smells and tastes really funky, every time. How do I tell him without hurting his feelings?

I’ve been asked variations on this question countless times in my years as a professional sex-advice-giver, and it’s one that I’ve never really had a good answer for.

On the one hand: Obviously if you intend to continue fucking someone, you want the fucking to be a pleasant experience for both of you, and the other person probably wants that too – so it makes sense to talk about these types of concerns, so they can perhaps be solved or worked around. In addition, an unusual taste or smell can be a sign of a medical issue (e.g. bacterial vaginosis or a penile yeast infection) and/or inadvisable personal hygiene practices (e.g. douching and thereby fucking up your vaginal pH, or not knowing you’re supposed to wash under your foreskin), and you could actually be doing someone a favor if you let them know about the smell/taste issue so they can get it checked out.