I just got back from the Woodhull Sexual Freedom Summit, and… wowza, y’all. There were a lot of cute people at that event.
While some of the cuties were folks I’d never heard of before I arrived, many of them were people I’ve low-key known on social media for a while. It’s maddeningly exhilarating to meet someone IRL and find that they’re even more adorable and charming than they were on the interwebz. That pleasant surprise can throw you off your game and make you nervous – maybe even so nervous that you can barely talk to your crush, let alone flirt with them!
I definitely fell into that trap with a few people this year. So I’ve put together this little guide to flirting with your conference crush. Hopefully it helps you – and maybe it’ll even help me at the next conference that rolls around!
Pre-game. If you start flirting with someone out of nowhere at an event, they might be confused or even put off – so it’s good to get a feel for their interest level and flirting style before the event itself. Build rapport over a period of weeks or months with jokes/jibes/compliments on social media. Find excuses to slide into their DMs, if they seem down to talk to you (our social media flirting episode of The Dildorks has some great tips on this).
Use this time to gauge how receptive they might be to your flirtations. If you’re particularly crafty, you might even be able to establish what types of activities you’d be up for at the con (“I have this new paddle I haven’t gotten a chance to use yet…” “It’s been so long since I’ve been properly fingerbanged!” “I’m looking forward to some possible makeouts at the event…”). Maybe you’ll plant a seed that’ll turn into a fun hookup later on!
Check in. Boundaries and consent are vital! Conferences are professional environments for many people, so your crush might not feel entirely able to say no if they’re not into you. This makes it super-extra important that you establish clear consent for any flirting-and-more that takes place.
Meta-communication is great for this, particularly if the crowd at your con is nerdy about sex and relationships. Flirting expert Reid Mihalko often recommends asking some version of “Is this a good time to flirt with you?” or “Are you open to being flirted with right now?” and I think that’s a good approach, so long as you’re attuned to hesitant yeses that are actually no’s.
If you’re not sure how you’re being received, you can also pay attention to the length and tone of your crush’s responses: are they engaging with your flirtation and coming back with their own, or are they simply acknowledging your comments with short responses every time? When you enter a room they’re in, do they look at you, smile, walk up to you, or do they avoid you? Pay attention to cues and do your best to be respectful. All the other tips in this post will only go well for you if your crush is receptive to being flirted with; if they’re not, doing this stuff will just be creepy or even harassment.
Use social media to your advantage. Many conferences have heavy social media engagement, so it won’t look too out-of-place to throw a few swoony tweets into your con coverage (provided, of course, that you’ve been getting good signals from them, as per my previous point). Some examples of things you could tweet: “OMG, @YourCrush’s outfit today is AMAZING 😍” “I keep hearing @YourCrush’s adorable laugh during panels and it makes me so happy!” “Thrilled I got to meet @YourCrush after loving their blog for months!”
You could also try tweeting general callouts like, “I’m going to the pool/business centre/balcony; y’all are welcome to join!” or “I’ll be at [x panel] next; come sit with me!” If your crush is creepin’ you like you’re creepin’ them, they’ll probably show up to some events you’re attending – at which point you can get yo’ flirt on.
More social media tricks for con flirting: send an “It was nice to finally meet you tonight; hope I get to see more of you!” DM a little while after saying goodnight. Ask them if you can get a selfie with them at some point (provided you’re also getting selfies with other people; don’t be a creep!). If they tweet about being at a panel they’re not enjoying, or not knowing what to do next, send a reply along the lines of “We’re at [x place/event]; you’re welcome to come join!”
Sync your schedules. Don’t follow them everywhere, obviously. That’s gross; don’t do it. But if you’re getting good vibes from them, you could try inviting them to lunch, telling them about a cool panel you’re planning on attending later, or letting them know about an after-hours get-together you’ll be at.
If you’re really getting good vibes, you could try straight-up saying something like, “Hey, I feel like I haven’t gotten enough time with you at this con! Wanna [sit together at this next panel/grab coffee and chat/come look at my dildo collection in my hotel room]?” Cons are busy enough that they’ll have an easy “out” if they want to say no but don’t feel comfortable being upfront (“Ahh, sorry, I can’t, I have to [go to a different panel/go talk to my friend/take a nap]!”).
Say yes to adventure. It’s easy to get tired, overwhelmed, or nervous at cons, which might lead to you declining invitations you otherwise might like to accept. While self-care is hugely important, you should also cultivate the ability to tell when you’re so tired that more socializing would actually burn you out, versus when you’re tired but still capable of going on adventures if you push yourself a little. Ask yourself which choice will make for the better story, or which choice will make you prouder of yourself in the morning. Maybe that’s going to the loud late-night spanking party, or maybe it’s ducking out early to have drinks with just a couple people at the hotel bar.
Cons can feel like a wacky dream, full of implausible situations with implausible people. If you receive an invitation that sounds fun but a little intimidating – like “Hey, come smoke weed with us in the parking lot!” or “We’re gonna play Strip Scrabble in my hotel room; wanna come?” – don’t just write it off immediately. It might lead to flirtation you would’ve regretted passing up.
Shoot your shot. Here’s what it ultimately comes down to: a conference is a time-limited opportunity to have lovely experiences with people you rarely get to see. If you want something to happen and it hasn’t happened, you can either give up, or take some action. If you’re getting flirty vibes from your crush but neither of you has taken much initiative, and the end of the con is coming up fast, it might be time to get real and make your move.
The best approach to this is going to depend on you and your crush and what kind of people you are. However, I asked some fellow introverty blogger friends, and their opinion matched mine: I think the best way to “shoot your shot” at a con would be to send your crush a DM saying something along the lines of, “Hey! You might have noticed by now: I think you’re super cute/charming/fantastic. If you feel similarly, would you like to [make out/play/hook up] sometime before the con ends? I’d regret it if I didn’t ask. If the answer is no, I’ll totally understand and won’t be offended at all, and I’ll still think you’re great!” My blogger friends agreed that a private message is better than a public tweet or an in-person convo for this, because it gives them an opportunity to think things over and phrase their answer carefully if they need to.
Have you ever had a conference crush? Did it ever turn into more than that?
Wearing ridiculous outfits. I feel closer to my “true self” at Woodhull than I do almost anywhere else, because everyone there is chill as fuck and knows me more as my brassy online persona than the awkward wallflower I often am “in real life.” As a result, I tend to dress weirder at Woodhull than at any other time all year. Last year, I rocked 
Hanging out with sex blogger friends. Chillin’ with the #BlogSquad was absolutely the highlight of my Woodhull experience last year, and I know this year will be more of the same! I feel so loving and grateful every day to have found a crew of like-minded sex-nerdy weirdos on the interwebz, and Woodhull’s one of the only times all year when we get to hang out IRL. I can’t wait to laugh til I cry, ogle each other’s sex toy collections, make bad puns, livetweet en masse, and feel surrounded by blogger love!
Make out on a sunny hillside. Look, no summer in Toronto is complete without kissing a cutie in 
Go dancing. You can really do this year-round but there is something particularly hedonistic about summertime dancey nights: you can wear a short dress or tiny shorts, adorn your face with a healthy sprinkling of glitter, and boogie til you break a sweat. Clinton’s has frequent 
Celebrate Pride. There are certainly valid criticisms of Pride – its corporatization, its predominant focus on cis gay white men, its tumultuous relationship with 
Go on a long walk. I love exploring my city when it’s warm enough that I can do so without a coat. Podcasts or songs keep me company in my earbuds, and I go wherever my feet want to take me. Walks always calm my mind and sate my body – and I often have flashes of creative brilliance mid-walk that lead to fantastic blog posts, articles, or songs!
Journal at sunrise. I don’t know why all my thoughts feel so much more poignant and important if I have them while the sun is coming up, but they do! I like sitting on a rooftop, café patio, or hillside as the day begins and meditating in my journal about whatever’s bothering me or whatever I’m grateful for. I always feel so cleansed and productive afterward.
Wear high heels. I normally hate doing this, but hey, summer is the time for it. Even if I just end up gallivanting to the corner store or local café in my 
Get together with old friends. I have several pals who go to school in other cities but come back into town each summer, and I love catching up with them when I can. We go see improv shows or outdoor theatre productions, get dinner or drinks, and reminisce about old times. It always feels so necessary and uplifting!
I continued Suz’s spanking on the adorable little pink bed in this room, alternating between a wooden hairbrush and a paddle carved in the shape of a bear. Conveniently, there was even a pink footstool for her to rest her knees on. The creators of this space have truly thought of everything!
We cuffed Suz to the Saint Andrew’s cross in this room and then proceeded to beat her up in several different evil ways. Taylor hit her chest with the aforementioned flogger gloves, I flogged and whipped her with other implements from around the room, and then I scratched “BAD GIRL” onto her pale chest with some metal talons Taylor had brought along. Hey, when you’ve got a cute sub consensually chained to a cross, you make good use of that opportunity!
