How to Flirt With Your Conference Crush

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?

How to Reply to Women on Twitter Without Disgracing Your Entire Gender: A Guide for Dudes

Being a woman on Twitter guarantees some level of harassment. That’s doubly true if you’re a woman who tweets about sex.

I created this post for two reasons: a) for the benefit of dudes who badly need this kind of instruction, and b) as a resource for women to send to douchebags on Twitter (and in other mediums, too, if they feel it’s useful in other contexts).

For that latter reason, I’ve put some page-jump codes into this post so that you can send dudes the link to the specific rule they’ve neglected to follow. Here are those links for easy sharing: Don’t mansplain, don’t answer questions no one has asked, don’t reply when a favorite would suffice, don’t favorite too many tweets, don’t be redundant, make valuable contributions, pay attention to context, read before you respond, don’t ask for pics, don’t oversexualize, don’t explain someone’s joke to her, accept you might be wrong, don’t demand anything, don’t tweet an email-sized query, proofread your tweet, and be generally respectful.

Without further ado… Here are my dos and don’ts for dudes on Twitter. These rules aren’t hard to follow, and yet you’d be shocked how many people break ’em.

Avoid mansplanation. Don’t explain things to women as if you know more than them, unless they’ve actually asked for an explanation or advice. Especially don’t explain women’s own experiences, ideas, and bodies to them – we’d know better than you would. Not sure if you’re mansplaining or not? Words like “actually” can be a tip-off.

Don’t answer a question that no one has asked. If I wanted to hear about your dick, your preferences in women, or what you think I should wear (or not wear), I would ask.

If your comment can be expressed by favoriting their tweet, do that instead. You probably don’t need to express your approval in multiple different ways. Favorite, or reply, or retweet. Don’t do a zillion things.

…But don’t go overboard with favoriting. Please don’t be the dude who combs through all my selfies and favorites all the sexual ones in a row. That’s just gross. Back off, dude, your inappropriate boner is showing.

Make sure what you’re saying hasn’t been said by someone else (including the woman you’re tweeting at). Redundancy is boring and not useful. You’re probably not as original and brilliant as you think you are. Especially don’t repeat a woman’s exact point in different words. If you desperately need to express your agreement, see above re: favoriting and retweeting.

Make sure what you’re saying is valuable, relevant, and actually contributes something to the conversation. Don’t just shove yourself into my day for no reason. If you don’t have anything particularly useful, interesting, or new to say, then you don’t need to say anything.

Stay aware of context. If you’re confused by someone’s tweet, flick through her previous tweets, bio, recent blog posts, etc. for possible clarification before you ask her about it. Please don’t be that idiot who has no idea what’s going on. And along those same lines…

Before tweeting about a blog post or link, actually read said blog post or link. I guarantee you, you will come across as a buffoon if you neglect to do this. If you haven’t read a post, you aren’t equipped to write about it, even on Twitter.

Avoid any and all variations of “Pics or it didn’t happen.” If a woman wanted to post a picture, she would do it. Asking for photos of her outfit, face, body, or anything else can come off as intensely creepy and inappropriate. Don’t do it.

Don’t make everything about sex. I know it’s hard for some dudes to get this through their heads, but even people who are openly sexual and sex-positive (e.g. sex bloggers) don’t want every interaction to be lascivious. Use your social intelligence (or if you don’t have any, get off Twitter until you do!) to figure out when a flirty response is appropriate (hint: very, very rarely) – and if in doubt, keep things respectful or just don’t reply at all.

Don’t explain a woman’s own joke to her. It’s surprising and strange how often this happens. It’s like some men don’t comprehend that women are actually capable of being funny, and so they assume that the jokes we make on Twitter are actually serious statements or we just don’t “get” that we’ve “accidentally” made a pun or joke. Assume we are brilliantly funny babes who know exactly how clever we are, and go from there.

Accept that you might be wrong. Exercise humility accordingly. I’m not sure if it’s due to systemic male privilege, or the argumentative nature of the internet, or cultural misogyny, or all of the above, but plenty of men on Twitter have the tendency to believe that they know best and that it’s their job to school other people. Practice saying (and typing!) the words, “You’re right. I’m sorry.” Use them when you need to – which might be more often than you think.

Don’t demand anything. Don’t ask us questions if you can find the answer on Google or elsewhere. Don’t ask us for “proof” of what we’re saying, especially if it’s something unprovable like a matter of personal experience. Don’t start sentences with “You have to.” In general, please remember: you are not entitled to our time or attention.

If your tweet requires a response longer than 140 characters, send it via email instead. Please don’t ask me a barrage of questions on Twitter and expect me to respond instantaneously, or at all. Seek out my email address and contact me there. It’s not hard – most folks will have theirs listed on their website, to which their Twitter profile will link. If you can’t find their email, tweet at them to ask for it, and be gracious if they decline to give it to you.

Proofread your tweet. I can guarantee that I will mock you if your tweet is riddled with errors. Also sometimes typos or autocorrect problems can make it impossible for me to understand what you were actually trying to say. If you care enough to type a tweet, you should care enough to make sure your message will be received and understood.

Just generally: be respectful, polite, and a decent fucking human being. It’s not that hard. If you don’t think you can follow these simple rules, a quick solution is to disable your Twitter account!

Anything I missed? What have you always wanted to tell dudes on Twitter? Got any horror stories to share?

How to Give a Killer Compliment

Giving good compliments is a vastly underrated superpower.

Talk to someone calculating, cunning, and cold, and they’ll tell you all about the manipulative powers of compliments – how you can use them to get someone in your sway.

That may be true, but that’s not what I mean when I call compliments a superpower. What I mean is that you have the power to turn someone’s day around. Maybe even to turn their life around.

Here’s how I know that’s true: I can track the evolution of my self-esteem by what compliments I received and when. The first boy to call me “pretty” when I was 12. The older man who told me I had a cute philtrum at 14. The freshman-year girlfriend who called one of my Facebook selfies “scintillating.” The sophomore-year FWB who raved about how soft my labia felt in her mouth. The senior-year boyfriend who called my dorky honesty “sexy.” The college boyfriend who went on and on (and on and on!) about my soft skin, handjob skillz, and on-point winged eyeliner.

(Ooooof. I am glowing with happiness just from writing those out! See what I mean about the power of compliments?)

Self-love gurus will tell you self-acceptance comes from within, and I think that’s true – there were times when I just wasn’t in the right headspace to hear, accept, and digest compliments. But I think a well-timed compliment, given with love and by the right person, can give you the shove you need on your journey toward self-love. That’s definitely how it worked for me.

Here are some tips on how to give a compliment that can literally change someone’s life…

Be genuine.

This should go without saying, and yet, it’s important enough that I have to say it. If you compliment someone, make sure you mean it! I’m sure you can find something about practically anyone that you like enough to compliment them on, even if it’s just their shoes or the way they pronounce a certain word.

Pay attention to what they put effort into.

I promise you, you will absolutely make someone’s day if you notice something about them that they evidently care about and then compliment them on it.

It might be physical: their perfectly-blended eyeshadow, color-coordinated outfit, or spiffy new haircut. It might be an aspect of their personality: their bravery, intelligence, humor. It might be something they do particularly well: playing guitar, baking brownies, or maintaining a flawlessly curated Pinterest page.

Notice this stuff. Say something about it. Let them see that their efforts have been appreciated.

Compliment what’s rarely complimented.

I learned this trick because I grew up smart but plain-looking, and I had a friend who was beautiful but only got average grades. She was constantly told how pretty she was, and it eventually made her doubt herself in other areas (intelligence, humor, etc). By contrast, I was frequently praised for being clever, which made me wonder if I was unimaginably hideous. What other explanation could there be?

While making sure to remain genuine, look for something that your complimentee probably doesn’t get praised for very often. Something other people tend to gloss over, ignore, or just don’t see.

Use unusual words.

A few reasons for this:

1. Your compliment will seem more genuine, intentional, and thought-out if your language isn’t generic. It shows that you had to actually scan your brain and select the best word from a number of different possibilities, instead of reaching for what came easiest.

2. Weird and wacky language is more memorable. You want your complimentee to remember your comment for days, weeks, months, or even years, instead of just forgetting it the moment they say “Thank you.” So choose words that will stick in their head (in a good way!).

3. The way our brains work, we actually absorb information better if it’s given to us in a way that requires a little mental effort. Words like “beautiful” and “amazing” are thrown out so often that we barely hear them or process them. A rarer word requires additional processing and is therefore likelier to sink in.

Instead of “beautiful,” try “radiant,” “dazzling,” or “foxy.”

Instead of “great” (as in, great shoes, great hair, great outfit!), try “exquisite,” “groovy,” or “magnificent.”

Instead of “sexy” or “hot,” try “ravishing,” “captivating,” or “delectable”!

And don’t forget to throw some strange adverbs in there. “Very,” “incredibly” and “totally” can be replaced with words like “astonishingly,” “strikingly” and “exceptionally”! (If this kind of language feels too formal/fancy for you, I can personally attest to the effectiveness of “hella” as a pre-compliment adverb.)

Let go of expectations.

It’s suuuuper annoying when someone compliments you and then just stares at you, like they want you to… what? Compliment them back? Deny the truth of what they said? Confess your love and elope with them to Paris?

Please don’t ever make someone feel like they owe you something in exchange for your compliment. A “thank you” is pretty much all you’re owed – maybe not even that. (Some people have been socialized in such a way that it’s hard for them to say “thank you” when they’re complimented, so they might deny what you’ve said. Please don’t argue with them too much. There are social and psychological reasons why they do this – and your compliment likely lifted their mood even if they don’t act like it.)

What’s the best compliment you’ve ever received?

10 Easy Ways to Make Yourself More Attractive

I think we’d all like to be a little hotter. It doesn’t have to be about other people’s approval or attention; sometimes you just wanna feel foxy, for your own benefit. Or sometimes your confidence needs a boost so you do want to attract external attention.

Whatever your reasons are – and it’s no one’s place to judge, so don’t let them – here are ten simple ways to make yourself cuter, more appealing, more intriguing. Go get ‘em, tiger.

1. Stand up straight. Check your posture in a mirror. Don’t slouch. Hold your head centered and straight on top of your neck. Practice with books balanced on your head like a debutante in an old novel if you have to. Do regular check-ins throughout the day to see if you’ve maintained your posture goals. Eventually it’ll become second nature.

2. Smile. I have resting bitchface and so do a lot of people. I get it: it feels unnatural to walk around with a smile on your face. But it doesn’t have to be a massive grin, don’t worry. Just let a small smile play around the corners of your mouth when you’re out and about. This isn’t one of those “You’re obligated to smile because some dude on the street told you to” sort of things – it’s something you can do for yourself, if you want. A slight smile makes you seem more open, cheerful, relaxed, and approachable. If that’s an effect you want to achieve, give it a try.

3. Open up your body language. Quit crossing your arms. Roll your shoulders out and back. Look around you confidently instead of staring at your phone. Take big, easy strides. Fully face the people you talk to, and make good eye contact. Let your body be a billboard bearing this message: “I’m easygoing, friendly, and open to getting to know you!”

4. Cultivate passion. There are already things you’re passionate about; don’t be afraid to talk about them. And if nothing comes to mind (?!), find something to love boldly and deeply. Books, music, theatre, art, history, stationery, sex toys, sharks, woodworking, fitness, storm patterns, architecture, arboriculture, whatever. There are few things hotter than seeing someone’s eyes light up as they talk about something they love.

5. Wear clothes that fit you. Get some stuff tailored if you need to (and you probably do). Get rid of anything unsalvageably baggy or tight. (If you’re the type who holds onto clothes in the hopes of one day being able to fit into them, fuck that – live your life now, not later.) Put on a belt. Cinch your waist with a jacket or cardigan. Get your pants taken up so they don’t drag on the ground. You’ll feel so much more capable and confident when your clothes complement your body instead of hiding it or squeezing it.

6. Speak with conviction. Don’t be a mumbler! Speak clearly and at a volume that’s definitely audible but situationally appropriate (no yelling in the library, please). Say each word like you chose it specifically and carefully. Try to eliminate transitional, buying-for-time words and phrases such as “like” and “you know” and “um” (but don’t beat yourself up about it, because it’s hard). If swearing makes you feel tacky, give it up; if swearing makes you feel boss and badass, go right on ahead. Believe that your words and ideas are important and speak them accordingly.

7. Stay informed. Follow the news. Keep up with culture (the parts that you like). Learn new words. Read. Form educated opinions on things. You don’t have to be a genius, but some level of intelligence and awareness is almost universally smokin’ hot.

8. Do stuff. Get out into the world. Meet people, go on adventures, have experiences. Learn new skills, try new things, visit new places (in your city or in the world). Sitting at home and surfing the internet every night is incredibly fun and relaxing (I’m a geeky introvert; I get it) but it leaves you with not much to talk about and not much experience to draw from. Like Sarah Dopp says: “Make at least some choices based on what will make for the better story.” People who do lots of stuff are generally more interesting than people who don’t do much.

9. Improve your conversational skills. Read Dale Carnegie’s book and any materials you can find on active listening. Ask people about themselves. Come up with some interesting questions you can ask just about anyone, like “What are you passionate about?” and “What’s the last book you read?” and “What are your goals?” and really listen to what people say in response. Join the social skills subreddit for some extra help and support. Practice coming up with follow-up questions for when people tell you stories or mention things in passing, like “What did you think of that?” or “How did that go?” or “If you could do that over again, would you do it differently?” Try to remember what people have told you about themselves before, and bring it up the next time you see them: “So what ended up happening with your mom’s art show/your dog’s vet appointment/your job interview?” To state all this more simply: ask people about themselves and be genuinely interested.

10. Work on your self-love. I’ve written about this before, so have a read through that. I still wholeheartedly recommend writing or speaking positive affirmations about yourself on the daily and looking at Gala Darling’s writings on “radical self-love”. Phase haters out of your life, both the kind who hate on you and the kind who hate on people in general (e.g. tabloid magazines, YouTube commenters, overly negative friends). Remind yourself of your value daily, even if that means you have to shove your insecurities to the back of your brain in order to shine a little light on what you’re most proud of. Always always always remember that hotness is subjective, so even if you don’t like what you see in the mirror, there are plenty of folks who would – even if that seems absurd to you, trust me, it’s true, it’s true, it’s true.

What else can a person do to make themselves hotter/cuter/more likeable?