DI-SexY: Flirting 101 for Awkward People

Our new series DI-SexY leads us through Valentine’s Day and beyond with sizzling insider secrets about sexy new skills to try out. Each week, we’ll serve up a new and intriguing topic for you with tips from the pros and enough basics to get you started. Although we’ve timed it for Valentine’s Day (no surprise, a busy time for us!) the topics were chosen to make you feel amazing any time of the year and regardless of whether you have a partner, and to work for people of all genders, orientations, and relationship statuses. Check out our previous posts, about stripping for your lover (or yourself), taking sexy selfies and boudoir photos, talking dirty and writing lust letters, and giving your lover a sensual massage.

After a year of pandemic, with the end of winter and the end of quarantine tantalizingly in sight, who isn’t ready to get out and play again?

…and raise your hand if you feel like you’ve forgotten how to talk to other people. Yep, that’s what I thought—there’s a lot of us!

Of course, COVID isn’t entirely to blame for anxiety about flirting. Even in the Before Times, it was pretty normal if the thought of flirting with that cute human made you feel like a terrifying dork, or if you went into panic-paralysis over the “are they into me or just being nice to me?” dilemma.

So let’s do something about that, shall we? Flirting has an undeserved reputation for being difficult and elusive, something that only those lucky few born with silky-smooth game ever master. I’m here to tell you that it’s a skill like any other, and one that’s a lot easier and more fun than you ever imagined possible.

I know it is, because I learned it, once upon a time. I’m a veteran flirt, an enthusiast who’s done it every chance I got since I knew the meaning of the word, and who’s taught others to do it too. I was a dorky kid—glasses, braces, nerdy classes, absolutely no chill about my passions—but I dreamed of being a world-class seductress, a coquette extraordinaire who could bring a room to its knees. So I did what any young nerd does: I studied. HARD. I literally bought books that promised to teach me flirting technique. I studied breathless banter scenes in movies, catalogued the body language of people famous for dazzling others. I practiced every time I had the chance, and to my delight, people’s responses told me it was working. Granted, I’m an extrovert who thrives on social interaction, but I’ve known die-hard introverts who also had the power to leave me twitterpated, so I firmly believe it’s something most people can get at least a little bit good at.

What IS flirting, anyway?

My definition of flirting is incredibly simple: It’s the art of making someone else feel like the most fascinating person in the world while you’re interacting with them.

What’s important in that statement is not what’s in it, but what’s not in it.

• It doesn’t require the other person to be interested in you or to behave any particular way
• It’s not something you’re doing with any expectations about what you’ll get out of it
• It’s not specifically sexual (flirting can be very sexy, but in a minute you’ll find out why that’s not baked into the definition)
• It’s not reserved for people you’re sexually or romantically attracted to—or even people that you could be attracted to

Most of the reason that people worry about whether or not to flirt has to do with the confusion between nonconsensual, sexually-objectifying harassment and healthy, playful, joyful interactions between willing parties. Knowing the difference is incredibly important before we go any further.

Busting the myths

There are a lot of negative ideas about flirting out there that do nothing but hold people back for fear of being creepy, unwelcome, or pathetic. Let’s put those to rest for good:

Hopefully, you’re beginning to see how being a truly great flirt is as different from the old Pepe Le Pew ideas of “seduction” as being a truly great lover is different from lists of bad advice in women’s magazines of the past.

But wait…are you saying flirting is never unwelcome? Or that I’ll never get rejected?

Of course not. People are unique, and their needs, social hot buttons, and desire for interaction can change even over the course of an hour. Sometimes, you’ll make an overture and get shut down hard, or meet with painful indifference. And yeah, sometimes, you’ll realize that something about you isn’t someone’s cup of tea, for reasons that may or may not seem fair.

Every human interaction has a risk of rejection. There’s no guarantee, ever, that you’ll get exactly the reaction you hope for from someone you’re interested in. No one is obligated to give you attention. But just as you manage to hang in there and make friends with people even though you don’t get to be best buds with everyone you think is cool, you can survive having your flirtation attempts shut down.

Social survival tactics: Managing your risk

Let’s talk about a few strategies you can use to improve your chances of your attention being welcomed and your chances of an embarrassing rejection minimized:

• Know your audience. Taking a little time to find out something about the person who’s caught your eye will help you guess whether they might be open to your flirting. If they’re not into your gender, body type, or something else about you, don’t set yourself up for something that’ll be uncomfortable for both of you.
• Cast a wide net. It’s a little bit of a paradox with the strategy above, but if you’re used to offering up a little playful flirtation to lots of people including ones you’re not romantically into, the people around you will start to see that you’re not just hitting on hotties and won’t feel pressured by your attention.
• Pick your moment. Some situations are ripe for winks and repartee, and some are just not. Parties and upbeat social situations, fun selfie threads in groups online, DMs that spun off of a social situation—these are usually safe. Work gatherings, everyday public settings like trains, classes—these are sometimes okay for flirting, but often inappropriate. Err on the side of “don’t”.
• Beware power imbalances. If you are in a position of power over someone, whether you’re their boss or their customer or their mentor, you can never really be sure whether they’re consenting to your flirting or just afraid to say no to you. Stick to flirting with people who aren’t required to be nice to you.
• Don’t go straight for the sexy. You might think your overtly-sexual opener is cheeky and bold, but the person you’re talking to might find it off-putting or threatening. Keeping your banter light and non-sexual at first has a much higher chance of finding welcome.

That brings us to the first actual technique you need for effective flirting…

The opening gambit: Establishing consent

How do you know if someone wants to talk to you, let alone flirt with you? In the social-science field of conversational discourse (told you I was a big nerd!) one way that we check for consent when approaching someone is to use an opening gambit. Understand how this works, and you’re well on your way to becoming a top-tier flirt!

An opening gambit can take many forms, some more direct than others, but all of them contain an unspoken question: “Are you interested in talking to me?” All our systems are engaged to read the other person’s response—not just the words they do or don’t say, but their body language, facial expression, tone of voice, whether they maintain eye contact. When they stay connected, and especially if their response invites you to keep talking, you’ve gotten your first level of consent.

What do you say? Well, that depends on a lot of things, including the setting (a party might invite a bolder opening than a public park), whether you know the person, and your own comfort level. In general, keeping things light and trying something open-ended works. Framing it like a compliment sets it apart from ordinary small talk. A couple examples:

• You look like a person in the know. What’s great to drink here?
• You lit up the dance floor out there! It was almost enough to get me over my two left feet.
• That hair color is just gorgeous on you. It makes me think of that painting Starry Night.

(All gambits, by the way, sound fake and contrived on paper! You need to check out the situation for something to spark conversation.)

A game of calibration

Once someone’s clearly on board to talk to you, how do you steer things into bolder territory when you want them to know you’re attracted to them? This is where flirtation gets really fun and playful.

Remember that game, “Mother May I”? If you were one of the “children”, you had to ask the “parent” for permission for every move you made. The “parent” could re-direct you, telling you to do something else instead. A good flirtation is very similar.

In a famous study, Professor Arthur Aron developed a series of 36 conversational questions that gradually escalated from very casual to very intimate, and had pairs of strangers go through them together. The study found that by the end of the hour they spent talking, the pairs felt as close to their partner as they did to important people in their lives. It was the process of gradually building trust and taking small steps that allowed them to bond so strongly so fast.

When you’re having a flirty conversation, keep these two things in mind: You want to start off more casually, on safer topics or lighter banter, and move into more overtly flirty areas one step at a time. And every time you advance, you want to check and see how your partner responds. One of three things is going to happen:

• They’ll meet you at that level—for example, if you said, “I’ve been wanting to tell you, your eyes are just luminous,” they might smile and say, “It helps that I like what I’m looking at.”
• They’ll see you and raise you, if they’re both really interested and feeling bold. With the previous example, their response might be to lean in a little closer and say, “Well, I’ve been wanting to find out if your lips are as soft as they look.”
• Or, they’ll take a step back to keep you at the level you were at before you tried to step it up. Again with our example, their response might be to sit back a bit, look away, and say, “Thanks, that’s sweet of you to say. So, did you catch the latest episode of…”

If you think of it as a game, as something playful and fun and low-stakes, it can be something delightful that puts some sparkle in your life and a wiggle in your step even if you never talk to that person again. But it also creates a mutually-consensual way to establish what both of you are comfortable with, and find out if there’s real chemistry.

Getting physical

Of course, not every flirtation is a conversation. When you’re across a crowded room or in a noisy space like a nightclub, words might not be an option. And even when they are, your physical signals can turn even the most innocent-sounding conversation into a steamy seduction.

Here’s the caveat: So much of what we think we know about body language, eye contact, and facial expressions comes from neurotypical behavior. And we’re learning every day that “neurotypical” applies to a lot fewer of us than we assumed. It’s harder for some of us to engage in or interpret typically-flirtatious physical signals than others—and that’s okay. We’re always learning.

Here are some tips for ways to show interest through your body, based on what we understand to be flirty, but with some updates for our modern times:

• Eye contact, for those who can maintain it, indicates attention and interest when it’s soft and relaxed, not rigid and unblinking. A smile or “resting pleased face” helps too.
• Indirect eye contact, like looking up from under your lashes or looking at someone out of the corner of your eye, can seem coy or playful or sly.
• Old flirting guidelines used to suggest lightly touching the other person’s hand or arm, or brushing hair out of their face. Nowadays, touching without consent is not cool. It’s still just as flutter-making to say to someone, “I would really love to brush that curl back” or “May I touch your hand?” before you do it.
• We have circles of personal space—our biggest ones for strangers, our closest ones (within a couple feet of our bodies) reserved for intimate interactions with people we trust. Never force your way into a more intimate circle; if you move closer and they back up, honor that distance. But if things are feeling promising, closing the distance between you step by step can confirm that you’re both interested in getting more intimate.
• If you want to be a bit more of a tease, conversely, you can maintain a lot of physical space between you while using eye contact, winks, smiles, and other facial signals to show your interest. It’s also good for inviting them to show interest by coming in closer– and studies suggest that when people come to you, they feel like they like you better and are more interested in you.
• Playing with your hair, letting your hair fall over your eyes, touching your lips lightly with your fingertips, or biting your lip are all classic flirty gestures.
• Quick blinking (“fluttering your lashes”) shows sexual interest. Playful winks and lowering your eyelids a bit are also ways to vary your eye contact.
• Don’t be afraid to be dorky—it’s such a common joke now that finger guns are bisexuals’ primary flirting trick, that doing it on purpose is a way to embrace your awkward but still get your message across.
• Know your style. Do you feel sexier when you square your shoulders, open your chest, and get a little swagger going, or when you lean forward to show off your cleavage, cross your legs, and act kittenish or vixenish? Also, there are no gender limits on how you flirt with your body.

A word about interpreting interest…

Knowing if someone is flirting with you gets easier when you’ve brushed up on techniques like these and start noticing other people doing them. Still, there’s so much anxiety about “what if they’re just being nice? What if I’m misreading the whole thing?” that it’s worth addressing the topic for a moment.

If you think someone is flirting with you, there’s a pretty good chance they are. You’re probably processing a thousand tiny, subconscious things about their behavior.

If you’re perpetually clueless about whether someone is flirting with you and you’re worried about missing out on something good, you can 1) recruit a wingperson who’s better than you at spotting these things and can give you a nudge when they see it, and 2) remind yourself that you’re worthy of people’s flirtatious attention, and consciously ask yourself “could they be flirting with me?” to help yourself remember to look for signals.

If you’re not sure whether someone’s flirting with you, but you hope they are, use the calibration game from above to try to escalate things a small step. If they respond with enthusiasm and a glint in their eye, congratulations, they’re flirting! They’ll calibrate back if they’re not.

Some final tips

Being a great flirt is a journey, not a destination. You can be practicing and building those skills your entire life, so don’t feel like you have to be a matinee idol right out of the gate. Take your time, do what feels comfortable, and celebrate even your little wins—they’ll feel amazing! Here’s a few more things to get you started on the path to devastating charm:

• Authenticity is key. People are pretty good at spotting an insincere player, and it’s a turn-off. On the other hand, being real and radiating you-ness makes people feel great.
• Likewise, don’t play it too cool. The joy of someone flirting with you is their enthusiasm for you, their fascination with you. Don’t act like you’re deigning to pay attention to someone—let your interaction with them be a high point of your day. They’ll feel it.
• Think flirty thoughts. Your inner state will show on your face and color your voice, so let yourself think about being attracted to this person, or how you’d like to kiss them. If that seems like it would fluster you, just think, “This person is amazing and I feel amazing talking to them!” They’ll get that vibe from you even though your thoughts are unspoken.
• Never “neg”. I have rants for other days about my dislike for pick-up artists, but one thing I especially hate is “negging”, or trying to get someone interested by subtly putting them down. Why did anyone ever think this works? Playing on people’s insecurities is gross, not sexy.
• Make them the center of your world for five minutes. Really focus on the person you’re flirting with. Don’t check your phone, don’t let your gaze wander around the room. Get absorbed in them like they’re the only person who exists for you right now.
• Take space to reconnect. Don’t be afraid to put a good flirt on pause for a little while—excuse yourself to go to the bathroom, refresh your drink (and theirs?), greet a friend. As long as it doesn’t seem like you’re trying to escape, it leaves them eager for more and gives you the chance to create fresh sparks when you smile at them across the room or seek them out again.
• Be careful what you compliment. In general, anything about them that they control, like their sense of style or taste in music, is safe to compliment. Body parts or looks are riskier; if you want to go that route, be creative. “You have really beautiful hands, like a piano player’s” is both safer and more original than “you have a great ass”. “You’re just radiant when you smile, I want to bask in it like a cat in a sunbeam” is more memorable than “God, you’re just so beautiful”.
• Use obvious jokes and exaggerations. This is definitely a place where you want to embrace your inner dork and not take yourself too seriously. To do this, you have to be willing to go over the top in service of making them feel good—for example, “If you look at me like that again, I think I might get the vapors and swoon!” (and then mock-swooning when they call your bluff.) It’s silly and charming and most people will feel thrilled and delighted by it.
• Keep it about them. Even if you’re eager to hook up with this person, don’t think about getting a quid pro quo for your excellent banter. Spend your time focused on how fascinating they are, on making them feel fabulous, on encouraging them to talk about themselves. Ideally, they’ll do the same for you without you having to center yourself.
• If you both had fun, you win! That’s the only outcome that really matters here—that you both felt alive, engaged, sparkly, playful.

Oh—and one final tip: Don’t forget to flirt with them once they’re your long-term lover! Nothing is sexier in a relationship than feeling like your beloved wants to win your heart again and again.

What were your most memorable flirting encounters? Did you have a moment when you were silky-smooth, or adorkably endearing? Drop them in the comments—we’d love to hear your stories!