The Art of Flirting

The Art of Flirting came together as a workshop in the spring of 2024. I "promoted" it by talking to people: I'm doing a flirting workshop, would you come? People reacted immediately: one person backed away from me. Quickly. Another sneered at my use of the word "art" and said: I'm tactical. But most people were both discomfited and curious. I heard a lot of: I'm bad at flirting. I don't know how to flirt. I can't tell when people are flirting with me.

As a professional with sex in my title I'm accustomed to discussing topics and instigating conversations most people avoid. I'm comfortable with it and into it and that is part of what makes me good at my job—my comfort transmits and is necessary for working well in such vulnerable territory.

There was a time though that I lost touch with the ease I take for granted now. I'd gotten so far from myself that I'd forgotten how to flirt. Shame about sex, and pleasure, and fun had taken over my insides without me even noticing. When I came to and realized this had happened, one of the ways I found my way back was to flirt, with intention.

What I did was: start to notice people again. To really look. Make eye contact. Banter a bit. With the barista, the checkout clerk, the people I interacted with on a daily basis. I was out of practice and I felt it, but I kept going. I escalated. To giving compliments. Nothing big, nothing real effortful. Things like: you have a great laugh. I really like that tattoo. Saying that now it sounds simple but at the time it was excruciating. So I investigated and asked myself what the hell was going on that made this seemingly simple exchange feel so incredibly hard.

This is what came up:

What if I embarrass myself? What if I embarrass them? Will I make a fool of myself and feel humiliated? Is it too vulnerable? Will it be taken wrong?

But the more I did it, the more comfortable I got and what I noticed is that sometimes I was embarrassed, and sometimes they were embarrassed. And nearly to the one, it made everyone's day. 

Like the time I complimented a bakery owner on her amazing eyes and she looked coyly over her shoulder at me, sparkled and said: Oh, I like you too! I walked out of that shop feeling taller and lighter than I'd walked in. 

Or the time I told the young woman at the grocery checkout that her facial structure was incredible. She got so flustered it made me blush (I still worry about being too much, or having a negative impact). I said: oh I'm so sorry I just, I'm trying to practice saying the nice things I think out loud. It's a whole thing I'm doing. And she said, still barely able to look in my direction: No, no, I didn't even put makeup on today and I really needed to hear that. I left, relieved to move on from the vulnerability of the moment but also knowing that that brief interaction was meaningful, and positive.

Flirting isn't what people think it is. We're only bad at it when we think of it as a means to an end and the end doesn't come. The measure of successful flirting isn't getting the number, getting laid, getting the ring—it's whether you've enjoyed yourself.

Level 1: Make Someone's Day

Social

This is where it all starts—with the generous and genuine compliment. The day you make might just be your own.

The generous part is key: no agenda, nothing expected in return. That said, this practice has opened up possibilities that would've never occurred had I kept my mouth shut. 

First, notice. Really notice people. And what strikes you or makes an impact—visually, emotionally. You can do this anytime anywhere. 

• Center yourself. 
• Take a breath. 
• Drop your shoulders. 
• And just look. 

What to notice. Anything that really stands out. Something they're wearing or how they're wearing it. A color that really pops. Something specific about their looks—the bakery owner had the kind of skin porcelain refers to. Red lipstick. Green eyes. I was literally struck by this combination even though all I said was you have amazing eyes.

You might notice something about the interaction itself, or how you feel in a person's presence. I've known people whose laugh makes me feel like the funniest and only person in the room. I have a friend who, when he listens, you know he's really listening and what you say matters. This kind of noticing counts too, and it's often what generates the most impactful compliments because it names something the other person can't see in the mirror.

Take your time. You don't have to say anything at first. Practice looking. Relaxed stance, no pressure, lots of room to breathe. Noticing, and presence, are real skills. Take a few days here—or weeks, if you like. Every level of flirting builds from here. 

Then say it. Risk accompanies engagement—discomfort, embarrassment, intention not matching impact. This is also where the skill develops, where the muscle builds. If the compliment lands, notice how it feels all around. If it doesn't, let it be. Don't push.

Don't follow a script. Follow your attention.

Level 2: See What's Possible

Suggestive

This is what most of us think flirting is: showing subtle (or not so subtle) interest, getting a number, asking for a date. Where level 1 is social skill—a low stakes practice with a lot of potential to be uplifting, connecting, and playful—level 2 has more intention behind it. Suggestive suggests attraction, and desire. 

With attraction and desire come vulnerability and uncertainty. It's no wonder that this level gets flooded with strategy and tactics. But staying true to the art of flirting, we start from the same ground as level 1—genuine and generous—and escalate with an invitation, never a manipulation.

Authenticity is vulnerable, vulnerability is exposing and nervousness comes with the territory. Even as our confidence grows, it doesn't cancel out the feelings, nor is that the point. Anxiety and excitement sit right next to each other in our nervous systems.

Two things to know before escalation. First, level 2 builds on level 1 and assumes—ideally requires—that initial engagement goes well. The presence and the confidence we're building in the lower stakes practice translate here. Second, this is experimental and open to possibility. Relationships and sex are best approached as creative endeavors. Flirting is a great entry point to this orientation.

Be brave.
Take a risk.
Say the thing.
Be open to hearing "no."
Be open to hearing "yes."

Practice: The Ask

This practice is excellent for level 2 flirting and life with others generally. It builds resilience for asking, for answering authentically, and being with whatever response we get. Practice with a friend, a partner, or anyone you trust and feel comfortable with. 

It goes like this:

Think about something you'd like from the other person. Make it a genuine but low-stakes ask—an in-the-moment favor, a coffee, a small piece of information.

Person A starts with a request. Some examples if you need them: 

• Will you sit next to me? 
• Would you like to get coffee with me?
• Can I get your phone number? 
• Will you make dinner tonight? (not explicitly flirty, but who knows what might happen!)

Try not to soften a "will you" or "I want to" by burying it in a "would you like to" or "would it be okay with you." Would I like to make dinner tonight? Not especially. Will I? Yes. This practice is about expressing a want, a desire, clearly and confidently. And being able to trust yes because no is accessible.

Person A makes the request.
Person B answers: Yes
Both people take a moment to reflect privately on how yes landed.

Person A makes the same request again.
Person B answers: No
Both people take a moment to reflect privately on how no landed.

Person A makes the same request for the third and final time.
Person B answers authentically—this time the response isn't scripted.
Both people reflect, with Person B paying attention to how they know the authentic answer is authentic. What somatic signals accompany the aligned response?

Switch Person A and Person B and run it again.
Debrief by sharing reflections with each other.

Taking a no gracefully, in the moment or if things change, is a grown-up skill that we all could get better at. So is really taking in a trustworthy yes. Especially as the current heats up and expands into level 3...

Level 3: Make Something Happen

Seductive

The skills developed in the first two levels can be engaged in many contexts but feed something different here. Level 3 isn't platonic, it isn't everyday exchanges—it's sexual, romantic, and partnered (whether for a night or a decade). Seduction is a skill that requires fluency—in emotion, eroticism, boundaries, and communication. The same invitation-not-manipulation thread runs through all of this, with the temperature running hotter and the stakes higher. Unattached, generous arousal in this context is what makes us feel invited in rather than worked over.

We think of, and think we want, arousal to be spontaneously exciting. It's easy to get swept away by hormones, new relationship energy, the anxiety-excitement of will they/won't they. But when that wanes, or isn't present, we're left without a roadmap. This is when a lot of couples show up in my office, carrying the question: how do we get the spark back? A question sometimes coded as mismatched libido (a deeply misunderstood phenomenon that's a longer conversation than this essay can hold—and one I have often).

Flirting isn't the whole answer but it's definitely part of it. When we treat the flirt as pre-game—a tactic designed to achieve an outcome—it gets retired once that outcome is achieved. To our detriment. Flirting is a fundamentally erotic practice—playful, creative, open to possibility. It keeps the pilot light lit. Fluency at this level means we can turn the heat up, or down, with intention.

Level 3 is the most personal, the most responsive, and the least scriptable "flirting" in this whole progression. There are some things we can't learn except in the doing of them. Imagine trying to learn the piano, or the tango, by only reading about them. Instruction, guidance, and the kind of generative discomfort that facilitates real growth are needed, even when natural talent is present. Specifically in this realm of sexuality and relating, trying new things on our own tends to stay self-referential—we move inside parameters already familiar to us. This is where working with someone who's traversed the territory comes in.

A preview of what the work looks like:

This is a consensual practice with a partner. Take the noticing from level 1 and ramp it up. Look at your partner. Notice what about them turns you on. Pick a body part and look. Let lust infuse your attention. Not love. Lust. If that's hard or impossible to access, fake it. Let it be goofy, playful. And let your partner see you seeing them.

Switch.

Debrief: What was that like for each of you? Did anything surprise you? Make you curious, or want to take it further?

Don't stop flirting

Practiced as an art in itself, flirting is the current that enlivens and runs through everything—a moment, a friendship, a partnership over time. 

It's not a strategy for getting the thing you want. It is the thing you want. The measure of success isn't in a future outcome, but in our enjoyment in the present. So why would we ever stop?

More of this
This essay is a free preview of a paid tier in development.
A flirting guide is coming: the levels, archetypes, dos and don'ts, and more, for handy reference.

The Art of Flirting workshop is still a thing—reach out directly to bring it to your org, group, or community gathering.
For more on working together, visit The Pleasure Ethic.