The Work To Find Someone Enchanting — Flirting Basics 101

The movie Hitch comes up quite a bit when my generation thinks of people that get into dating advice and coaching. If you aren’t familiar with this 2005 Will Smith and Kevin James rom-com: a successful, private dating coach cleverly named Hitch who specializes in flirtation techniques helps a nerdy financial consultant land the woman of his dreams, but also learns that the nerd’s authentic self was the key factor in obtaining his dream girl all along. It’s cute, funny, dumb and stereotypical in an easily digested way, with fun subplots and… whatever. Not perfect by any means, but in general, a good time (I’m a sucker for physical humor). I’ll admit, I think of it often, because it does focus on analyzing bad dating habits, and toys with the idea of modifying behaviors for the sake of attraction — a subject I’m most interested in.

In the opening scene of the film, Hitch says to a nervous client that wants to impress his date, “Listen to what she is saying and respond. Listen… and respond.” I love this simple piece of advice and if we had a room full of daters, many heads would be nodding in agreement as they flash back to either getting their ear talked off by a date who doesn’t take a breath to ask any questions back, or the opposite — the dreaded awkward silence date. But I think “listen and respond” is missing some very important context as to why we should ask questions and what it says about us as people.

Asking meaningful questions about a person comes from a place of authentic curiosity and that is a key factor in flirtation. Firstly, it shows confidence and smarts. Secondly, do you give a crap about who the person in front of you really is or not? Are you checking off boxes or is your brain turning over their words and sparking fresh topics that make sense? In fact, faking that curiosity and asking questions because someone told you to and not because you’re genuinely curious, would be a recipe for disappointment. That’s not connecting; it’s acting.

Learning about each other through some genuine Q&A prompting is what sets the stage for finding common ground and building rapport. Rapport, oof. It’s such a distinguished sounding word, but look at its definition according to Oxford Dictionary — “A close and harmonious relationship in which the people or groups concerned understand each other’s feelings or ideas and communicate well.” Bingo! That’s what we want.

Concern for understanding each other’s feelings! Communicating well! Hell yeah, the first few dates should be all about finding that “close and harmonious” place if it exists between you. And that takes some digging at first — digging that is personal to you as the question asker! What do you actually care about and how can you lead the conversation there to find the fun?

If you’re not asking at least some curious questions and expect the date to be filled by talking about yourself to no end, or waiting to see how well the other person “performs” and entertains you, you’re there to feed your ego. Go ahead and stop that. Get fascinated by people without an obligation to be in love with them. Be a generous listener and don’t hijack the date with your inflated (or perhaps nervous) ego. Your date has a world of cool in them — find it! Even if at the end of the date, you both aren’t right for each other romantically, there is incredible value in discovering what’s interesting and enchanting about a person. That’s it. That’s your job on a date — discover who each other are. And when you can get to a place where learning about someone is fun no matter the outcome, the conversation flow will be easy as canned pumpkin pie (whip optional).

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What about once you’ve already gone on a few dates? Is the conversation… waning? I’ve had a few times where I’ve been stumped when a guy continues to ask very basic things and doesn’t build off the knowledge that was established previously. If they don’t have any concern for that problem at work I mentioned, or wonder about which plant I decided on for the kitchen, or ask if I have leftovers from that awesome dinner I sent a photo of from the other night, I wonder…. do you listen? What purpose is this serving?

Asking questions is not just about performing the duty of look, I cared today, I’m done — it’s about actually giving a shit. If you aren’t motivated to ask good questions, you’re probably not into it. Move on. Good dates light your fire with questions. Falling head over heels for someone is about loving how they relate to the world and people in it. It’s about habits in their personality, their humor, their emotional feedback. If you don’t care about those things, you might be assessing superficial characteristics that don’t lay the groundwork for true connection. In a funny way, being curious is the ultimate flirt game to acquire. It’s what makes other people feel truly special.

“Hey, what if I’m asking questions and my date just doesn’t say much?” you might be pondering. Yes, let’s get into pitfalls, like the one word answers. Guys and gals, you’re killing us with these. If your date is asking you questions and your response is less than four seconds every time, why the heck are you there then?! You must be generous with your answers and be willing to tell some stories and give some opinions in order to keep the conversation moving, and then think about how it connects to the other person. They’re asking for a reason, they want to know! And they’re probably hoping you throw some curiosity back the other way. It takes two. Don’t be a downer. Mystery has its limitations. When I’m on a date where the other person is being too cool for conversation, I wrap it up. The comfortable silence phase doesn’t come until later.

Let’s say you’re someone like me and you might be a little self conscious about talking too much because once you get goin’…. (I hate it when I do that.) So, I (try to) let my dates steer the conversation and I like to see if they have any curiosity about something first. I’m not feeding them information they don’t care about yet, I’m answering honest questions and then digging into the subject a little more and comparing notes. If it’s a subject I find offensive or don’t care much about, I’ll take initiative to steer the conversation another way. And hey, if you can’t stand sitting in front of this other person for one moment longer, get up and leave with a polite goodbye. I’ve never had to do that, but I’ve had a few times where I was glad the date was over when the effort to find the enchantment was just a little too hard.

A parting thought — be careful of falling prey to always giving negative responses and approaching all questions and answers under the assumption that your date is trying to dissect you and find fault. Hopefully, you’re both there to have fun and learn, not search for incompatibility with scrutinous eyes. One quality I stay away from these days is the inability to show someone you find them charming. You gotta give in just a little bit and indulge the questioner. The constant rebuttal where conversation is always on the defense will become weary after so long. I’ve had one too many experiences where every question I ask is reframed as if in disagreement. “Do you love dogs?” I might ask. “I don’t love dogs, per se, I mean dogs are great and I like mine, but not everyone’s dog is great, like I had an ex once…” You get the picture. I’m trying to find something fun to talk about and dogs seemed safe, but no. Even the dog topic crashed and burned. Now, imagine every question being reframed on the defensive. Rough time for a date. Not easy and fun. Just exhausting.

Bottom line: be kind to your date and remember to exchange curious hearts and minds, no matter the outcome. Maybe you’re a private person and don’t like to talk about yourself or a subject has been broached that makes you prickle — take charge and go another direction. Stay positive, stay thoughtful and show interest in their life details, not just as a kind service to them, but because it serves both of you. Alright, ready for some date jeopardy of your own? Get Out There and Date for 200, please.

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This post was previously published on Hello, Love.

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