This Is Why Your Flirting Is Falling Flat

Dating apps and texting leave a lot to be desired in terms of building a solid rapport with any potential dating interest. We can’t read body language or observe a person’s attraction and receptiveness over text or DM. And unless you’re some elite-level smooth talker, it can be a bit daunting and challenging to flirt over text and be well-received.

By Jenny White5 min read
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Many people today lack basic etiquette and social skills due to being glued to their phones 24/7 and being distracted. They say the average human attention span today is a paltry eight seconds. You have eight whole seconds to make the conversation interesting and capture someone’s attention. Can you make your flirting effective and sustain someone’s interest in eight seconds? Yes, you most certainly can.

As a dating coach, I constantly run into a brick wall of incessant social awkwardness and lack of social decorum in many of my clients who feel crestfallen when people don’t text back within two minutes. People have trouble communicating and being sociable to any degree that would leave an onlooker intrigued and hungry to know more and build sustainable attraction. 

Additionally, many people on the dating scene may possibly feel outcasted and detached from others: According to the Health Resources and Services Administration, "1 in 5 Americans say they feel lonely or socially isolated. Loneliness can result in an urge to seek attention, even in people who don’t normally exhibit attention-seeking behavior.”

It’s no wonder people can’t seem to weather the unknown variables and ride out the unpredictable course in terms of meeting someone new. In their quest for attention and validation, they feel they’re entitled and demand an immediate text back, a.k.a instant gratification, for their efforts. And if they don’t receive it, they throw a fit, they inevitably say something they regret, and they wind up ghosted and blocked. 

For the ghoster/blocker, this is extremely awkward and unattractive. No one likes to be put on the spot and be made to feel uncomfortable by someone they barely know. And let’s face it, it’s woefully uncomfortable to come in contact with a person who demands our full and undivided attention when you've barely exchanged a few simple words. It screams insecurity, social awkwardness, and “weirdness.”

The Basics Behind Flirting

You must take into account how the other person feels (and wants to feel) during those first initial exchanges. When people engage in a conversation with a new person they’re not well-acquainted with, they want to feel relaxed and unforced, and they want it to be fun. They want the conversation to flow naturally and to sense a vibe with the person that will allow them to connect and be attracted.

Thus, when you flirt with someone, try to put yourself in their shoes. How would you prefer someone to address you and speak to you? You’d want them to be cool. You’d want them to be fun. You’d want them to be able to carry on a conversation that just flows seamlessly in a positive direction.

Make people feel good, and they’ll desire to be around you and will enjoy your company.

Concentrate on having fun. Nobody wants to hear you complain about your job, your ex, your crappy boss who’s constantly riding your butt, or your body image issues and insecurities. Those are perhaps for another time when you’re in a committed relationship and have the liberty to share your problems and come up with solutions.

Instead, talk about your basic stuff people want to hear about and relate to in a romantic sense: 

“I like the way you talk and the sound of your voice.”

“I like that joke. You’re very clever, aren’t you?”

“I like you in this picture. Looks like you had a great time.”

Make people feel good, and they’ll desire to be around you and will enjoy your company. Simple enough.

Active Listening Skills Help Immensely with Flirting

You must learn to pay close attention to intricate social cues in the way people respond to you. If they’re backing off, you back off. If they’re moving in closer and being more engaged, you move in closer and be more engaged.

Think of it like a dance where two people are searching for that perfect conversational rhythm that flows naturally. Listen intently to what they say and take a moment to think of how you’ll respond. 

Above all, relax. They’re behind a text window/DM screen. There is zero pressure for either of you to respond in a timely manner, especially in haste where you may risk saying something embarrassing and you turn off the other person.

Instead, take a moment to listen to what the person is telling you where you can follow up with a proper and fitting response.

I give my clients what I call the “listen, repeat, and affirm” angle in conversation: you listen to what a person says, you repeat it back to them, and you affirm that you’ve understood by responding with something relevant and empathetic in context.

When a person feels heard, understood, and empathized with, then a connection can be built.

For example, your potential love interest says to you, “I visited XYZ band at a debut concert several years ago, and I had a blast.” You can proceed to follow up with, “Wow, XYZ band? That must have been a really great show indeed. Now I definitely have to see them soon too.”

This demonstrates proper conversational dynamics where the person feels heard, understood, and empathized with – which is the basis behind any fruitful and promising connection between two people. If you have trouble with banter and being slick and flawless with your words, the listen, repeat, and affirm method can be a handy tool in your repertoire to establish a meaningful connection.

People want connection. And the best way to connect with others is through relevant experiences that they can share with another person who listens, understands, and “feels” with them in sharing personal details about their lives. You don’t have to be overly skilled in your wit and vocabulary to accomplish establishing a connection with someone in a meaningful way.

A Few Sincere Compliments Go a Long Way

“You’re hot” is the most basic and banal go-to compliment in addressing someone you’re flirting with. And when it comes to women especially, it can fall on deaf ears if she’s accustomed to hearing it from multitudes of men she remains uninterested in because “hot” just sounds lazy and thoughtless.

Instead, for guys specifically, find something exclusive to the woman that makes her stand out to you and others. “I like your bracelet. It’s unusual. I’ve never seen a bracelet like that before.”

“You’re hot” just sounds lazy and thoughtless.

For women, men rarely receive compliments, and it curls their toes to receive compliments from a woman. Want to really make a large, impressionable dent in man’s mind for eternity? Compliment him. Tell him he excels at something that’s unique to him. Tell him you like the way his shirt drapes over his broad shoulders. Mention to him you like his shoes, and he’s a sharp dresser. 

However, don’t overdo the compliments because then it just sounds insincere. A few meaningful and detail-oriented compliments that zero in on personal traits and characteristics go a very long way.

How To Text Flirtatiously without Turning People Off

Now comes the really important stuff. As we mentioned earlier, it’s important to allow the conversation to flow naturally, and forcing a text that sounds awkward while demanding attention and validation from people within 3.2 seconds is not a sound strategy to get people interested and stay interested. 

Rather, give people an ample amount of time to answer you while you also allow yourself a window of time to come up with something intriguing to say. Don’t text them too much! In the initial stages when you don’t know each other, it’s best to allow a bit of time in between texts and to “leave them hanging,” so to speak, as it helps build an air of mystery. 

For example, you say something like, “I thought about how we met the other day, and it made me laugh.” 

In the initial stages, it’s best to allow a bit of time in between texts and to “leave them hanging.”

This naturally provokes curiosity in the recipient, and they will lean towards asking probing questions like “Really? What made you laugh?” Now, let them wait for a response. Meanwhile, they’re thinking about you and the interaction, and they will be anxious to hear the answer. 

How long should you let them wait? An hour or two.

“What?! An hour?! They’re going to lose interest if I don’t respond right away!” is what many people generally think. And they couldn’t be more wrong.

Instead, it conveys that you’re leading an exciting life and you’re not waiting around to thirstily answer texts. Do this over the first few days of interacting with someone and as the conversation begins to pick up, you can find more time to engage with them. As their level of interest increases, you can allow your interest level to increase in tandem.

The main thing is, you ease your way into the conversation by not pressuring, not making the other person feel awkward and uncomfortable, and you’re allowing the interaction to build into something more promising where people actually enjoy flirting with you and talking to you.

Closing Thoughts

Flirting is a lost art, and it’s become a bit of a chore to many who feel like their efforts aren’t welcomed with open arms because they often trip themselves up in not allowing the conversation to flow naturally.

Think of your flirting partner in terms of how you’d think of yourself. What would pique your interest? What would make you want to engage in titillating conversation? What could the other person say to you that would draw you in effortlessly?

Concentrate on the social-conscientiousness aspect of flirting and how you want people to respond to you by putting yourself in their shoes. It’s a pretty safe bet you wouldn’t want to be awkwardly pushed around and backed into a corner by a stranger either.

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