If Your Text Conversations Never Lead To A Date, Here's Why

It's time to murder your darlings, awkward people.

Pexels | Photo by Mary Cherkesova

*This article first appeared in Heart Affairs on Dec 30, 2022

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I match with Simon* on Hinge, and I know exactly how the conversation will end before it starts. I know because his profile reads like every egocentric person who lost their curiosity about others the moment they looked in the mirror.

He chooses the dating prompt: "The way to win me over is…"

He responds, "By showing a genuine interest in me."

I see this often on dating profiles. It's all "me" and not a shred of "we." These people are looking for validation, not connection.

But I have been pleasantly surprised/wrong about people before, and Simon is hot, so I play ball…

I compliment one of his vacation photos. I then ask him where the picture was taken and what he remembers most about the moment. Standard small talk stuff with the opportunity to go deeper…if he chooses.

Simon answers my question like he is describing an infectious rash. But his unflowery response is not the problem. The problem is that he doesn’t ask a question back.

So I build on his response and ask another question.

He answers. The rash grows.

The conversation builds more. I ask more questions. He asks nothing back.

Now, I am getting the itch to leave this one-sided conversation…

My questions thus far have been tame, so I ramp up the volume and ask quirkier questions. His answers get more colorful, but again…he asks nothing back. Damn, this conversation has now erupted into plague buboes. (Did I say I would stop using disease metaphors in my articles? You know I lied.)

I stop texting him and go eat a salami sandwich. (Don't judge. One must eat processed foods after being spit out of the dating app food processor.)

Now, I know what you are thinking. This guy is just being polite. He clearly is not interested. You ask questions when you are interested in someone. Duh.

Oh, but wait…he is.

The next day, he texted the usual "hey" horseshit. I didn't respond. Mostly because I would rather gouge out my eyeballs with a pick axe than interview another dullard on a dating app. (And I have run out of salami.)

The next day, he texts again. But not to get to know me. Oh no. To tell me more about himself. With a smarmy salesman pitch, he boasts about his job.

Again, he asks nothing back.

I once tried to teach my cat how to play fetch. This conversation will end the same.

Unfortunately, the conversation with Simon is not an anomaly. I have had hundreds of similar text exchanges with men on dating apps. I usually unmatch after 3–4 questions without any questions back. I strongly recommend you do the same.

To be fair, this is not a gender problem. My male friends tell me they encounter the same poor conversational skills on the distaff side.

But if you are a Simon…cut that shit out. A dating app is not an advertisement for how awesome you are. It is a place to connect with equally awesome people you would like to date.

Here are a few tips to make those connections deeper.

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Ask a question that will lead to a story.

Have you ever noticed that when a speaker begins with a story, you are far more engaged with their presentation?

When we hear a story, we feel what the protagonist feels. For example, you can tell someone that your vacation spot was balmy. Or you could show how hot it was through a titillating tale of a handsome pool boy hosing you down whom you later went for drinks and…

You get the point. Stories ignite the senses.

But often, we ask questions that would not inspire a story. For example, instead of asking, "Where did you grow up?" you could ask, "What is your craziest memory from your childhood?" Or you could ask something specific, such as, "Who was your best friend from childhood, and why?" It's the why part that leads to a story.

Stories bond us to others. Or as Jonathan Gottschall explains in The Storytelling Animal: How Stories Make Us Human, "by encouraging us to behave well, story reduces social friction while uniting people around common values. Story homogenizes us; it makes us one."

In contrast, general questions will garner general answers. So if you really want to get to know someone on a deeper level, ask a question that will make them recall an experience and inspire a story.

Find your “Et Tu, Brute?”

If you want to pierce someone in the solar plexus, you must find commonalities. We are attracted to the familiar. Some commonalities that build rapport:

• You may be familiar with a landmark, restaurant, or someone from their area. Location often builds familiarity.

• Similar hobbies and pastimes always build rapport. Nothing makes a conversation hotter than sharing a passion.

• People put their Spotify lists in their profiles for a reason. One study found that music was the most common conversation builder with strangers. Another study found that those who liked the same music had stronger compatibility.

• You can also find the familiar in the future. The icebreaker question of where you would like to go on vacation next works for a reason. It gets you dreaming about hot, steamy sex in an exotic location.

Nix the "Hey Beautiful" conversation starters

If I had one lousy ducat for every time a man started a text exchange with "hey beautiful," I could fund my "need perkier tits to deal with this crap" GoFundMe campaign.

Try this instead — give a genuine and specific compliment.

To be clear, it's ok to use that opener with someone you have already been on a few dates with, but if it is a total stranger…how do you know she is beautiful?

Have you woken up beside her, without makeup and a good night's rest, and thought, "God, you are beautiful," Have you seen her hula hoop with a top-shelf bourbon in one hand and a glow stick in the other? (This is not a personal reference…maybe.)

Someone becomes beautiful when they become unique. You don't know what makes this person unique, so stop bending the plot curve.

Go easy on introverts.

It's often hard to gauge who is introverted vs. extroverted on a dating app, but the photos offer clues.

For example, extroverts tend to post more group pictures or connect their social media to their apps.

Activities are another giveaway. Extroverts will seek out adrenaline-raising activities. So if someone is bungee jumping out of a plane, they are more extroverted than someone who posts photos of quiet, contemplative moments.

This is important for a reason. You have to start slower with introverts and ask non-threatening questions.

One tip is to ask number-based questions because they are more straightforward. You could try "How long have you lived here?" or "How long have you been working in that field?" (DON'T ask how long someone has been on a dating app or how long they have been single on your first conversation. Gross.)

You have to engage in some small talk.

I really hate small talk. I don't want to wade in the kitty pool. I want to plumb the depths of the Mariana Trench…right away.

But if you are one of those deeper souls, you must engage in some small talk. You can sprinkle in the saltier questions after you let the meat heat up. The trick is timing and patience.

And if you are one of those slow-burn types who gets unnerved by people who skip the small talk, here's a word of advice. Sometimes the people who say awkward, inappropriate things are the ones who will most tie your heart in knots.

Small talk is a skill. It is not a character trait. You can only know whether someone has an honorable character after genuinely knowing them. So next time someone says something dorky or strange (as long as it is not sexual), take a beat and realize that they are probably nervous and not their usual comfortable selves.

If you are not feeling it… it's ok to ditch the conversation.

Some people suck at conversation. When you ask these folks how their vacation was, they will tell you it was "nice" instead of launching into a tragic tale about how they lost their passport while playing pachinko with two Japanese movie stars. (That might be a personal reference.)

Of course, with some shy people, "still waters run deep." It takes time to get to know those people. And with others… "still waters" are the perfect breeding ground for flesh-eating bacteria. (Damn…more disease metaphors. I am incorrigible.)

Unfortunately, not everyone who gives cryptic responses has an undiscovered crypt inside their mind. Sometimes, dull answers are a sign of a dull mind.

Personally, I used to worry that my weirdness scared off men. But over time, I realized it only scared off the ones who were not right for me.

So if the conversation is not vibing, trust your instinct and leave it.

I never have these problems when I meet men in person. I used to think it was because I was more reserved (read: behaved) in public, but now I have a different theory.

When we are on a dating app, we fall into transaction mode. Does this person check the right boxes — age, height, income, location, intent (i.e., casual or relationship)?

When you meet someone in person, the purpose of the conversation is to make conversation without ulterior motives. You don't know if the person is taken. Nor have you "matched" with them, so you don't even know if they are attracted to you. You are starting at ground zero — mystery.

A great conversation is like an engaging novel. You can't wait to turn the page. But just like any novel, one person might love chic-lit soft porn while the other might prefer a dystopian about a mutated outbreak of syphilis.

(I would say that is my last disease reference, but…)

Carlyn Beccia is an award-winning author and illustrator of 13 books. If you enjoyed this article, please share this publication with friends. Wednesday’s content is always free. Sunday’s content is available only for paid subscribers.