By Danielle Andrews
Kelleher International was founded long before the digital age, but as communication styles have evolved with less in person first meetings, we’ve grasped the importance of making sure digital interactions are on point and meaningful. Our clients have been a bit flummoxed at times about how to approach this somewhat evasive, slippery form of communicating. How do you make a good first impression via text? How do you not come across too over zealous or too aloof? Understanding that too much texting back and forth before a first date might be a hinderance. So, as the need arose we began to incorporate this new communicative art form into our client coaching. The following is a compilation of the advice we give our clientele.
The Importance of Being Understood
Have you ever been texting and just couldn’t figure out how to express what you were actually feeling? You know the person on the other end is watching those little dots blink … and blink … You try several different ways to say something, second guessing yourself until you just stop and either send nothing or something short or even terse? Have you ever hit send only to see, after the fact, that auto-correct beat you to it and sent something totally inappropriate, embarrassing or rude?
There’s a cruel irony at the heart of modern dating: we have more ways to communicate than ever before, yet we’ve never been more misunderstood. A three-word text sent at the wrong moment or with the wrong punctuation can unravel days of good chemistry. A perfectly crafted message can make someone’s heart do a small, embarrassing flip before they even put their phone down. The difference between those two outcomes? Intention, timing, and the quiet art of wordsmithing.
Texting in a dating context isn’t just communication — it’s performance, interpretation, and a surprisingly delicate dance. Here’s how to stop being misread and start saying exactly what you mean.
The Punctuation Problem Nobody Talks About Enough
Before we get into strategy, let’s address the elephant in the chat thread: punctuation carries enormous emotional weight now, and most people don’t realize it.
A period at the end of a casual text doesn’t signal grammatical correctness anymore — it signals coldness. “Can’t wait to see you.” reads measurably more distant than “Can’t wait to see you!” or even just “Can’t wait to see you” with no punctuation at all. The absence of a period has become, in texting culture, a warmth signal. This isn’t a rule anyone voted on; it’s just where we landed collectively, and ignoring it means your messages might be landing differently than you intend.
Similarly, “Fine.” is not fine. It never was, but in text form, it’s a small grenade. “Fine!” is enthusiastic. “Fine” (no punctuation) is neutral and breezy. Context is everything.
The Do’s:
Do use mirroring to build rapport. Match the energy and length of the other person’s messages, at least loosely. If they’re writing three sentences with a little humor, don’t respond with a one-word answer and don’t write them an essay either. Mirroring signals that you’re present and engaged, not performing or distracted.
Do name the tone when it’s ambiguous. If you’re being sarcastic, say so — or use a tell. “You’re obviously the most punctual person I’ve ever met, lol” lands very differently than “You’re obviously the most punctual person I’ve ever met.” That italicized “obviously” does real work. So does a well-placed “haha” or “lol” — not as filler, but as a genuine tone marker that signals you’re being playful, not pointed.
Do use specific language to show you were listening. Instead of “that sounds fun,” try “okay but a midnight taco run followed by bad horror movies is genuinely my ideal Saturday.” Specificity reads as warmth and interest. It shows you absorbed what they said and responded to them, not just to the concept of conversation.
Do let excitement be visible. People are so afraid of seeming too eager that they sap all the energy out of their messages. Enthusiasm is attractive. If you’re excited about plans, say so without apologizing for it. “I’m actually really looking forward to this” is not too much. It’s just honest.
Do re-read before you send. Spend three seconds reading your message as if you received it from a stranger. Would it land the way you intend? It takes almost no time and saves enormous amounts of confusion. If you’re in a hurry sending a text; texting while driving or walking into a meeting, chances are you will be curt or make an unintended typo. So sit down and take your time.
Do resolve big conflicts in person: This could have gone into the Don’t column as in “Don’t handle big conflicts via text.” Geraldine K. Piorkowski Ph.D. writes in Psychology Today, “Discerning when another person is angry, pleased, or disengaged depends heavily on observing eye contact, tone of voice, vocal inflections, facial expressions, gestures, and motor behavior, which cannot be gauged readily via digital means.”
There are some arguments and issues that really require in person attention, where body language and tonal inflection are necessary to avoid critical misunderstandings. So if someone is attempting to resolve an emotional conflict via text, respond with something like; “I hear you, but I feel we need to discuss this in person, when can are you free?” 🙂
The Don’ts: The Habits That Quietly Torpedo Things
Don’t use “k” unless you want someone to wonder what they did wrong. It is, without question, the most loaded single letter in the English language when sent in a romantic context. Even “okay” reads more neutrally. “Sounds good!” reads warmly. “k” reads like you’re tolerating them. If that’s not what you mean, don’t send it.
Don’t go quiet without a heads-up. If you’ve been texting consistently and you suddenly need space or you’re going into a busy stretch, one quick message goes a long way: “Slammed this week but I’ll catch up with you soon.” It takes very little energy and prevents the other person from filling the silence with anxiety or assumptions.
Don’t send multiple fragmented messages in a row when one would do. The rapid-fire approach — where you text in six short bursts rather than one composed thought — can feel chaotic and hard to respond to. Occasional fragments are charming and conversational. A wall of them can feel overwhelming, like you’re talking at someone rather than with them.
Don’t use humor as armor right out of the gate. A little wit is magnetic. An unbroken wall of jokes when someone tries to go slightly deeper reads as deflection. If someone shares something real and your only response is a punchline, you signal that vulnerability isn’t safe with you. It might not be intentional, but that’s how it lands.
Don’t assume tone — ask. If a message feels cold or off and your gut starts spinning out scenarios, it’s okay to gently check in rather than build a whole narrative. “Everything okay? That read a little different than usual” is not needy. It’s emotionally intelligent and often opens up a much better conversation than the silent assumption spiral would.
Bigger Picture
Texting in dating isn’t about performing a version of yourself that seems cool or unaffected. The goal is clarity — letting the other person actually experience who you are through a tiny glowing screen. That means being willing to be a little warmer than feels comfortable, a little more specific than feels safe, and a little more honest than the world of keeping-it-casual usually encourages.
The people who are most magnetic over text aren’t the ones playing it perfectly — they’re the ones who sound like themselves. Genuine, engaged, and not afraid to mean what they say. The skill of being able to come across as the sincere, authentic, conversational you is the real secret.
If you’re still looking for that special someone to share your life with, give Kelleher International a call and allow our talented matchmakers to do the legwork for you. Our coaches will help you navigate the process and make sure you get those initial texts just right! 🙂
