Say something specific, tease her a little, and share a small detail about yourself instead of firing off questions. A boring text is one any man could send to any woman. If you are messaging your matches on the dating apps, a message that only you could have written is already ahead of most of what she receives.
What makes a text boring
Boring does not mean rude or even bad. It means interchangeable. "Hey, how's your day?" could go to a hundred women and need no changes. She has no reason to answer it with more than "Good, you?"
Three habits cause most of it.
- One-word messages. "Hey," "lol," "nice." They give her nothing.
- Question after question. Every message ends with "what about you?" and she starts to feel like she is being interviewed.
- Reporting your day. "Just got home, about to eat" is a status update, not a conversation.
If you recognize yourself, you are not alone. The fix is small.
Say something she can react to
A good text has a hook. That can be a guess about her, a mild tease, a strong opinion, or a small story.
Instead of "What do you do for fun?" try "You seem like someone who has strong opinions about brunch. Am I right?" She can answer yes, no, or argue. All three give you more to work with.
Instead of "How was your weekend?" try "I tried to make pasta from scratch on Saturday and it looked like a crime scene. Did you do anything more successful?" You have told her something real and funny, and the question that follows now has a reason to exist.
The idea is the same as in person. a dating coach advises making the interaction yours by adding your own personality instead of asking her to supply all of it. A text with a bit of you in it gives her something to hold.
Tease, lightly
Playful teasing is one of the fastest ways to stop being boring. It works best on something small that she said, or on a harmless contradiction.
If she says she is a morning person, you might send, "Of course you are. You probably enjoy those people who say hello on elevators." Keep it warm. If you tease her, make sure she can laugh at it, and never aim at anything she is sensitive about, such as her looks or her job.
If a tease gets a flat reply, back off and move on. Do not explain it, and do not apologize at length.
Share before you ask
When you do ask a question, give something first. "I have been trying to find a good taco place near me. I think I found one. What is your go-to food?" works better than "What is your favorite food?" because you have opened the door.
This also keeps you from sounding needy, because you are contributing as much as you are requesting. It is a habit worth building, and it fits well with the idea that a conversation is a trade.
Match her length and speed
If she writes two lines, do not send a paragraph. If she sends one word, do not respond with a long story. Matching her rhythm, roughly, shows you are in tune with her. A man who writes ten times more than she does looks eager, and a man who writes ten times less looks bored.
You do not have to copy her exactly. Aim to be in the same range. If she opens up and writes more, you can too.
Keep your texts short
Most good texts are one to three sentences. If you have a long story, save it for the date, where you can tell it with your voice and she can react in real time. A paragraph she has to scroll to finish is a poor first impression.
Every text should lead somewhere
Texting is a means to an end, and the end is a date. A man who exchanges small talk for two weeks and never suggests meeting becomes a pen pal. After a few easy exchanges, move toward a plan.
Try something like: "This is more fun than I expected. We should do this in person. Thursday at 7, a good coffee place near you?" Name a day, a time, and a type of place.
If she does not respond to the idea, do not chase. Wait a day and see whether she brings the conversation back up. If she does not, move on.
What not to do
- Do not send the same opener you found online. She may have seen it.
- Do not double or triple text when she has not answered. Wait.
- Do not send a long message when she has sent a short one.
- Do not text late at night just to say hello. It reads as boredom.
- Do not overuse emoji to cover a dull message.
One test before you send
Read the message and ask yourself: could another man send this exact line to another woman? If yes, change one word to something only you would say. A small, specific detail turns a dull text into one that sounds like a person.
Written by Matthew Stevens, Co-Founder & Head Coach. More than half a decade coaching men across the US and worldwide.
Everything here comes out of real coaching work: the approaches, dates, texts and profiles we go through with the men we coach.




















