Do not send her a joke. Send her a short, playful reaction to something she just said: a small exaggeration, a light tease, or a made-up story you both play along with. Text has no voice and no timing, so what works is one quick line that sounds like you and could only have been written to her.
Why jokes fall flat on a screen
In person, a joke lives on your tone, your face and your timing. In text you only have the words. A joke she could have read anywhere lands as a stranger's joke. A long setup with a punchline at the bottom gives her time to decide it is not funny before she reaches the end.
When texting a woman, put a bit of your personality into every line you send. Do not ask the same get-to-know-you questions anyone would ask. Funny in text mostly means being specific and alive to what she just wrote.
Five things that work
Exaggerate what she said. Take a small thing and make it huge.
- She: "I overslept twenty minutes." You: "Twenty minutes. This is how empires fall."
Tease her lightly. A tease is a friendly challenge she can answer. coach teaches the push and pull: a small jab, then warmth.
- She: "I'm a great cook." You: "Bold claim. I'll need to see a pasta under supervision."
The rule of three. coach borrows this from stand-up. Set up two ordinary things and make the third one unexpected. "Do you spend your weekends hiking, reading, or plotting the downfall of your coworkers?" The surprise at the end does the work.
Build a pretend story. A made-up narrative is fun for women because logic is not the point. Make the two of you partners in a ridiculous plan: "We are going to start a heist crew. You plan, I drive, and we only target bakeries."
Pick the right word. Two words with the same meaning give different pictures. "A massive pigeon" is funnier than "a big bird." Read your line once and swap the dull word.
Keep it to one short line
My texting laws apply here as well. Send one idea, or two at most. A paragraph of jokes looks like you are performing, and the effort makes her reply feel like homework.
Keep it casual. A perfect, careful sentence kills the playfulness, and coach says texting should look like you typed the first thing that came to mind.
A quick rewrite
Take a plain text and make it work harder. She says she is stuck in traffic.
- Plain: "That sucks. How long will it take?"
- Better: "Traffic is just the universe testing your patience. How is it going?"
- Best: "Please tell me you have a snack and a dramatic playlist. This is your villain origin story."
The better versions react to her situation, use a specific picture, and take a few seconds to write. They are also short enough to read in one glance.
What falls flat
- Pasted jokes and lines from the internet. She may have seen them, and they say nothing about you.
- Explaining the joke. If you have to add "haha get it", it did not work, and the explanation makes it worse.
- Laughing at your own text. A string of "lol" does not make it funnier.
- Teasing about something that actually stings. Her looks, her job worries and her family are off limits until she shows you otherwise.
- Sarcasm without a smile. On a screen it can read as cold. Add a clear sign that you are joking.
- Joke after joke. After two, ask her a real question, or she starts to feel like an audience.
If she is sad or having a bad day
Do not try to cheer her up with a joke straight away. A quip aimed at her pain feels like you did not listen. Say that you are sorry and ask what happened. Once she has talked, a small, warm bit of humor can help, if she starts it or her mood lifts. Let her set the tone.
What a laugh is worth
A laugh is a good sign, but only one. Check whether she asks you things back and keeps the conversation going. Then use the good mood for what texting is for. My rule is that the text is there to get her to a call or a date, so follow a laugh with a plan: "You owe me a pasta trial. Thursday?"
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.