Talk about things she can react to. Her day with a small twist, a low-stakes opinion, a joke that comes from something she told you, and a plan for the two of you all work. Interviews, life stories and "what are you doing" do not. Each text should give her something easy to answer, and then you answer her back, so it feels like a conversation and not a questionnaire.
Start from what she gave you
Whatever she told you last is your best material. If she said she had a presentation, ask how it went. If she said she is training for a race, ask what the hardest part is. This is the easiest way to keep a conversation going, and it shows her that you listen.
A generic "what's up" gives her nothing to work with. "Did the boss survive your presentation?" gives her a small story to tell.
Topics that work
Here are reliable ones, with an example of each.
- Her day, with a twist. "Is today more productive adult or barely functioning human?"
- Small opinions. "Settle this: is a hot dog a sandwich?" Or: "What's a movie you'll defend even though everyone hates it?"
- Food and places. "Best meal you ever had by accident?"
- Plans and trips. "If you could skip work and go anywhere this weekend, where?"
- A shared moment. Bring back something funny from when you met.
- A short story from your own life. One fun detail, two sentences, and a question back to her.
Preferences make good topics because they reveal personality without being heavy. Specific questions beat broad ones. "What's a song you replay when nobody's watching?" gets a real answer where "what music do you like" gets a shrug.
Send a photo or a link
A picture of something funny you saw, with one line, gives her an easy way to answer. A dog in a sweater, a terrible menu translation, the sign outside a shop. Keep it tied to something she said or something you both would find funny.
Do not send a flood of links or memes. One at a time gives her room to respond.
Funny and flirty
You do not need to be a comedian. Tease something she said, not her looks.
If she says she owns twelve plants, write: "Twelve plants? Your living room is one watering can away from a farm." If she says she always orders dessert, write: "So you say you are full, then eat half my cake."
A little teasing creates warmth and play. Keep it light, tied to something she did, and never aimed at her body, her job or her family. If she teases back, you can add a little more. If she does not, stay where she is comfortable.
Late at night and when you are bored
Late night is fine for a lighter, sleepier tone. Do not suddenly go heavy or suggestive when nothing earlier was flirty. The sudden jump is the problem.
If you are bored, do not text "I'm bored." It gives her no reason to reply and says you picked her because you had nothing else to do. Send something specific: "I just saw a guy walk a cat on a leash. Do you think that is cool or sad?"
Topics to leave out
Some subjects drag a text conversation down early:
- Long complaints about work or your week
- Your exes and old dating drama
- Politics as a fight
- Heavy personal stories you would not tell a coworker on day one
- Rapid-fire questions that sound like an interview
One short complaint is human. Ten minutes of them makes you background noise. One sentence about an ex is enough. If a topic makes her go quiet, change it.
Match her effort
Look at how much she writes. If she sends a short line, send a short line back. If she sends a paragraph and two questions, give her more. You are not scoring her replies, only keeping the balance so neither of you feels chased.
Do not send several texts in a row because she has not answered. One clear text is enough.
Move toward meeting
Texting is a good way to find out if you enjoy each other. It cannot replace meeting. After a few good exchanges, suggest a simple plan: "You are fun to talk to. Coffee Thursday or Saturday?" Then stop typing and make the plan real.
The best text conversations give her a reason to look forward to the next one, and then lead to a table where the two of you can talk.
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.