How to Flirt Over Text With a Match Without Being Creepy

Most men solve this problem by not flirting at all. They keep the conversation friendly, polite and safe, then wonder why she took three days to answer and never suggested meeting.

The opposite failure is louder and better known. A compliment lands wrong, the temperature jumps, and she leaves the conversation open without replying to it again.

Both come from the same confusion. Men think the line is about how bold the message is. It is not.

Flirting is reacting to her. Creeping is announcing what you want.

"You've got a dangerous amount of confidence for someone who just admitted she cannot parallel park" is bolder than "you're gorgeous", and it is nowhere near the line, because it is about something she just did.

"You're gorgeous" is a statement about your reaction to her photos. She has no part in it. She did not do anything to earn it and there is nothing to say back except thank you. Two or three of those in a row and she can feel that the conversation is happening at her rather than with her.

Every rule below is that one idea applied.

She tells you she is a nurse who cannot stand the sight of blood in films. She tells you she is training for a half marathon and has not run since April. She tells you her flat is full of plants she keeps killing.

Each of those is an invitation. She handed it over so that you would do something with it.

"So you're the world's most dangerous plant owner. How many casualties are we talking?"

That is flirting. It says you were listening, it has a bit of edge in it, and it gives her an easy way to play along. Nothing in it is about how she looks and nothing in it is about what you want from her.

Not every compliment is a problem. The difference is whether she chose the thing.

Her face is not a choice. Her body is not a choice. Her taste in music, her job, the fact she went travelling alone, the dry way she writes, the photo she clearly picked on purpose because it makes her look slightly unhinged: all choices.

"You have an unfair number of good restaurant opinions for someone who lives that far from town" is a compliment that reads as interest in her. The same sentiment aimed at her body reads as interest in yourself.

If you want to say something about her looks, wait until the date, say it once, and move on. In text it does almost nothing except raise the temperature you cannot control.

Two men can send the exact same words and only one of them is creepy, because tone does the work.

The warm version is light, brief and unbothered. It does not care very much whether the line lands. It is happy to be wrong.

The heavy version is a bit too careful and a bit too much. It repeats. It explains. It adds a wink so she knows it was a joke. It asks whether it was too much. That last one is the giveaway, because now she has to reassure you before she can carry on.

The simplest rule: send it once, at normal volume, and let her decide what to do with it.

Flirting is a back and forth. She matches your temperature, you go a step further, she meets you there.

What goes wrong is men climbing by themselves. She sends a friendly reply, he sends something suggestive. She answers politely, he goes further still. Nothing in her messages is coming back at the same heat, and he keeps going anyway.

Check whether she is playing. Is she teasing you back? Is she adding something, or just receiving what you send? If she is not coming with you, drop back to where she is comfortable and carry on. You lose nothing by doing that, and she relaxes immediately.

Commenting on her body before you have met. It changes what the conversation is for.

Saying she is different from other girls. It sounds like you have decided who she is from six photos.

Long messages about how well this is going. Naming it too early puts weight on her she did not ask for.

Sending it late at night when nothing before it was flirty. The hour is not the problem. The jump is.

Flirting over text is not a way of winning her over from a distance. It is a way of finding out whether there is anything there, quickly, so you can suggest a drink while it still feels warm.

When she plays back, use it. "Right, I need to see whether you're this argumentative in person. Wednesday?" That line only works because the conversation earned it, and it stops the flirting from turning into weeks of texting that never leaves your phone.

The hard part is that nobody can hear their own messages properly. You know the voice you wrote it in. She only has the words.

If your conversations keep going flat, or keep cooling right after you try something bolder, the wording is rarely the whole story. It is usually tone: slightly too eager, slightly too careful, slightly too keen to be liked.

That is the kind of thing somebody spots in ten minutes with your real conversations in front of him. A call with a coach who reads what you actually sent will tell you more than another month of guessing which line went wrong.