The Worst Text Messages to Send to a Woman You Are Interested In

11th Hour Matchmaking, Dating, Scottsdale, Phoenix, Tempe

The Worst Text Messages to Send to a Woman You Are Interested In


Ah, the text message.

For many people, text messaging has virtually replaced the phone call. A good text will tell her you’re thinking of her. It’ll bring a smile to her face and keep you in her mind.

It can be an incredible tool for growing a romance.

But text messaging has its limits. Send the wrong text to the woman you’re interested in, and suddenly it’s game over.

If you say something wrong in person, you have the chance to smooth it over. Do it in a text, and you’re not going to get another chance.

Here are some texts you never want to send to a woman you’re interested in.

Asking for a date

“Hey, I’d love to take you to dinner sometime. What do you think?”

Never ask for a date over text. Even if you’ve been texting back since a first meet, this is a no go.

Asking for a date over text is a cop-out. It’s impersonal. If you want a woman to think of you as a sophisticated, mature man, then you need to make the call… the phone call.

Asking for pictures.

“I can’t wait to meet you. I’d love some pics to hold me over.”

Um… No. Not only is this juvenile and creepy.

Even worse is if you suggest that those pictures show more skin than clothing.

Just checking in


Yeah, this isn’t a text. It’s a cry for attention.

There is no message here; she has no idea if you want her to call how you want her to reply.

It’s one thing to do this as part of your flirtation once you know each other. It lets her know you’re thinking of her.

But until that time, it feels more like desperation.

Asking about her clothes

“So, what are you wearing? Is it hot?”

Seriously, see the one about pictures.

Some people try to justify this one by saying they’re trying to make her feel desired. But it’s creepy and stalkerish.

It’s a text you can send to your established significant other or your wife while you’re away on a trip.

But if you’re in the initial stages of dating, this text is going to get your number blocked.

Sexting messages

You know what we mean. This one goes with the clothing texts. Don’t do it.

Unless you’re in a long-term relationship, this is inappropriate.

Abbreviated words

“What r u up 2 2nite?”

Teenagers talk like this. But you’re a grown adult who hopefully has full command of the language.

A woman who sees this message wonders if you’re immature. Or lazy.

Announcing your arrival


So? If you’ve set a date to meet, she’s expecting to see you. She’ll notice you’re “here” when she sees you.

This message is just a filler that is more annoying than helpful.

And if you’re picking her up someplace, you don’t text from the car. You walk up to the door and knock like an adult.

Canceling your plans

“Can’t make it. Rain check?

Like asking for a date, canceled plans need a call.

She’s set aside time in her schedule for you. She may have already begun getting ready for your date.

She’ll understand that sometimes things happen. The least you owe her is a phone call to cancel the plans and to reschedule right away.

Changes in plans

“Running late.”

Seriously? You have the phone in your hand, just call her.

Tell her what happened and when she can expect you. Don’t leave her hanging with a vague message of “running late.”

Looonnnnnngggggg Messages

If a message is longer than fifteen or twenty words, it’s too long.

Texting was created for short messages to save time – not to write your novel in her message inbox.

Long texts are annoying and take time to read. Plus, the longer the message, the more chance that something will come across wrong.

If you have more than a dozen words to say, call her.

Asking about your relationship

“Do you like me?” “Are you mad at me?”

You’re not in high school. A text is not the place to ask for the status of your relationship.

If she accepts a second date, she likes you. As you get to know each other, you’ll know what she thinks.

And if you think you’ve upset her, be an adult and call.

An involved question

“How do you feel about…”

If a question requires more than one message to answer, save it.

Don’t use text to interview the woman you’re interested in.

Any message that needs an in-depth or long answer is better left for a call… or your next date.

Offensive jokes

This one needs no explanation. You never know when an offensive joke will go over like a lead balloon. So, don’t send these via text. Ever.

If you really must test her boundaries on these, do so in person. At least then you can do damage control if you offend her.

Anything at all while you’re intoxicated

You’re not going to make a positive impression on a woman you’re interested in if you’re inebriated.

The last thing you want is to wake up the next morning and see what you wrote.

And she didn’t want to see it at all.

In short….

If you’re not sure if it’s a text situation, don’t text.

The best thing is to call. It’s far more personal, and you can have a real conversation. You’ll learn much more about each other and improve your relationship.