9 tips to help you develop one of today’s most vital relationship skills
Since I’d last been single, the dating landscape had changed. Over ten years ago, texting on your phone had cost 20 cents per text, and I didn’t know anyone at the time that bothered with that kind of luxury. There also were dating sites, not apps.
But here I was, 32 years old and separated, with profiles on Tinder and Bumble and trying to navigate messages and texts from interested men.
As someone who was on the receiving end of many terrible messages and a Relationship Coach, I know that, today, getting to know someone primarily happens over texts or messages. Texting is therefore a vital skill to learn to catch the interest of another.
Since the majority of my clients are men, I often get asked, “How do I text women? Are there…rules? What do I even say?” Here are my best tips on how to text a new woman you’re interested in:
1. Take it lightly.
A text message is not a marriage proposal. You’re not nailing out the terms of a trade agreement, negotiating a higher salary with your boss, or telling your shadowy awfuls to your therapist. A text conversation should never feellike any of these situations.
Neither should texting with a woman make or break you. If something doesn’t work out, cool. You had some practice with a special hot lady, and you can use what you learned to try again with another special hot lady.
A text should be like putting a penny into a slot machine: low stakes, but could still pay out big.
2. Be polite and respectful.
I’ll likely be refuting a lot of the advice you’ve heard, but let me start withthis one: Women do not prefer assholes over good guys.
Assholes may get women, but do they keep them? Do they build long-term, healthy, mutually beneficial relationships with them? No.
To not be an asshole, make sure you’re always being polite and respectful.She should be someone you want to date, not a Kleenex you throw away once you’re done using it.
3. Text her within 24 hours.
Statistically, there are more single men than women in America. While you’re not texting her, three other guys might, and guess who has a higher likelihood of capturing her attention? One of the guys messaging her while you aren’t.
Most women also expect men to contact them soon after meeting because communication is so easy.
Here is a good text to send:
Hey, it’s Caleb. Nice to match with/meet you today!
Say your name, mention how you connected, and do it before she forgets about you. Also, a “what’s up?” or “how are you doing?” isn’t necessary at this point.
4. Start an actual conversation.
Hopefully, you’re trying to learn about this woman you’re texting, so you should avoid texts like,
How are you?
What are you up to?
Know what she’s probably going to respond with? Hi. Nothing. Good. Working.
These kinds of conversations are boring. Yeah, they can break the ice, but you better change things up quick to hold her attention.
Here are some better texts to send:
What do you think about _______? What are red flags for you in a relationship? What was your favorite ______ as a kid? What are you most attracted to in another person?
Notice that these are all open-ended. You never want to ask her anything that can easily be answered with a simple yes or no. Make her give you more. You can go silly, or you can go serious, but these at least start you actually sharing something with one another.
5. Use her name.
If you haven’t developed a close relationship yet, don’t call her “baby,” “honey,” “sweetheart,” or any other pet name.
You should use her name and only her name in all texts. If you don’t, especially before a date, she’ll likely assume you don’t remember her name and/or be offended.
If you don’t remember her name and can’t find it out through someone else, don’t text her. Move on to someone else you remember.
6. Remind her of something that happened when you met.
Whether you’ve been on just one date or been married for 20 years, a useful skill is reminding your partner of your first meeting or of anything funny that may have happened.
Here are two examples:
“Great meeting you! You made waiting at the DMV actually enjoyable.”
“You definitely made my night. I’m surprised you hung out after I got that drink spilled on me, but it shows how cool you are.”
7. Use proper grammar.
The dating site/app Zoosk found that poor grammar is the biggest online dating deal breaker. They found that “72% of online daters said spelling errors are a turn off and 48% consider poor grammar a deal breaker.”
Users rated poor grammar, misspellings, or improper use of punctuation as someone being “too busy, too lazy, or uninterested.”
It’s too easy to learn whether to use “your” or “you’re,” or to run your messages through a free grammar check like Grammarly before you send them.
8. Follow her lead.
After you’ve been texting with a woman a bit, you should start to get a sense of how she would like to text.
Pay attention to
- how quickly she answers,
- her texting tone,
- how long her texts are, and
- if and how often she uses emojis.
With those things in mind, match her.
Here’s an example of a text conversation that doesn’t match:
Woman: Hey, did you have fun with your friends last night? What’d you guys do?
Guy: Yeah, I did!!! 🥳 Shot pool wit the bros but partied a little too hard, and today, I’m 🤢🤮
Her tone is casual while his is a little…over the top, both with his language and emojis.
A better answer he could have given would have been something like:
Guy: I did! We shot pool and stayed out late, but I’m not feeling so great today. Planning on taking it easy. What did you end up doing last night?
You may not be able to match her texting habits exactly. For example, she may be able to text a lot throughout the day, but you have a job that makes that impossible. Or you prefer to not look at your phone while you’re out with friends or family. Just communicate those boundaries to her, and if she’s a lady worth your time, she’ll respect that.
In any other way you can though, follow her lead and try to match it.
9. Text with a goal in mind.
Ideally, you’re messaging this woman because you a.) want her to become interested in dating you; b.) want to ask her on a date; or c.) want her to keep dating you.
If you’re not texting her with one of those three goals in mind, then quit texting her. That may come across as harsh, but if you’re just looking to “chat” or “be friends,” that needs to be super clear. Otherwise, you could end up stringing her along.
Another reason why you want to text with a goal in mind is because your goal should inform what you text.
Instead of saying:
That class was insane, huh?
You could say something like:
I tried to catch your eye while all that was happening, but I’d really like to talk to you about that craziness. Can I call you, or would you like to meet up?
You’re moving from simple commentary (talking for the sake of talking) to actual connection (moving from a text to a phone call or meeting up).
Just like with any skill, it’ll take practice and experience to up your texting game. But any time you text a woman, see it as more practice. Don’t get too attached to the results, and remember to be kind and purposeful.