How Can I Get Better at Communicating Via Text?

Key Points

• A good rule of thumb for text messaging is to use phrases or short sentences—you're not writing a novel.
• Establish clear expectations about what you're willing to do or not do with your time and energy.
• There are no rights or wrongs in sexting but there has to be consent.

I've had a phone since I was 12. However, even with 17 years of experience, texting hasn't gotten any easier.

Sure, the method of typing is simpler on an iPhone but I still spend way too much time typing, deleting, rewording and deleting again, because sometimes you need to make a point without being passive-aggressive. I want to hold my own without starting an argument. I want to get a complex sentiment across in a concise, clear way.

No matter how much of a wordsmith you may be when having actual conversations, giving speeches or writing essays, stringing words together in a text still presents a challenge for many of us. As I found in an article I wrote earlier this year, some folks "sense-check" texts with others before they send them.

This is all before you factor in dating, relationships and breakups. How many of you, for example, decided not to text the amazing person you met last night because you couldn't work out how to ask them out via DM?

Let's take a deep dive into how to communicate via text—especially for dating—in a compassionate, respectful way that also ensures we hold our own and make our point.

How can we stop waffling and be more concise?

"Think about what you want to say before texting. What's the one thing you want to get across? Think about the point and avoid any extraneous detail that will get in the way. You don't want to confuse people or have those details muddy the message," said Karen Laos, a communication expert in San Francisco.

"A good rule of thumb is to stick to phrases or short sentences and remember that a text should not be a novel," she said. "People are reading things quickly and if your text is paragraphs long, it's competing with already short attention spans."

It's a great communication tool for getting to know someone, but keep in mind—how you text and how you present yourself in person should be aligned.

It's tempting to over-explain but we live in a busy world. None of us wants to plow through lines and lines of interior monologues.

"We often feel the need to explain ourselves and most of the time that isn't necessary," Laos said. "Be brief, be bright, be done."

If you have a lot to say, Laos recommended sending one text and including a space separating each of your points. 

"Keep your texts limited to two to three lines, ideally, but if you have to do a longer one, then remember to space out those messages with an actual space in between, so you don't overwhelm the reader with a data dump of information that they won't read anyway," Laos said.

That return key is your friend. No one needs an incoherent brain dump.

How can I—respectfully—ask someone out via text?

"The question to ask is, 'Do you respect the person you're asking out?'" said Jordan Marks, L.M.F.T., the founder and principal therapist of Mind-Body Healing Center in Santa Monica, California. "Do you know them well enough to have determined whether or not they want to go out? Has there been any conversation beforehand that presumes there is an opening?"

Consider if there has been a progression.

"From respectful pleasantries to finding out more information to determining readiness to eventually asking them out," Marks added. "If you respect them as a person, be clear and direct when you are ready. Try, 'I have really enjoyed our conversation so far and I'd like to meet you in person to go out on a date. How does that sound to you?'"

Remember, just because it seems like there's an opening, that doesn't mean there is one. Also, just because there was once an opening, that doesn't mean there will always be one.

If the other person seems hesitant, they probably are. If they change their mind, it's important to respect that.

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How can I respect someone's boundaries when texting?

Boundaries establish clear expectations about what you're willing to do with your time, energy and body. Respecting those same boundaries over text is crucial when dating (and in life).

"Think about how you would treat the person you're chatting with on an app or whoever you're dating as if you were with them in person," said Eva Gallagher, a resident dating expert at Plenty of Fish, Vancouver, Canada. "Read carefully to ensure you're picking up cues they're sharing about their personal boundaries and make sure you're also clearly communicating yours."

She gave an example to illustrate her point.

"If you're someone who requires a good morning text and the person you're dating says they don't look at their phone until midday, have an open dialogue to ensure both parties' needs are being met," Gallagher said. "Also, if you're unsure about any boundaries or attempts to communicate boundaries, asking them and clarifying can go a long way and help them feel safe and comfortable expressing their boundaries and needs back to you."

There are tools we can use to help us when we're dating or just communicating with friends.

Laos noted that it's best to communicate respectfully and let kindness always be your guide.

"Show interest," she said. "Keep your texts short. Don't speak in acronyms and buzzwords. Avoid using sarcasm, as that doesn't translate well over text. Emojis are a great way to show kindness and fun, allowing you to convey meaning beyond the written word.

"Additionally, state your intention upfront, such as, 'I know tone doesn't always translate in text. I want to say up front that I care about you and my intent is always to be considerate of your feelings.'"

What about sexting?

It's the elephant in the room that we simply have to talk about.

"Plenty of Fish recently coined the term 'consexting,' which emphasizes the importance of discussing boundaries and receiving consent before engaging in sexting with a partner," Gallagher said. "Once you both consent, discuss openly and clearly what your likes and dislikes are, as well as what you're both comfortable with, and stick within these parameters."

Marks noted that as long as there is consent between partners, there are no rights or wrongs when it comes to sexting.

"When sexting, make consent sexy," he said. "Find the yes in the other by seducing information. Take it slow and push the boundaries, while looking for cues to keep going or to slow down. When sexting, as in sex, you are looking for a mutual experience, as opposed to masturbation. To ensure the experience of sexting is mutual, stay in the flow with the other and enjoy the ride."

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How can I be my best self in text arguments?

The short answer to being your best self in a text argument is to not get into an argument in the first place.

"My first suggestion would be to avoid any arguments or conflicts over texts," Laos said. "That's the time to pick up the phone and have an actual conversation. Tone is so hard to read in writing and lots of misunderstandings can happen."

She provided some example texts you could use if conflict arises:

• "Let's have a conversation about this. I'll call you."
• "This mode of communication isn't working for me. I'm going to call you."
• "Tone is challenging over text. Let's talk."

She also gave some example ways to respond if you're feeling pressured over setting a boundary:

• "I won't go into more on that, but here's what I will share with you."
• "I'm not comfortable sharing that/talking any further about this."
• "When you're free to talk about this, call me. I'm done with texting anymore about this."

"If someone keeps pushing you to respond, stop texting back," Laos said. "It can be hard because we want to keep defending ourselves, but the best thing to do is stop. Those who want to argue need someone to dance with, and if you get off of the dance floor, then you set a healthy boundary."

"Usually, text arguments don't go well," Marks said. "If you have to text, try a different way. Voice texting, video texting like the video chat app, Marco Polo, and so on. When your voice is heard or you are seen, you're far more likely to get the desired result."

The bottom line

"During the talking stage [when dating], texting can be really fun and it has opened the door for a lot of people who may otherwise be more shy and less inclined to strike up a conversation in person," Gallagher said. "It's a great communication tool for getting to know someone, but just keep in mind that how you text and how you present yourself in person should be aligned. Let people get to know you for you, because this will not only boost your self-confidence but will also help you to meet and connect with people who are best suited for you."

If you really struggle with texting in general—whether in a dating scenario or more generally—Laos suggested you start thinking outside the (text) box.

"Use the voice memo feature so you can speak your texts," she said. "When writing texts, keep your sentences short. Use ChatGPT to help you. It's a great resource to help you communicate with clarity and impact."

Many people find texting difficult. But there are tools we can use to help us when we're dating or just communicating with friends. The goal is to hit that "Send" button without going into paroxysms of anxiety immediately after—and without causing hurt, offense or discomfort.