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Texting Rules That Guys Should Learn

6 Things the Average Guy Would Benefit From Learning About Texting in a Dating Context

August 31, 2023

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In case you haven’t noticed, texting is officially the main form of communication daters use nowadays.

It makes sense, too: it’s both more convenient and less nerve-wracking than calling someone up on the phone. With texting, you can send a quick flirty message during your commute, or even make date plans while you’re still at the office.

That said, not all guys reap the full advantages of texting — because, in short, they’re doing it wrong. According to dating experts, there are a lot of things the average guy could benefit from learning about texting.

“Good texting habits offer the momentum a relationship needs to move forward,” says Amber Brooks, managing editor at DatingNews.com and editor-in-chief of DatingAdvice.com. “But one wrong emoji can sour a new romance, and there's a texting etiquette that daters need to follow to build trust and show that they care. Responding promptly and positively to texts from a new match will reinforce that you like that person.”

Read on for some pro tips on how to up your texting game in a dating context.

1. Asking Questions Is Key

“If you're not asking questions, you're not allowing room for the conversation to grow,” says Brooks. “Keep them engaged in the chat.”

Remember: good questions don’t need to be overly complex. You can ask, “Looking for something good to watch — anything you can recommend?” or “What does your perfect date look like?”

Another thing to keep in mind is that open-ended questions are more likely to maintain momentum in the conversation than yes or no questions. For example, try asking: “Where’s your favorite spot to get a drink right now?” rather than, “Do you like beer?”

2. Don’t Lead With Sex

“One mistake I see guys often make with texting is getting too intimate and personal too quickly,” says Brooks.

Brooks’ theory is that men feel more comfortable leading with sexuality over text than they would in person or on the phone because they don’t have to see their crush face to face.

But as a general rule, making vulgar overtures or asking super intimate questions right off the bat can be super off-putting, particularly if you’re a straight guy messaging a woman.

“It's one thing if you're on a hookup site where sexting is more expected, but in everyday circumstances, women aren't going to be DTF any rando in their contacts or match list,” Brooks adds.

While we’re on the subject, Emma Mankey Hidem, creator and host of The Game Show of Love, and founder of The Sunnyside, says you shouldn’t send unsolicited nudes or dick pics.

“Unless you're having an active sext conversation, chances are, she doesn't want that,” she tells AskMen. “No matter how nice you might think your dick is, sending a pic is jarring and goes against consent culture.”

Bottom line?

“It's OK to ask her what she's looking for in a man — it's not OK to ask her what color underwear she's wearing,” says Brooks. “Let her take the lead with flirty sex talk and try to match the vibe she's putting out.”

3. Spell Check Before Hitting “Send”

Dating coaches say they constantly hear from clients that poor spelling and grammar over text is a major turn-off. So, do yourself a favor and scan your messages before you fire them off.

According to Hidem, one misspelled word or punctuation error could lead to confusion or cause an awkward misunderstanding (thanks, autocorrect).

“Grammar matters in text communication because they can't hear your voice—so things like tone, pauses, and the rhythm of your words aren't available,” says Hidem. “Commas and periods go a long way to helping ensure that the person is reading your text as you meant it to sound.”

4. Use Your Texts to Set Up a Date

“One of the most common mistakes I see is that men waste way too much time trying to come up with 'witty lines' or trying to entertain women with their words, and then hoping that it magically leads somewhere,” says Ice White, author of The Message Game.

While it can be fun to flirt for flirting’s sake, if what you really want is a date, don’t forget what the main purpose of texting is in a dating context: to set up that date.

If you spend too much time messaging this person, says White, “You are both developing the habit and the pattern of not meeting. When this happens, the conversation either dies or you just become pen pals.”

According to White, you shouldn't be waiting weeks or longer to make plans; at that point, he says, not only do you risk boring the other person, but they may find someone else who’s quicker off the draw than you are.

Ultimately, once you’ve established that you’re both interested in each other, don’t rely on texting to get to know each other — “That's what the first date is for,” says White.

5. Use Emojis and GIFs — but Not Too Many

Texting is a useful means of communication, but it’s also worlds away from face-to-face interactions. When you’re texting with someone, you can’t hear their tone of voice, see their body language, or sense their intentions as clearly.

“Inflection and meaning can often be lost with virtual communication,” says Katie Schubert, Ph.D., a couples and sex therapist and CEO of Cypress Wellness Center.

That’s why Schubert advises peppering the occasional emoji or GIF into your texts. You definitely don’t want to go overboard here — but leverage them when you need to convey a certain tone or add some flair that showcases your sense of humor.

6. Use Texting to Build Anticipation

“Once you’ve begun going on dates, texting can be your tool for maintaining connection,” says Liv Talley, dating coach and founder of The Sealed Deal, who recommends flirting in a “playful, non-aggressive way.”

The best opportunities to continue building that connection are the post-date follow-up text — as well as the text leading up to the date.

“Sending a quick ‘can’t wait to see you,’ the day of your date both demonstrates reliability (confirming the date is still on) and builds a little innocuous tension to create excitement before seeing each other,” Talley explains.

After the date is over, try shooting her a quick message along the lines of, “Can’t stop thinking about that pasta carbonara — oh, and my date was pretty memorable, too,” or “So, I went out with this girl last night and had the most epic first date ever, what are the chances you think she’d want to hang out again?”

Not only is a cheeky message like this sure to make your crush smile, but it also shows that they’re on your mind and opens the door for planning another meet-up.

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