The Dos And Don’ts Of Texting Someone You Want To Date

Dating is a curious beast at the best of times. Throw in a global pandemic and everyone’s got their heads in their hands wondering how the hell to navigate this unchartered territory safely. One thing we should get straight, however, is the mixed (and often bad) advice we receive when it comes to texting someone you’re interested in.

Seeing that we’re all going to be dating from afar for a while longer yet, it seems relevant that we learn how to master the art of romantic texting properly. So, here are some tips that will actually help you out.

Don’t “wait x days” to text them

The first text is always the hardest. How long do you wait to message that cute guy from the gym? If you ask around, some people will tell you to wait for “this many days” before you make contact, but that strategy is flat-out silly. Dating columnist Dr Nerdlove told us that you should always touch base sooner rather than later. If you don’t text them relatively soon (or sit around hoping for them to text you first), a couple things can happen: that cute guy at the gym will either forget about you and that he gave you his number at all, or he’ll assume you’re not actually interested. Nerdlove recommends you text them in the same day or night to keep the emotional momentum going and to solidify yourself in their memory. You’ll become “that cute girl from the gym” instead of “some girl that I guess I talked to other day?”

What you say in your first text message is important (more on that later), but it isn’t nearly as important as you actually reaching out. Don’t be afraid of the initial text message. As online dating coach Patrick King explains, they have already given you their number because there is some mutual attraction there, so you don’t have to stress as much about the possibility of rejection. When you do send that first text, however, Regina Lynn, the author of The Sexual Revolution 2.0, suggests you follow the same etiquette as phone calls. Don’t text him at odd hours, like late at night or really early in the morning. Texting the cute guy from the gym when he’s trying to sleep will turn that “yay she’s texting me!” moment into “why is that girl waking me up?” Not a great first impression.

Don’t ever just text “Hey/Hi/Hello”

This was by far the most common advice you’ll find: don’t just text someone “hey.” In fact, if you browse some online dating profiles you’ll probably find people sharing the same advice. While writing the book Modern Romance, comedian Aziz Ansari and Dr Eric Klinenberg, Professor of Sociology at New York University, organised hundreds of focus groups to decipher the modern dating landscape. When they asked the focus groups about their personal texts, they found that participants unanimously agreed that the “hey” text is a bad idea.

As Ansari and Dr Klinenberg explain, the “hey” text seems like a perfectly harmless message to send, but that one word says a lot more than you realise. It’s generic, dull and lazy. It makes the recipient feel like they’re not very special or important, and it makes you as the sender seem the same way. No information is being shared, nothing is being asked of the recipient, and it’s incredibly easy to ignore. A good first text will explain who you are and reference your previous interaction in some way.

Focus your early texts on making plans

After you’ve made contact, focus your early text conversations on making plans. It’s exciting when that cute girl from OkCupid seems way into texting you, but as Christine Hassler, the author of 20-Something, 20-Everything, suggests, too much pre-date texting smothers any spark you might have on your actual first date:

That can make you over-think what you say and do on the date, instead of being your natural self. It’s like you’re on your second date in terms of info, but you first date in terms of physical chemistry, which can make things awkward.

Emily Morse, the host of the Sex With Emily podcast, calls this problem “premature escalation”:

Since our whole world is so instant now, people can craft entire personas through their slew of texts. . . by the time you meet your partner for an actual date, you’ve built up this whole image and fantasy in your head of who you think they are, and then they turn out to be totally different.

While making plans, be as direct as possible. During their focus groups, Ansari and Dr Klinenberg also noticed a texting trend they dubbed the “secretary problem”, where potential couples would spend so much time trying to “pencil each other in” they would burn out and the spark would fizzle before the first meetup. We asked Vanessa Marin, licensed marriage and family therapist and Lifehacker contributor, how to avoid the “secretary problem”, and she said it’s all about being specific:

Make specific plans. It’s easy to make a vague commitment via text, like, “let’s talk Friday about doing something this weekend.” If you’re genuinely interested in the person, suggest a specific day and time for your date.

Don’t text “Wanna do something this weekend?” Instead, say “Hey, I’d love to take you out for dinner Wednesday night.” If you can make a callback reference to a previous interaction — like a restaurant or type of food you both talked about — it’s even better. Say something like “Hey, how about dinner at that restaurant we talked about on Wednesday night? Around 8-ish?” As Chelsea Clishem at Patti Knows advises, texting should be the prelude to a conversation, not the conversation itself.

Keep calm and don’t be pushy

Don’t make your early text messages an interview. Not only will you use up all your conversation starters before you actually meet that “guy your friend set you up with”, you’ll probably create unnecessary stress for yourself. King suggests that texts dependent on responses will leave you feeling anxious and insecure. Did they get my text? Why aren’t they answering? Did I offend them somehow? Are they ignoring me? The fewer direct questions you send their way, the fewer responses you have to stress about.

Also, just because the guy you’re being set up with doesn’t answer right away doesn’t mean he’ll never answer you. Nerdlove recommends you always give them plenty of time to respond and always avoid being pushy:

Unless the two of you are already having a conversation – having moved from online dating to texting, for example or from when you met – text sparingly. If a conversation starts, great; if not, don’t stress it. Some people don’t text much… If you *are* already talking, follow the flow of conversation. Don’t try to force it; if things taper off, let them. It’s much easier to make someone lose interest by being too pushy.

Good text conversation, according to Nerdlove, is like a tennis match. When you serve the first text, wait for him to return the ball and send one back:

If you’re doing most of the talking or all you’re getting back are one or two word responses, then you’re pushing too hard and they’re losing interest. Dial it back (without calling attention to it – “Well, I’m clearly boring you” is annoying *and* passive-aggressive) and let them re-initiate.

If he doesn’t, wait at least a day before you send another. A good rule of thumb is to keep it to one text per response per day. If your conversation has seemed to completely die off, and you’re worried the guy you were set up with has lost interest (or forgot about your upcoming date), Nerdlove mentions that it’s OK to reach out cautiously. A text like “looking forward to seeing you tomorrow” isn’t a bad idea. It helps confirm that your date is still on and it shows your interest in a way that doesn’t come across as being overeager or pushy.

Grammar and spelling matter more than you think

While it’s debatable whether grammar and spelling matters in texts overall, you’re better off using proper English in your initial texts with someone you’d like to date. Ansari and Dr Klinenberg said that bad grammar and spelling was considered a turn off in every interview they did with focus group participants. Generally, interviewees explained that it made the sender seem unintelligent and lazy.

Avoid using shortened “chatspeak” like “l8r”, “2day”, “b4”, and “plz”. It might be fine with your friends, but it will make a bad impression on someone you’re romantically interested in. Chatspeak can also be easily misunderstood if the receiver doesn’t know the abbreviations you use. All in all, stick to correctly-spelled words and clear language — at least at first. Don’t text the girl from work “fyi i frgt have an appt l8r idk if i can meet 2day.” Say something clear like “I forgot I have an appointment this afternoon. I’m so sorry, do you mind if we reschedule our date for tomorrow?”

The punctuation you use matters as well. Research suggests that using periods to end all of your messages can make them seem “too final” and insincere. At the same time, an exclamation point has been shown to make messages seem more sincere. For example, there’s a big difference between the texts “I’m fine.” and “I’m fine!” when you’re on the receiving end. The first almost looks angry, while the other one seems light and carefree. Also, if you’re asking a question, always use a question mark to avoid confusion.

Always mind your tone

As Nerdlove explains, tone is incredibly difficult to gauge via text. Even if you’re using emoji and emoticons, you need to be careful with jokes, teasing and even flirting. You may think you’re being flirty and silly, but they might think you’re being serious and crossing the line. Use the other person’s real name early on, not nicknames or pet names. Yes, you want to let the cute guy from the gym know that you’re attracted to him, but only referring to him as “handsome” or “gorgeous” could be taken the wrong way, or worse, make them think you forgot their name.

If you want to use humour, Nerdlove suggests the safest route is to callback something from a previous interaction. For the cute guy from the gym, make a joke about the gym (or working out) since that’s how you met. You should be especially cautious, however, of using sarcasm in your texts. It rarely reads as well as it sounds in your head. If you really want to try, however, a study published in The Quarterly Journal of Experimental Psychology suggests that using some emoji, emoticons or an ellipses can help. A text like “I can totally out-bench you ;-)” reads a lot better than the matter-of-fact “I can totally out-bench you.”

If you have a feeling something might be taken the wrong way, stop yourself. Laurel House, the author of Screwing the Rules: The No-Games Guide to Love, suggests you take another look at your text before you send it and read it out loud to yourself. When it comes to sticking with safe subject matter, a good rule of thumb is if you wouldn’t talk to them about something in person, you shouldn’t talk about it over text. Lastly, keep your selfies and other pictures to yourself unless it has been okayed by them. Never send unsolicited anything.

Don’t overthink response time

While the world of romantic texting isn’t a large field of study (yet), there is some research that suggests you shouldn’t answer every text immediately upon receiving it. For Modern Romance, Ansari and Dr Klinenberg found there was a general cultural consensus that you shouldn’t ever text back right away. According to their focus groups, texting back immediately can potentially make you seem overeager or desperate. It may seem a little strange to intentionally blow off a text, but it’s possible it will make you more desirable — at least in the short term. All that being said, Marin recommends you don’t overthink it too much:

So many people waste a lot of time and energy trying to figure out the exact right amount of hours or days to wait before responding. The thing is, we’re all so attached to our phone that we know the person has seen our message. Sure, you can wait a few minutes so as not to appear completely overeager, but just respond when you see the message.

It doesn’t hurt to wait a little bit if you’re really worried about coming across as overeager, but don’t adhere to some bizarre rule about “always waiting twice as long as they took to respond” or “always waiting three minutes to respond”. If you want to respond, respond. If you’re keeping your early text conversations focused on the right things (like making plans and carefully showing your interest in them), you shouldn’t have to worry about seeming overeager anyway. If things go well, after a few dates you’ll develop your own texting repertoire between the two of you and it won’t matter.

Know when to stop texting

OK, so OkCupid girl hasn’t responded to your last text for two days. What do you do? Dating expert Joan Actually at the Zoosk YouTube channel suggests you shoot them a text that doesn’t beg for an answer to feel things out. Send something like “Just finished Making a Murderer on Netflix. It’s crazy!” or “On my way to the water park. So excited!” If you get any questions or other responses, they’re probably still interested. If not, it may be time to move on. When it comes to throwing in the towel, Nerdlove shares his golden rule:

One unreturned text could be tech problems. Two unreturned texts could be bad luck or someone being busy. Three unreturned texts is a message. Move on.

Of course, if you’re on the other end of things, it’s definitely polite to at least say something — especially if you’ve already met in person before. Marin explains that you should avoid “ghosting”, or completely avoiding any contact with the other person:

Don’t ghost. Texting is so easy and non-confrontational that there’s really no excuse for ghosting. If the other person is halfway decent, treat them with respect and let them know you’re not interested. Keep it simple with something like, “thank you for the invitation but I don’t feel enough of a connection.”

If they continue to bug you after you’ve said you’re not interested, however, ignore them or block their number.

This article has been updated since its previous publication.