Should I Text Him? Before You Hit “Send,” Here Are Some Rules On What To Text Your Crush

To text or not to text — that is the question. Shooting your shot can be a sexy power move that displays confidence, and sometimes, taking initiative is the only way to get what you want. That said, it can also feel risky. What if the exchange doesn’t go as you’d hoped, or worse, he doesn’t respond? If you’ve found yourself wondering, “Should I text him?” — don’t stress. I’m going to offer some easy guidelines for answering that question — plus some tips on how to text your crush.

Normally, my stance is that texting should be for three reasons only: to follow up after a date and say you had a good time, to exchange information (a date, place or time to meet), or for some quick flirtation during the day. That said, the COVID era forced everyone to up their texting game, so now texting and flirting is a great tool in a new relationship to keep pique someone’s interest. You may need to exchange a little more digital banter.

When to text him

You had a great time with him, and you want him to know it.

Whether you recently met up in person or had a Zoom date, if you had a killer time you should definitely let him know. This will reinforce your interest and may offer some reassurance if he’s not sure whether you’re on the same page. As a general rule, I’d advise against texting him five minutes after your date ends. Let him process the date (and maybe even start missing you a little), even if just for a couple of hours, before firing off a message.

In this case, I recommend keeping it short and sweet. If he took you out (either by planning the date or paying for it), you can thank him — and add a little reference to your date, like an inside joke or something you discussed. By ending with “looking forward to seeing you again,” you open up the door for another date and even increase the anticipation.

Something reminded you of him.

If you’re still in the early phases of dating someone, and suddenly you hear a song, spot a hilarious meme, or read a thought-provoking article that makes you think of him — that’s a great reason to text. This is the kind of positive interaction you want to aim for when you’re flirting with someone new — it lets him know that you’re thinking about him.

So, go ahead. Say something along the lines of, “Just saw a trailer for that movie you were talking about — you’re totally right, looks amazing” — or “Just heard this song and figured it was right up your alley. Thoughts?”  Just be sure you’re not texting him every day about things that are reminding you of him, because then these texts start to feel less special (and, of course, more overwhelming). 

You want to ask him out.

Ladies — it’s 2024. You don’t have to wait for him to set up a date, you can take matters into your own hands. It shows that you know what you want, and you aren’t afraid to go get it, which many men would agree is highly attractive. However, keep in mind that you don’t want to always be the one who’s taking initiative. The effort should be 50/50, so if you plan this date, let him take the reins on the next one.

Remember: keep it simple. Ask him when he’s free this week/weekend, or propose a specific activity you’re interested in doing together. Then, lock it down with a date, place, and time.

He’s already reached out, and you want to keep the momentum going.

There’s something oh so exciting about that early phase of flirting over text, when the back-and-forth banter is flowing effortlessly and there’s endless information to learn about each other. Feel free to lean into that. If he’s regularly been sending you texts with funny GIFs, to see how your day went, or just to make conversation, you can totally do the same (provided you’re interested in him, of course).

If you want to keep the momentum rolling but you don’t know what to say, think back to your last convo for some inspiration. Keep in mind that open-ended questions are great because they inspire a response. For example: “Just remembered that story you told me about [xyz] and lol’ing. When will I get to hear more of those?” or “Could really use one of those cocktails we had the other night. You sipping on anything for happy hour RN?”

When to wait

You’re pissed off and want to vent.

Unless it’s your long-term partner, it’s best not to use your date as a sounding board for whatever’s irritating you in life — whether it’s your boss who’s stressing you out or your roommate who’s being totally inconsiderate. That’s because, especially in the beginning stages of dating, you’re trying to keep your interactions as positive and upbeat as possible. You want them to associate you with good vibes — not complaints and frustration.

So, yeah, skip the rants until you’re in a serious relationship and leaning on each other for support. If you really need to get something off your chest, that’s what your BFF (or therapist) is for.

You want to tell him off.

Maybe he hasn’t responded to your text from three days ago, or he ghosted you. Maybe he stood you up. I get it — you’re annoyed, and perhaps even upset. But texting him is not the way to go about confronting him. Since there’s a glaring lack of communication cues (like facial expressions and tone of voice), much can be misconstrued via text.

If you’re really steaming about something he did, start by giving yourself some time and space to cool off before reaching out. Then, once you feel like you can express your feelings calmly, reach out to ask if you can talk face-to-face (whether in person or over FaceTime/Zoom). It won’t do either of you any good if you attack him over text — in fact, it’ll likely only put him on the defensive, and then you’ll never reach a place of understanding or get the apology you’re looking for.

You’re inebriated.

Alcohol lowers your inhibitions. That’s just a fact. So, if you’ve had some liquid courage, it makes sense why you may feel suddenly tempted to reach out. But if you’ve had more than one drink, I’d advise holding off. The problem with texting someone while you’re drunk is that there’s always a chance you might say something that your sober self seriously regrets tomorrow (again, because your inhibitions are impaired). Waiting for those cocktails to wear off means you’ll be more clear-headed, and in a better position to decide whether it’s actually a good idea to text this person or not.

You already reached out today, and he hasn’t responded yet.

I don’t believe in playing games (unless you want to date someone who’s immature, emotionally stunted, and only likes the chase). That said, if you’ve already texted a guy you like and he hasn’t gotten back to you yet, there’s no need to send a third or fourth message to try and get his attention. In fact, it might do the opposite. When he sees a string of texts on his lunch break, he might feel so overwhelmed that he’s less likely to respond.

There are lots of reasons why he might not have texted you back yet. Maybe he’s been super busy lately, or maybe he’s not that interested. Only time will tell, so just be patient. After all, you don’t want to be the only one who’s putting any energy or effort into texting — and by giving him a chance to meet you halfway, you’re setting up a dynamic where you’re both equally invested.

He’s your ex, and you’re missing him.

Without a doubt, this is the most complicated scenario of all. I’m not going to say never text your ex, but for the sake of your own emotional and mental well-being, there are only very specific circumstances under which you should reach out. For example, if you need to coordinate retrieving some belongings, or you need to discuss some logistical issues about your shared pet — then feel free to shoot them a text if that’s the most convenient way to get in touch. If you’re just feeling lonely, resist the temptation to seek out comfort from a former flame and remind yourself that there was a reason (and possibly more than one) that you broke up.

What about if you want to get back together? Well, in that case, you have some serious soul-searching to do. Sending a text could open up a whole can of worms that may make it even more difficult for you to heal from the split and move on with your life. Instead, give yourself some time to figure out why you’re missing them, and whether or not you’ve actually worked on any of the issues that were plaguing your relationship. If nothing has changed between you two, you’re just going to keep running into the same problems over and over again (and thus, get trapped in an on-again, off-again situation).

In other words, it’s really important to get honest with yourself when figuring out whether reconnecting with an ex is a healthy choice. Otherwise, you could end up even more heartbroken than you were before. Pro tip: If you’re feeling lonely, reach out to a trusted friend instead. That way, you get the love and support you’re looking for without the risks and emotional baggage.

The bottom line? It’s best to not overthink this. If you’re into him, he seems into you, and you have a positive reason for texting him, go for it. Above all, be yourself, be courteous and considerate, and be upbeat. If your texting styles simply don’t align, then you’re probably not a good match after all — and it’s on to the next guy who will not only accept your digital communication habits but actually appreciate them.

If you need help knowing what to do in these dating situations, you can always sign up for date coaching or a one off session. Fill out our confidential profile here.