Should I Text Him First? 3 Times You Should and 3 You Shouldn’t

A woman wondering, "Should I text him first?" while looking into her phone outside.

You’d think adding an additional way to communicate would be helpful for dating in the 21st century, but it’s really just opened up a bunch of new problems. You can’t properly assess tone, and if everyone is on their phone all the time, why isn’t he responding soon enough??

For your own sanity, follow these tips to figure out when you should and shouldn’t text him first:

DO: If you want to set up a first date.
It’s 2019, and it’s absolutely fine for you to set up a date. It’s even fine if he is the one who asked you out, but you’re the one working on solidifying plans. It shows you’re interested, independent, and want the date to happen, which are all positive.

DO: If you just saw him.
Let’s say you’ve exchanged numbers, but haven’t texted yet when you happen to run into him at the gym when you’re wearing the cutest dang leggings. Let’s say you exchange some witty, sexy repartee and then he’s got to book it to hang out with his bros. Text him once he leaves or a little while after. A cute, “It was nice seeing you!” or something like that keeps up the emotional momentum that you guys already built and will hopefully move things into date territory.

DO: If you haven’t heard from him in a couple of days.
It’s not as common for guys today to follow strict “don’t contact her for X number of days” rules, but things happen. He might be busy at work or dealing with a personal issue. If you haven’t heard from him in a couple of days, send a  text like, “Hope you’re having a good day,” or if you have a date coming up, “Looking forward to Friday!” It shows you’re still interested, but not overeager or pushy.

DON’T: If you’ve sent more than three unanswered texts over a period of time.
Nothing turns someone else off as much as the overeager texter—the texter who shoots off three texts at a time and doesn’t even wait for a reply. You don’t want to seem desperate, so play it cool. A good rule of thumb to follow is to only send one text at a time. But maybe you send a “good morning!” text once a day over three days and get no response. Don’t send a fourth one. You don’t want to be the only one putting energy into a relationship, so don’t be the one putting all the energy in before you even get started. You want someone to meet you halfway, so make sure to check that it’s that way from the beginning.

DON’T: If you don’t have something thoughtful to say.
You want to text him, but don’t really know what to say, so you send him a simple  “hey!” Sometimes keeping it vague is ok, but to be a good conversation starter, show your interest by being thoughtful with what you bring up. A “hey” every time is boring. Maybe you discussed a movie coming out the last time you talked and you saw a new trailer for it has been released. Sending the link to the trailer along with a, “Remember when we talked about this?” shows you’re thinking about him and care about what you talked about enough to remember it.

DON’T: If you set up the last date, and now it’s his turn to set up the second one.
Some guys aren’t clear. They’ll say, “That was great! Let’s go out again!” And thennnnn you never hear from them again. Let’s say you set up the first date, and he’s told you, “Hey, I’d love to go out again.” You hopefully said something like, “I’d like that! Just text me to set up plans.” Now that you’ve set that scene, don’t text him first. If he’s interested, he’ll set up the next date. If he’s not, you’ll know quickly and can move onto the next cute guy. Again, you want to make sure that the energy you’re putting in is equal.

Dating is complicated enough. Texting shouldn’t be too! Following these rules can keep yourself sane and make sure whatever new relationship you’re about to start is a positive one.

Tara Mae Mulroy

Tara Mae Mulroy is a freelance writer and blogger who focuses on relationships. She is a regular contributor on Medium as well as the author of the full-length poetry collection, Swallow, and other writing found at taramaemulroy.com.

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