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To text or not to text, that is the question. Find out how to decide whether or not to message a potential ~love~ interest and what not to say if you do.

By Markham Heid
Updated September 30, 2020
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If you've ever entered the dating scene, you've probably asked yourself the question, "should I text him (or her! or them!)?" at least once. Life would be easier if figuring out how long to wait to text a guy — or any romantic interest, for that matter — wasn't always such a mind game.

While there's no official rule book, there are a few general pointers you can consider the next time you ask yourself, "do I text him?" If you're newly dating, you might want to keep texting to a minimum, suggests to Jennifer Wexler, dating and relationship coach and founder of Find Real Love After 40. At that point, "texting should be used only to confirm logistics or if you're running late, not as your main form of communication," says Wexler. "Once you've been on several dates, text messages can also be a fun and flirty way to let your date know that you're thinking about them."

Even if you've decided you want to shoot this potential partner a text, you then have a bigger question to answer: "what should I message him?" When it comes to text messages, it's easy to get caught up wondering whether you're sending the wrong message — literally and figuratively. Considering how long texting has been around (#TBT to T-9 word), it's still surprisingly difficult to decide on the right tone and frequency. (Nevermind the appropriate use, if at all, of emojis.)

After a first date, Wexler recommends sending a text to thank them and/or show appreciation for something they did. And if you don't see things progressing, she suggests letting them know with a message that says something along the lines of "I'm glad we had the chance to meet but going forward I don't think we're a good match. I wish you the best."

If you're already a few dates in and find yourself staring at your blue light-lit screen wondering, "should I text him?" heed Wexler's advice: go ahead and send text messages (sparingly!) to let the person know that you're thinking of them, she says. "Avoid statements such as, 'Hey, how's your day?' Instead, be specific, i.e. 'Hey, just read this great article about the Lakers and it made me think of you.'"

And while you likely know that important conversations — whether you're pissed at them or ready to talk about your future — should never happen via text, you might be surprised to find out that there are other messages that you probably shouldn't send in a new relationship as well.

1. "Looking forward to more nights with you like that."

Alluding to a shared future — however benign your comment may seem — can be startling at the start of a new relationship, says Laurie Davis, author of Love at First Click. Women are quicker to build up elaborate fantasies involving a future than men, she says. And any hints of serious commitment could frighten them. And the same is likely true for you — after all, wouldn't you be skeptical if someone sent you this text after the first date?

Send this instead: "Last night was fun. Next time, my place?" Focus only on the coming date, and not beyond it, advises Davis. And avoid being too specific — such as suggesting dates or times — which can make someone feel boxed in. (If you want to take the next step, here's how to go from a casual to a committed relationship.)

2. "Want to meet my parents this weekend?"

Meeting someone's mom and dad is fraught with all sorts of awkward possibilities, especially in the early stages of your relationship, explains Guy Blews, author of Realistic Relationships. Not only does sending this text scream, "I'm really serious about you!" but there's also really no way for them to say no without starting a fight, adds Blews.

Send this instead: "My parents are in town Saturday, so I may not be able to hang out." If he or she shows any interest in their visit, you could mention that they are welcome to join the three of you for dinner, but leave it at that, recommends Blews. "If they value you, they'll be keen to make a good impression on your parents, and that's the person you want them to meet."

3. "Where have you been?"

"Two words," says Blews. "Guilt. Trip." Sending a text such as this — or guilting them into anything — can (and likely will) backfire because it can come off as desperate, he explains. (Ugh. Suddenly answering the question, "should I text him?" seems like a walk in the park.)

Send this instead: "Hey, how are you?" If they like you, that's enough to get them to reach back out, explains Blews. If they don't reply, then you can send this exact same text a few days later — but only once more, he says. If you still don't hear from them, let go and move on. (Related: How to Travel with Your Significant Other Without Breaking Up By the End of the Trip)

4. "What are you up to?" (Sent anytime after midnight)

If you're looking for a one night stand or FWB situation, then this one's fine. But if you're interested in a relationship, you shouldn't shoot off this text willy-nilly because it can send all the wrong signals. You might as well just text, "Want to have sex?" because it's basically the same message, says Blews. (And if you do just want sex? Go ahead; hit send and get after it. Or, you can always take matters into your own hands — literally — with a mind-blowing masturbation sesh.)

Send this instead: "I'm wearing something I think you're gonna enjoy." Shoot this bad boy off well before 12, and you'll leave them wanting more, explains Blews.

5. "Thinking of you."

This could work with your partner of multiple years, but should you text him this right away? Then you're basically delivering a digital billboard that says you're really, really into them, which could frighten them off, warns Davis. Simply put: This could be too much, too soon.

Send this instead: "Had a great time with you. Let's do it again soon." Before you get serious with someone, dating should be fun. Show you're interested — and loved the date — without giving the impression that you've already started planning your wedding, says Davis. Even if you're already scouting bridesmaid dresses.

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