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When it comes to text messages, it’s horrifyingly easy to send your man the wrong message—literally and figuratively. And considering texting has only been around for a decade or so, the art of the perfect SMS has yet to be mastered.

And while you probably know that important conversations—whether you’re pissed at him or ready to talk about your future—should never happen via text, there are other iMessages you should never send his way.

1. “Looking forward to more nights with you like that.”
Alluding to a shared future—however benign your comment may seem—is a serious no-no at the start of a new relationship, says Laurie Davis, founder of eFlirtexpert.com and author of Love at First Click. [Tweet this tip!] Sometimes women get ahead of themselves and build up elaborate fantasies involving a future with their new man, but guys usually aren’t so quick to move that way, she explains. And any hints of serious commitment could frighten him—or anyone: Wouldn’t you be wary if a guy sent you this text after date No. 1?
Send this instead: “Last night was fun. Next time, my place?” Focus only on the coming date, and not beyond it, Davis advises. And avoid being too specific—like suggesting dates or times—which can make him feel boxed in.

2. “Want to meet my parents this weekend?”
For a man, meeting a woman’s mom and dad is fraught with all sorts of awkward possibilities, especially in the early stages of your courtship, explains Guy Blews, author of Realistic Relationships. Not only does this message scream, “I’m really serious about you!”, there’s really no way for the guy to say no without starting a fight, Blews adds.
Send this instead: “My parents are in town Saturday, so I may not be able to hang out.” If he shows any interest in their visit, you could mention that he’s welcome to join the three of you for dinner, but leave it at that, Blews recommends. “If he values you, he will be keen to make a good impression on your parents, and that's the guy you want them to meet.”

3. “Where have you been?”
“Two words,” Blews says. “Guilt. Trip.” Guilting a guy into anything is the best way to get used and abused, because you’re telling him you’re desperate, he adds.
Send this instead: “Hey, how are you?” If he likes you, that's enough to get him to reach back out, Blews says. If he doesn't reply, then you can send this exact same text a few days later, but only once more. If you still don’t hear from him, let go and move on.

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4. “We should be Facebook friends.”
Davis says this pops up most often with younger women. You probably just want to show your girlfriends pictures of the new guy in your life, but you feel awkward about friending him. The problem? Some guys might interpret this as "She wants to change her status to 'in a relationship' with me," Davis explains.
Send this instead: Take a screenshot of your Facebook page and send it to him with the message, “I’ll show you mine if you show me yours,” Davis suggests. It's flirtier and seems less like some sort of proposal.

5. “What are you up to?” (Sent anytime after midnight)
Unless you’re angling for a one-night stand as opposed to a real relationship, this message sends all the wrong signals to your guy. You might as well text, “Want to have sex?” because they’re basically the same message, Blew says. [Tweet this tip!]
Send this instead: “I’m wearing something I think you're gonna enjoy.” Send this well before 12, and you’ll leave him wanting more without him assuming you’re lonely, horny, tipsy—or all three, Blews says.

6. “Thinking of you.”
This could work with your boyfriend of multiple years, but send this to a guy you only recently started dating, and you may not realize you’re delivering a digital billboard that says you’re really, really into him—which could frighten him off, Davis warns. From a guy’s perspective, 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. Tell him you’re into him—and loved the date—without giving the impression that you’ve already started planning your wedding, Davis says. He doesn’t have to know that part!

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