Oops! Your Top Email Mistakes—Solved

Sure, you spell-check and include a compliment…still, could your messages contain some unseen turnoff? Here, eight to avoid—and what to do instead.

By Caitlin Ascolese

ou know your way around a computer keyboard, and you’re all set to use it to charm an army of potential matches. From the initial introduction to heartfelt convos down the line, you know the unwritten rules: Be nice, make it personal, spell-check. Still, even the very best emailers make certain mistakes. Read below for a list of no-no’s that might surprise you — and for the easy ways to improve.

E-tiquette mistake #1: Getting personal… too personal
It’s so easy to feel comfortable online—you’re safe behind a computer screen and only know the best things about the person you’re chatting with. And if you use IM and email to share your everyday dramas with your pals, it’s even more natural to just start typing
Peppering your emails with “L8R” and “LOL” is not a good idea.
about big issues when the topic comes up. But that’s not always healthy. “Emails that offer too much information about your life story can be a big turn-off,” says dating coach Liz. H. Kelly, author of SMART Man Hunting. It creates a false sense of intimacy, puts more pressure on both of you to actually live up to the secret-sharing status you’re on, and sets the stage for awkward in-person conversations (instead of asking about your last relationship when the topic naturally comes up, all that’s left to ask is, “So, did your ex ever come by and pick up those boxes you’d said you were thinking about burning?”).

Instead, try this: Ask yourself, “Would I be comfortable sharing this detail with the new guy at work/someone I was having coffee with for the first time?” That’s approximately how well you know the person you’re emailing. If the thought makes you cringe, cut it altogether or, if you’re answering a question, give the sort of answer you’d use on a job interview. “If someone asks you, say, about your divorce, give them a one-line, highly general response,” says Kelly. “There’s no need to share your deep, personal thoughts until you’ve had a few dates and have actually built up trust.”

E-tiquette mistake #2: Super-common shortcuts
Don’t assume that your fluency in online jargon will translate when it comes to romancing someone. “Emoticons and language shortcuts are risky, because they look affected and a lot of people really hate them,” says dating coach Kathryn Lord, author of Looking for Action? Overloading on emoticons and acronyms (LOL, TTFN, IMHO) says that you’re squeezing courtship into your busy schedule, not truly spending time on each interaction.

Instead, try this: Take the time to spell out words, and instead of plugging in a smiley (or sad or winky) face, make that your cue to write a sentence about how you’re actually feeling. Crazy stuff, we know—but doing this will make your recipient feel not only respected, but like he or she knows more about how you think. That’ll accelerate your real-life connection… OMG!

E-tiquette mistake #3: Prematurely responding
Most of us are so used to emailing that it’s totally instinctive to just hit reply and send back our thoughts. But that can go wrong in the getting-to-know you stages. “Emailing back too quickly gives a person the impression that you’re just sitting around waiting for him or her to write,” says Alyssa Wodtke, author of Truth, Lies, and Online Dating. And even if you’re just a fast typist, it also sends the message that you didn’t spend much time thinking about a reply. Lastly, it creates a pattern where the person always expects you to write back ASAP, so if you happen to be busy one day and don’t, he or she wonders “What’s wrong?” Argh!

Instead, try this: If you’re so excited to respond that you can’t stop yourself from writing right away, at least save it as a draft and hit “send” later. “Note how quickly the other person responds and use that as your guide,” says Wodtke. “Writing back within a day or two is best, and doing your emails at a certain time of day sends the message that that’s when you handle your personal emails.”

E-tiquette mistake #4: Accidental insults
It’s unfortunate that email doesn’t come with a laugh track. “We forget that the receiver can’t hear our voice, read our body language, or know when we’re smiling,” says Bev Bacon, author of Meet Me… Don’t Delete Me! Internet Dating: I’ve Made All The Mistakes So You Don’t Have To! “We may write something jokingly, but it comes across as a slam.” That’s especially true when you’re using sarcasm or making a purposely bad pun. You may think it’s obvious that you’re being facetious when you say something like “Clearly, all the single women in this city are bonkers,” but in a world where everyone’s on guard for potential red flags, you may just hit a nerve and turn off someone who’d be a great match.

Instead, try this: Using humor in your emails is fine—in fact, it can set you apart and really highlight your personality. But be smart about it. Re-read any jokes in a couple of different tones and if there’s any chance the person could take it the wrong way, make sure to over-explain that it’s just your sense of humor. Once your recipient gets to know you, you won’t have to qualify your barbs with “Obviously I’m just joking—no sane person would think that!” but until then, it’s worth the disclaimer.

E-tiquette mistake #5: Stating the obvious
Plenty of people send some version of this introductory email: “Hey, I saw your profile, I think you seem cool. I enjoy traveling and eating out. Check out my profile and write me back if you can!” Sounds sweet, right? Too bad it says nothing. Think about it: You obviously saw the person’s profile or you couldn’t have written, you obviously like him or her or you wouldn’t have written, and clearly he or she is going to read your profile and
The point of email is to capture someone’s attention.
decide whether to write back. And also, everyone likes traveling and eating out. You could accomplish the same thing if you’d just written “Hi!” A similar offense is writing everything about yourself in the first email—all the same info the person will get anyway when they look at your profile. “The point of email is to capture someone’s attention and differentiate yourself,” says dating coach Evan Marc Katz, author of Why You’re Still Single. “What’s the point of doing what everyone else does?”

Instead, try this: Instead of wasting words, write something that’s both tailored to the recipient and gives them an extra hit of “you” that they won’t get from your profile. Comment on something they mentioned in their bio, then give your own take or recommendation on that topic—suddenly you two have a rapport, not just alternating autobiographies.

E-tiquette mistake #6: Cutting and pasting basics
Sure, there are topics that you’re probably going to keep covering in your email correspondence from person to person: where you live, your favorite bands, whatever. So lots of people whip up a standard set of paragraphs, then cut and paste them into all the emails they send… but according to experts, this is a bad idea. “It takes away from the natural way the conversation should go, and people definitely know,” says Roman Griffen, author of Internet Dating: Tips, Tricks, Tactics. A sudden change in tone or tense, a different font or margin, repeating details that you two have already covered or offering what sound like scripted answers to a question that hasn’t been asked all make it easy to spot a form letter.

Instead, try this: Instead of going into so much detail before you’ve even met the person, give a sentence or two in your own fun voice and say “I’ve got plenty of stories on that subject—remind me when we have coffee to tell you about the time such-and-such happened.” That gives your fingers a break, gives your potential match something to look forward to, and spares you both from glazing over a bunch of background info you’re never going to remember anyway.

E-tiquette mistake #7: Not saying “hello”
After a few nice exchanges over’s double-blind email system, many people decide for convenience’s sake to start communicating using their personal email address or IM. That’s all well and good, but remember: When you fire off that first note, it doesn’t come with your picture and profile attached. It’s also not a given that your cyber crush will instantly realize that is SanFranGolfer when your email arrives. “If you don’t identify yourself, the person may have no idea who you are,” says Griffen. “It’s naïve to think that people are only exchanging emails with you, and it makes it awkward for both of you.”

Instead, try this: This mistake couldn’t be easier to fix. “Just say ‘Hey, it’s so-and-so from,’ and put your username in one thread of the conversation, and there’s no confusion,” says Griffen.

E-tiquette mistake #8: Off-putting signoffs
OK, it sounds totally petty, but ten years ago, people listened to every voice mail over and over trying to gauge hidden meanings, and today email is no different. Don’t believe us? Consider how formal and weird a “Kind regards,” or “Best,” can sound after a getting-to-know you paragraph, or how presumptuous a typed-without-thinking “Love,” or “XOXO” is. And don’t even get us started on how a goofy “L8r sk8r,” “C ya!” or “Payce,” can make your emailee worry that you’re emotionally 14.

Instead, try this: Try something simple and impossible to dissect, like “Sincerely,” “Have a great day,” or the confident “Talk to you soon.” “A sincere signoff with your name, not just your initial, calls attention to the fact that your message was written thoughtfully, not in a hurry,” says Samara O’Shea, author of For the Love of Letters: A 21st Century Guide to the Art of Letter Writing, from the Elegant to the Erotic.

Caitlin Ascolese is a freelance writer in New York City.
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