You know your way around a computer keyboard, and you’re all set to use it to charm an army of potential love interests. From the initial introduction to heartfelt conversations down the line, you know the unwritten rules: be nice, make it personal, use spell-check. Still, even the very best emailers make certain mistakes. Read below for a list of no-nos that might surprise you — and for the easy ways to fix them, according to experts.

Embarrassing mistake #1: Getting personal… as in, too personal
It’s so easy to feel comfortable when you’re online — you’re safe behind a glowing 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 circle friends, it’s even more natural to just start typing about big issues whenever the topic comes up... but that’s not always healthy. “Online messages 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?”

Solution: 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 short, 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.”
View Singles on
Embarrassing mistake #2: Using super-common (and immature-sounding) shortcuts, such as emoticons and Internet slang
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 Find a Sweetheart Soon. Overloading on emoticons and acronyms (LOL, OMG, IMHO) says that you’re squeezing time for dating into your busy schedule, not truly spending time on each interaction in a thoughtful, respectful manner.

Solution: 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 as though he or she genuinely understands how you think and feel. That’ll accelerate your real-life connection in a mature manner and set the tone for future communications if a relationship blooms between the two of you.

Embarrassing mistake #3: Prematurely responding to an email without thinking about what to say first
Most of us are so used to emailing and texting that it’s totally instinctive to just hit reply and send back our thoughts in an instant — but that can easily go wrong, especially in the getting-to-know you stages. “Emailing back too quickly gives your love interest the impression that you’re just sitting around, bored, and waiting for him or her to write,” says Alyssa Wodtke, author of Truth, Lies, and Online Dating. And even if you’re just a really fast typist, it also sends the message that you didn’t spend much time thinking about how you’d respond. Finally, 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 get back to him or her instantly, the person might wonder what’s wrong. Why get sidetracked by all that?

Solution: 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 email at a certain time of day sends the message that that’s when you handle your personal email.”

Embarrassing mistake #4: Accidentally insulting the other person because he or she misreads your tone
It’s unfortunate that email doesn’t come with a laugh track or sarcasm font. “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 an intentionally 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 an otherwise great match.

Solution: Using humor in your email messages is fine — in fact, it can set you apart and really highlight your personality. But the caveat here is, be smart about it. Reread any jokes aloud in a couple of different tones, and if there’s any chance he or she could take what you said the wrong way, make sure to over-explain that it’s just you expressing your particular sense of humor. Once your recipient gets to know you better, you won’t have to qualify your barbs with “Obviously I’m just joking — no sane person would think that!” Until then, it’s worth adding the disclaimer so you don’t accidentally put your foot in your mouth.

Embarrassing mistake #5: Stating the obvious in a bland message that gives the recipient no reason to write you back
Plenty of people send some version of this introductory email on various dating and social media sites: “Hey, I saw you online and 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 absolutely nothing about you or why this person should respond. Think about it: You obviously saw the person’s profile, tweets, photos or Facebook page and found something that piqued your interest or else you wouldn’t have written, you obviously like him or her and find this person attractive, and clearly, he or she is going to read your email, check out your online persona and then decide whether to write back. And hey, not to be blunt about this, but: everyone likes traveling and eating out. You could accomplish the same thing if you’d just written “Hi!” A similar offense is writing a shortened version of your life story in the first email — all the same info the person will get anyway when looking at your online presence. “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: Things Your Friends Would Tell You If You Promised Not to Get Mad. “What’s the point of doing what everyone else does?”

Solution: Instead of wasting empty words, write something that’s both tailored to the recipient and gives the person an extra hint of “you” that he or she won’t get anywhere else. Comment on something mentioned in the person’s bio, then give your own take or recommendation on that topic — and suddenly, you two have developed a rapport; you’re no longer just exchanging autobiographies.

Embarrassing mistake #6: Cutting and pasting your basic info into a form letter and then blasting it out to everyone
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, and whatever else it is you care about. 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 really 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, and 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 at all make it easy to spot a form letter. Men especially should be wary of doing this!

Solution: Instead of going into so much detail before you’ve even met the person, write 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, offers your potential date something to look forward to, and it spares you both from your eyes glazing over after being inundated with a bunch of background info you’re never going to remember, anyway.

Embarrassing mistake #7: Switching to a different mode of contact without discussing it together first
After a few nice exchanges over email, many people decide for convenience’s sake to start communicating using their personal IM or directly from their smartphone. That’s all well and good, but remember: when you fire off that first note, it doesn’t come with your picture attached. It’s also not a given that your love interest will instantly realize that is you when he or she gets your message, much less respond to a text or IM from an unfamiliar phone number. “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 nobody else, which often makes it feel awkward for both of you.”

Solution: This mistake couldn’t be easier to fix. “Just say: ‘Hey, it’s so-and-so from [site],’ then put your familiar username/contact method in the first thread of the conversation. That way there’s no confusion,” advises Griffen.

Embarrassing mistake #8: Off-putting background templates, embedded graphics, or sign-off lines that are automatically added to your messages
It sounds totally petty, but 10 years ago, people listened to every voicemail over and over trying to gauge hidden meanings, and today, email is really no different. Don’t believe us? Consider how formal and weird a “Kind regards” or “Best” sign-off just above your name can sound after reading a heartfelt getting-to-know-you paragraph, or how presumptuous a typed-without-thinking “Love” or “XOXO” reads to someone who barely knows you. And don’t even get us started on how a goofy background image, link to your Kickstarter campaign or embedded weight-loss goal tracker can make your recipient worry that you’re emotionally stunted.

Solution: Try signing off with something that’s both simple and impossible to dissect, like: “Sincerely,” “Have a great day,” or the especially confident “Talk to you soon.” “A sincere sign-off 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.

Caitlin Ascolese is a freelance writer in New York City.