Read This Before You Hit Send

Online daters, take note: Here are five mistakes you want to avoid when emailing — and why.

By Kimberly Dawn Neumann

ou winked and got winked at in return. Oh joy! Now what? Time to engage in e-conversation. Yup, one of you has to bite the bullet and launch that first email into cyberspace. But before you dash off a casual hello, make sure you think before you hit send. One little mistake and you could find your potential love interest running before hitting reply. “It’s so important to make the right impression in those first emails because, remember, this is like a blind date in cyberspace—and if you blow it in the first 200 words, you may never get another chance,” says Joel Block, Ph.D., a practicing psychotherapist. “Little things can make the difference between a ‘Hi, thanks for writing’ response and having nothing but crickets in your inbox.” In other words, don’t delay! It’s definitely worth the risk to reach out to someone. Just make sure you check for these five things first!

1. Please, please, please spell-check
“Hi. Thanks for righting. You seam grate.” Okay, we know that might be a little
Lots of people struggle with correct grammar and spelling…
extreme, but you’d be surprised with the number of poorly spelled, comma-happy emails people send. “If you can’t click a simple button to check your spelling, that makes a bad first impression,” says Amy Botwinick, founder of “It’s like showing up on a first date completely disheveled.” Lots of people struggle with correct grammar and spelling, but with the technology out there, not proofing your work — especially if you know this is an issue for you — is just, well… careless. Plus, it looks like you don’t care. “But there is no grammar-check button on my ‘compose mail’ function,” you say? Easily fixed: Copy your email, put it in a word processing document, run a spell/grammar check and voila. It’s not hard to ensure you’re making the right impression.

2. Make sure it’s not all me, me, me
Your profile? It’s all about you. That’s your calling card to the online dating community. And granted, while you probably won’t want to give away all your secrets in the “About me and who I’m looking for… ” section, you’ve hopefully posted enough to intrigue potential dates. Therefore, while it’s perfectly acceptable to add a little more info about yourself in an initial email to someone (or even the first few emails—this is a getting-to-know-you process), just make sure you remember to also show interest in the person you’re writing! “Pick up on something in the other person’s profile or note and respond empathically,” says Dr. Block. “Someone who comes off as ‘all about me’ is a definite turn-off. Practically everyone wants someone who is interested in them, rather than just being a prop for a ‘That’s nice, but let’s get back to me!’ response.”

How is this done? Ask questions about something in the person’s profile. Perhaps mention one of the photos that attracted your attention. Comment on any similarities or interests you both share. And don’t be afraid to throw in a compliment or two, because leaving an email recipient genuinely feeling good is never a bad thing.

3. Watch your mouth
When you launch your email offensive, double-check to make sure you haven’t said anything, well… offensive! This includes blatant comments about religion, race,
Addressing someone incorrectly can kill the mood.
politics, etc. “Attempts at online humor can also be dangerous early on,” says dating coach David Wygant. “If you’re going to poke fun or tell a joke, use a smiley face after so the recipient knows that this was an attempt at being funny.” Even with an emoticon as a qualifier, however, you would probably be smart to wait to push the comedy envelope too far until you know each other a little better. What one person finds hilarious, another may respond to negatively. As you strive for clarity in your writing, sense of humor often gets lost in cyber-translation. If you want make someone laugh, relay a funny story of something that happened to you and how you handled it, but save the edgier stuff for one-on-one conversations.

4. Learn to share with care
Don’t have an online identity crisis by giving away too much about yourself immediately. Feel free to include some details beyond what’s in your profile about your life, but use caution until you feel like you know and can trust the person with whom you’re emailing. “Too many people are chatting online with a false sense of security, which leads to inadvertently revealing too much,” says Botwinick. “Remember, what you reveal may provide more information than you realize—with just a few clicks on a search engine someone may find out where you live and where you work.”

So go ahead and talk about how many siblings you have, where you grew up, even what part of the city or county you live in, but you probably don’t need to offer up your full name, your birthplace or street address until you’re well into an online relationship that’s moving off-line for coffee (and even then, be prudent). This isn’t to scare you. We live in a day and age where it’s really easy to do some online sleuthing.

5. Double-check the recipient
“Dear Jo, How is your cat? Hope you had a nice weekend in New Jersey.”

Short and sweet. Except what if the recipient’s name is actually Jen, she owns a dog and stayed home for the weekend? One of the hazards of communicating with more than one person online, especially if you have a slew of e-conversations going simultaneously, is that you sometimes get a little confused. While we don’t recommend corresponding with more than a few people at one time (otherwise you’re probably not being discriminating enough), if you don’t pay attention, it can be dreadfully easy to slip up. So before you let the cat (or dog) out of the bag that you’re carrying on multiple conversations, double-check any emails you send for factual accuracy. Addressing someone incorrectly can kill the mood faster than you can type “Email me!” A little attention to detail can go a long way in making the right kind of online exchange. Now, go forth and initiate contact!

Kimberly Dawn Neumann is a dating/relationship writer based in New York City. Her work has appeared frequently online as well as in such publications as Cosmopolitan, Redbook, Marie Claire, Maxim and more. Check out her book, The Real Reasons Men Commit: Why He Will — or Won’t — Love, Honor and Marry You. You can find her at
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