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How’s Your Email Technique?


Find out right here—then read our advice on what you can do to make your messages even more eye-catching and intriguing than ever.

By Caitlin Ascolese

o you’re in like with someone’s profile. What’s next? Email, of course. Sure, it’s easy to treat this interim get-to-know-you stage lightly, but don’t be fooled: What you type can make or break whether you two hit it off. “Since it’s all they have to go on, people are constantly basing their view of you on how you email,” says dating coach Kathryn Lord, author of Looking for Action? “Your email style shows them what kind of approach you’ll take to a relationship.” Only what style emailer are you? Take this quiz to see what kind of impression your messages are making, then learn what you can do to improve.

1. How long are your emails to potential dates on average?
  1. Several paragraphs. You’ve gotta convey who you
    The best initial emails are short, flirty, and end with a question.
    are, and that’s not easy!
  2. A couple of short paragraphs.
  3. A couple of lines. No one wants to read a novel!
2. How many emails are usually exchanged before you suggest chatting on the phone or grabbing coffee?
  1. Ten or more—after all, email’s such a great way to get to know someone.
  2. Between five and ten.
  3. No more than two or three—no sense in becoming pen pals until you find out if there’s chemistry.
3. What sorts of questions do you usually ask in early emails?
  1. Big topics that really get to the heart of what a person’s like, like “What’s your relationship like with your parents?” and “What did you learn from your last breakup?”
  2. Light conversation, like “What was your favorite movie last year?” and “What’s the best place you’ve ever visited?”
  3. To-the-point basics, like “What neighborhood do you live in?” and “What’s your phone number?”
4. Your potential date asks you a question—like about what you do for a living. How do you reply?
  1. You tell them what you do, as well as the career path that brought you to this job and your goals for the future.
  2. With a sentence about your title plus an explanation of what that really means—and what you like about it.
  3. You state your position and your company. What more is there to say?
5. You get a “just saying hi” email recapping your cutie’s day and asking how you are. How long before you hit “reply”?
  1. Oh, about 30 seconds.
  2. A few hours, by the next morning at least.
  3. Whenever you finally have something interesting to say back.
6. You had an absolutely awful afternoon involving bad service at the coffee shop, dog poop, and a speeding ticket. When you’re writing to your e-amour that night, how do you share the story?
  1. You recount every second so he or she realizes how frustrating it was.
  2. A line or two detailing the nightmare.
  3. You just say you had a crappy day.
7. You get some photos forwarded to you of a pug in ridiculous outfits. The person you’ve started dating has a pug, too. You:
  1. Forward it along to your date as well as all your friends.
  2. Mention it laughingly in your next e-conversation and, if he or she wants to see it, pass it along.
  3. Delete the thing. So corny!


Answered mostly A’s? Then you’re an intense emailer
When you meet somebody new, you treat them like an old friend, from sending them forwards to long discourses on your day. But being so intimate so fast can backfire and make you seem overly familiar or needy. Your goal? To start paring down your emails (either in length or frequency) so that what’s left is pure quality.

To improve your initial emails...
Many online daters use email as a way to narrow down their options and will specifically search for red flags that’ll serve as a reason to weed you out. And given all the info you’re throwing at them, it merely ups the odds they’ll find something they don’t like (“Uh-oh, he made a Hillary joke, he’s out.”) So skip sharing your résumé and focus on simply intriguing
It shows the person you read his or her profile.
the person you’re interested in. “The best emails are two to three sentences, flirty, make a comment about something in the person’s profile, then end with a question about it,” says Liz Kelly, dating coach and author of SMART Man Hunting. “It shows the person you read his or her profile, and about 70 percent of these emails will get a response.”

For better letters later on...
The back-and-forth getting-to-know-you time is your time to shine, since you’re a natural at putting your personality into words. Just don’t let this phase go on for longer than a week or two—it’s a step in finding love, not the ultimate goal. And, as your email exchanges naturally become longer, don’t confuse your new pal with your online diary. OD’ing on mundane details or personal revelations is never appropriate, especially if you’ve never met the person. “Stick to socially accepted norms when it comes to topics—never say something that could scare a new friend off, even if this person will learn it later,” Alyssa Wodtke, author of Truth, Lies, and Online Dating. She also recommends making your emails a similar length as your match’s. Writing much longer emails than your partner makes you seem too interested. Once the flirtation goes offline and you discover the person truly deserves your trust, you can finally open up all you want.

Answered mostly B’s? Then you’re a cyber-charmer
You’re a master of the digital missive and use online communication to show off your personality. Each sentence you send encourages a real dialogue in the hopes of building an offline connection. But even masters can learn more.

To improve your initial emails...
You already know the secret to a good introductory email: A friendly sentence about why you liked the person’s profile plus a comment or question about it. If you want to make your emails even more irresistible, “You can start differentiating yourself right in the subject line,” says Evan Marc Katz, author of Why You’re Still Single. Most people settle for “hi,” but an intriguing subject line like “I’ve got an even better idea for how to…” will make a reader click on yours to find out what in his or her profile you’re referencing.

For better letters later on...
Your emails are already personal and friendly, but to up the intimacy, make sure to use the other person’s name — ideally once in the opener and, if it goes on for a few paragraphs, once near the end — to build rapport. You can also upgrade your emails by adding a touch of formality. “Since emails fly back and forth at lightning speed, they’re not always carefully read,” says Samara O’Shea, author of For the Love of Letters. “One way to set messages apart is by formatting them like actual letters. Start off with ‘dear’ and write a real note, rather than shorthand notes.”

Answered mostly C’s? Then you’re a casual correspondent
You prefer to live your life — not type it — so you use email to make simple introductions and plans. But those no-frills emails are the only thing that prospective dates have to judge you on, so being too brusque can be off-putting.

To improve your initial emails...
Sure, it seems obvious that you’re interested, so it just takes a quick line so the person will read your profile, right? Not so fast. “How a person communicates online tells you what kind of approach her or she will have to a relationship, and being too pointed can make someone think you’re uninterested or lazy,” says Lord. “To get a response, you need to put something meaty out there about why you’re interested.” You don’t have to slave over your life story—just give the person a sincere compliment that explains why you’re emailing, so he or she doesn’t think you’ve sent the same “hello” to everyone in a three-state radius. Good emails reveal something about yourself and why you’re into the person. If it sounds like it could have been written for anyone, delete it and start over.

For better letters later on...
Spend time on each email you send. It’s a commitment, but it’s what you signed up for. “Cool. Are you free Friday?” is not an acceptable response to a three-paragraph email about someone’s feelings. This simple formula can make emailing less onerous for you: In each email, make sure you comment on one thing the person told you about (so he or she knows you were reading), share something interesting about your own life (to build an actual connection), and then ask a question (so the person knows you want a response). After about a week of this plan, you’ve got the green light to answer the next question with, “There’s so much I could say on that but trust me, it’s more interesting in person. Want to chat about it over coffee?”


Caitlin Ascolese is a freelance writer in New York City.
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