CHAPTER 4
Email Education

FLIRTING THROUGH INBOXES

Winking is dead. No, not the real-life eye fluttering, but the button you’ll find next to someone’s profile that allows you to show interest in a match. Some sites call it Smiling or Flirting, but regardless it serves the same purpose: to let you gauge interest in someone before investing hours poring over every period of a single clever email sent to their inbox.

Years ago, when dating sites first entered the scene, Winking was all the rage. But it has become an increasingly passive action. Consider this: if a Facebook “friend” you’ve never met face-to-face “liked” your status update, would it inspire you to write a detailed email in return? I think not. Needless to say, your first interaction with a clickable mate is often your make-or-break moment and should not come by way of a generic emoticon. It’s unlikely that it will inspire any action . . . in your inbox or otherwise.

The truth is that women can sometimes still get away with merely clicking the Wink button—especially hotties with bodies. But if you’re truly interested in a match, you shouldn’t blow your one opportunity with a seemingly meaningless attempt. Isn’t your future partner worth a few sentences?!

Of course, the most important reason to ignore Winking online and leave it only to real-life scenarios is “mat-uration,” the saturation of matches like you on a site. The number of singles dating online is growing every day, which means that more and more conversation is happening. You want to make sure that you’re an active participant so you don’t get lost in the shuffle and miss an opportunity with a match simply because his or her inbox is flooded and Winks are automatically deleted. (Trust me, singles do it.) In fact, many eDaters are even savvy enough to spot a generic, template message and get rid of them without so much as a response.

To be truly proactive and productive in your digital dating life, you have to click Compose and start typing a message tailored specifically for your cyber-crush’s eyes only. There are four phases of sending messages: first messages, email replies, transitioning offline, and following up. But each needs to be approached differently; let’s break it down.
First Emails

Sending a first-email flirtation has three purposes:

1. Get a match’s attention. Technology should always work for you, not against you. But the truth is that with so many potential matches online, it’s possible that Mr. or Ms. Right (or Right Now) might not come across your profile. Maybe your profile doesn’t make a cameo until page 10 of their search results. If they sign off after viewing only five pages, they’ll miss you entirely. What you’re saying at the most basic level when you send an email is “I exist, listen up!”

2. Qualify yourself. Vouching for yourself as a qualified match is important. So even though you’ve already created a profile, you want to rehash what makes you a clickable mate for them. Avoid pleas (“If you like what you saw on my profile, too, message me back”) and basics (“I’m a well-educated, charming, and funny guy looking for a woman like you”), and qualify yourself more naturally by mentioning an interest or two that you share.

3. Start a conversation. Remember that messaging takes two—if you don’t begin chatting, you’ll never get offline. Encourage conversation and responses by writing an email meant specifically for him or her, and then ask a question. Questions show that you have genuine interest in getting to know someone and really begin the conversation.

Applying all three of these criteria creates email perfection. But deciding what to write once you click Compose isn’t always as clear-cut or straightforward.

Getting responses to the emails you send starts with reading your match’s profile.

Just as you may experience love at first sight in person, a similar tug at your heartstrings could happen when viewing a match’s pictures. But just because someone’s photos are swoon-worthy doesn’t mean you should skip the rest of their profile—you might be missing out on some vital information (or even a red flag or two). You’ll also get to know specifics about your common interests that you can talk or ask more about, showing this digital cutie that yes, you cared enough to read through the profile, making it more likely that you’ll get a response.

But there will also be cases when someone just seems right for you, even though you can’t put your fingertip on what makes that person your “type.” It might be his or her sense of style, the tone of the About section, or simply one funny sentence that literally made you LOL. And that’s when crafting an email that qualifies yourself and starts a conversation can clinch permanent space on his or her heart’s hard drive.

If it’s not immediately apparent how you’ll click, ask yourself: What do I like about him or her? This will help give your email direction. I do this exercise with Khristine during our weekly sessions. As a thirty-four-year-old New Yorker with a busy schedule, she meets with me to be held accountable for the time she commits to online dating and the decisions she makes. Her first thought about what appeals to her in someone’s profile is usually along the lines of “He seems genuine.” But after a few moments, she’ll come up with a few others, such as “He sounds successful like me,” or “I haven’t read that book he mentions yet, but I really enjoyed the author’s first novel.” And suddenly, we have a perfect topic for her first email. Discussing how genuine someone seems is too intangible and broad a topic for a first message. And while success is fantastic, we don’t want to start off a pending love connection with job talk—it’s not very romantic! However, discussing favorite authors not only highlights a similar interest but also shows comparable levels of intelligence, which is important if you pride yourself on book smarts as much as Khristine does.

If you’re having a hard time determining a topic for a message, look at passions and keywords.

Passions are the best topics of conversation, particularly if you have a few in common. Believe it or not, I notice that passions are not usually the focus of people’s profiles. But by looking closely at language and phrasing, you can figure out what a match is excited about in life. For example, if someone mentions an organization like Habitat for Humanity, you can bet that helping others is something he or she cares deeply about. If you can tap into what people have a passion for, they’ll want to respond. After all, when someone asks you about something you love, don’t you just want to gush all about it?

Reviewing keywords doesn’t require you to read between the lines the way finding a passion does, but it’s a solid strategy if you’re struggling to find a point of connection. Scan your match’s profile for interests that you share, such as travel, yoga, or family. If he or she doesn’t expand on the topic in their profile, use your message as an opportunity to ask more about it, while giving insight into why that topic ranks high in your life.

INTRODUCTION TO INTRODUCTIONS

Now that you’ve determined a topic, let’s dive into the components that make up a great email.

Greeting. Since the purpose of a message is to begin a conversation, skip traditional letter etiquette. “Hello,” “Yo,” “Hiya,” and other jargon create a more formal tone than you want to project. Hands down, the best way to begin an email is just to jump right in with no salutation at all. While it may seem strange, it creates instant familiarity, which will encourage him or her to feel a connection. I’ve always seen the best results with my clients who follow this advice, and OkCupid agrees: avoiding a salutation gets the highest response rates on that site. But if skipping a salutation feels too strange to you, note that OkCupid found that “How’s it going?” “What’s up?” and “Howdy” ranked high as greetings in its study.

Content. As you did with your profile, skip sentences that sound generic. Being specific is even more important in messages, because you want to show honest intent. If the message sounds even a little bit as if it wasn’t written specifically for the recipient, you risk missing out on a reply. Ideally, you should stick to one topic so your message is focused. If there are two that go hand-in-hand, you can expand, but more than that, and you risk sounding too interested for a simple hello.

eFlirt Byte: According to OkCupid’s email study, every niche word or phrase the site has data on has a positive effect on messaging, such as “vegetarian,” “band,” and “grad school.” And phrases that engage these interests and show that you’ve read the other person’s profile are also likely to get responses, like “Curious what . . . ” and “Noticed that . . . ”

Language. However, remember that this isn’t a text message, either; you should still use proper grammar and sentence structure. Steer clear of netspeak like “ur,” “ya,” or “wat.” Because OkCupid is a free site, I’d expect some of its members to be the most forgiving of this digital behavior, but the site’s study found it to be a strong deal breaker. However, users do respond well to humor, so “haha” and “lol” are OK.

Question. Asking one question at the end of a message is a must. While profile “calls to action” are subtle, those in emails should be more direct. The easier you can make it for the recipient to respond, the more likely you are to get a reply. But it’s just as important to make your call to action clear. Asking three questions instead of one can become overwhelming or feel like badgering, and the person might not respond at all. And keep the question simple. Elaborate inquiries require your match to give serious thought to responding and, again, can leave you with no response. Start with your experience on the topic, and then ask a simple yes-or-no question. Uncomplicated questions will encourage your match to expand on the topic.

Subject. Most dating sites allow you to create a title for your message, which is what your match will click on in his or her inbox. Make sure it is click-worthy, and avoid generic lines like “What’s Up?” or “Let’s Talk.” You want the title to speak to the topic so your match knows what they’re clicking on. But remember that this is your dating life, not corporate life. Skip titles that are dry, such as “Cooking,” and instead use something with personality, like “Battle of the Lasagnas.” When your match’s inbox is bursting with messages, yours will be much more likely to stand out.

Signature. Always close the email with your name. While this might sound like a no-brainer, many singles leave it off and risk coming across as mysterious—and not in a good way. Sending a match a message means that you’re introducing yourself, so make sure you do that. Plus, signing with your name instantly warms up the tone of the email. Needless to say, you should also skip any extraneous information, like a full signature with your title, email address, and phone number. Not only does this set too formal of a vibe, but it also compromises your safety.

Let’s put these principles into practice. Ultimately, an email should look similar to the following:

From: sunnysideup

Sent: January 22 8:43 PM

To: DownWith311

Subject: Poker Face

I’m a budding poker player, too. Right now, I’m reading Small Stakes Hold’em to brush up on my game. In March, I’m heading to Vegas, but quick trips to Atlantic City with friends are fun, too. Where do you play?

Sarah

A first message should be short and sweet; there’s no need to bare your soul before your match even says hi. Ideal length depends on gender, location, and age. Women should write less, usually three or four sentences—much longer, and you risk appearing overenthusiastic. Traditional gender roles dictate that men should be the aggressors, so when you do the approaching, give the guy some space to take the reins later. Men should write a bit more, but still not too much—four to ten sentences is ideal. This will show that a decent amount of time and thought went into the email. But also keep geography in mind; younger or urban singles like Sarah favor shorter messages, while more mature or suburban/rural singles often have more traditional values and want to know that you put significant effort into contacting them.

Template emails are the pickup lines of the Web.

Being proactive and sending an appropriate number of emails is important, but avoid copy-and-paste jobs—you know, template messages that are so generic you can send them to matches in bulk. They’re the “How do you do’s” that aren’t tailored to a match and often rub people the wrong way. Approaching a cutie in real life with a cheesy line will either result in an eye roll or attract a lower-quality mate, and the same is true of the Wink Wide Web.

The first time I logged into Jonathan’s inbox to assess his emails, I had to step away for some deep, cleansing breathes. He had sent everyone in the continental U.S. with any potential the same template message:

Youre so gorgeous, I’d fly to [fill in the blank] to see you, call me 305-555-9823 xoxo Johno

Sending the same message to every match may seem efficient, but skimping on personalized messages is actually a major time waster. If your first email is the online equivalent of a first encounter, template emails are worse than a limp handshake. Jonathan’s emails epically failed, because he gave a disingenuous compliment (“gorgeous,” when he’d never met her before), was overenthusiastic (saying he’d jet over ASAP), made himself seem too available (revealing his phone number), and ended with faux affection (kisses, hugs, and a nickname).

Remember, a little email foreplay is never a bad thing. But that’s not what “Johno” was serving up. His messages screamed “You’re not worth getting to know more, so let’s just meet offline and be inappropriate together.”

The one circumstance when templates can sometimes be effective is when you’re only looking to date casually, because you can increase the number of messages sent. In these cases, emails are typically shorter, and the tone is more laid-back. Take Alex, my twenty-nine-year-old client whose preference was to schedule at least three dates a week and simply have fun and see what happened. In that case, I drew up outlines that he could use in place of templates. Of course, they still required him to do some work, but he could more easily increase his output. This is OK, because over time, there are common topics you find appealing in others’ profiles that you may use often to message matches. One of his big interests is travel, and most of the matches he chose had a large appetite for going abroad, too. So I created this guideline with travel as the focal point:

Looks like your travel bug is as big as mine. My favorite trip so far was the Amalfi Coast—the architecture was amazing. [Country] must have been—. I [have/haven’t] been there before, [and/but]—. I have a trip to Prague and Amsterdam planned this summer, which I’m really excited about. Where are you headed next?

Alex

When creating an outline, be sure to erase signs of it being generic by remaining hyper-focused on the topic. As much as possible, remove blanket sentences that sound as if they could be sent to anyone, such as “I really enjoyed your profile.”

And if you see the same match on more than one dating site, don’t message in two places. Reaching out twice becomes badgering. If the person wasn’t attracted to your profile from the start, there’s nothing about a duplicate message that will be a turn-on. Stay focused on writing messages for new people to keep the positivity flowing in your dating life.
Email Replies

Emailing is the digital equivalent of courtship.

When my clients are online dating newbies, sometimes their first instinct is to get offline and talk on the phone immediately. This was the case for Julie, who messaged with a match once and then dropped her number, requesting that he contact her that same evening between seven and ten. But her phone never rang.

Never mind that scheduling the call was too formal (and too short notice); making the transition from first email to the phone changes the method of communication drastically before you know each other, making it more likely that singles won’t follow through. And when you do this so soon, there is less incentive to call, because they still don’t know much about you.

It’s important to get comfortable with cyber chatter, because it’s part of courting someone in a 2.0 world. Skipping straight to the phone means you miss out on the natural development of a dynamic. As a result, phone calls and dates might seem forced, and connecting with someone when you’re offline can be more challenging.

But if you’re asked to chat voice-to-voice early on and you really like the person, go ahead and follow his or her lead if you’re comfortable with it. Even though it’s best to eCourt each other, you don’t want to block your eFlirting energy from moving forward—offline.

With Julie’s next match, she exchanged six emails before connecting offline. This time, not only did he call, but they ended up dating for a few weeks.

Gone are three-day rules; all hail real-time gratification.

Stop wasting time debating whether you should wait until tomorrow or Tuesday to write back to your match, and just hit Reply. This rule is in effect always and forever, whether you’re dealing with an ongoing email string or a new eFlirtation. Your goal should be to reply to a message within twenty-four hours. Do yourself a favor, and download your dating site’s mobile app to help keep you on point. Just be careful of typing errors, and always reread what you’ve written before pushing Send so you’re not a victim of auto-correct.

When you click Reply, your focus should be on remaining a good conversationalist. Just as when you’re chatting in person, you want to keep the flow going and the momentum moving in a getting-to-know-you direction. This means showing interest by asking one or two questions (it’s OK to ask more than one once you’re both engaged in chatter) and expanding on questions about yourself. But keep your responses to no longer than one paragraph per topic.

Here’s a message string between Kyle, a twenty-nine-year-old teacher in Boston, and his latest lady. Let’s see firsthand how a great relationship starts via email.

From: openpassport

Sent: January 7 5:28 PM

To: beachesandtoes

Subject: China Vacay

One of your photos reminded me of my trip to China. I went with a friend, and we explored Mt. Taishan, one of the Five Sacred Mountains— an eye-opening experience. The best dumplings I ever had were by a chef nicknamed “Elton John” in my friend’s rural village. What was your trip to Asia like?

Kyle

Hi Kyle,

Glad you liked my photo. The waterfall I photographed was actually at Mt. Taishan, too. I went to China about two years ago and had a fascinating time, though wasn’t lucky enough to run into Elton. ;)

I actually just got back from Chicago tonight—just in the nick of time, since snow seems to be looming. But what else is new! Maybe you’ll get a snow day tomorrow. What grade do you teach?

Tanya

Hey Tanya,

I just got in from a huge workout that I’m officially dubbing the Snow Shoveling Marathon.

Luckily I got the “no school” call last night. I teach fifth grade, which is interesting because the kids are at that age where they’re just starting to learn the definition of a crush.

I’m glad you made it out of Chicago before all the airports closed. Being stuck somewhere is right up there with breaking a bone on my continuum of life experiences. Tough time of year to be in Chicago—were you there for business or fun?

Kyle

Hey Kyle,

Fifth grade, how cool! For me, that was the prime note-passing age.

I was in Chicago for fun—actually, it was a girlfriend’s bachelorette party! The best part by far was our dinner at Wildfire. Best. Steak. Ever. Have you ever been there? Let me tell you, after the weekend we had, I’m on an official wine detox!

Tanya

Hey Tanya,

I haven’t been to Wildfire but will have to add it to my list of to-do’s next time I’m in Chi-town. Steakhouses are a favorite. I’d love to continue chatting offline—maybe we can make snow angels and then warm up with a hot chocolate. I hear whipped cream is the new detox. When are you free this week?

Kyle

Hey Kyle,

How fun! A hot chocolate and some snow-angel workouts sound exactly like what my system needs. ;) I’m free Saturday or Sunday afternoon. Let me know which works better!

Tanya

Hey Tanya,

Saturday is great. Let’s meet at 2 PM in front of Thinking Cup, and then we can head over to the Boston Common together. In case anything changes (and so we can find each other), my number is 781-555-2387. Looking forward to meeting you! :-)

Kyle

Awesome! See you then. My cell is 617-555-9831.

Tanya

Kyle is one of my success stories; he’s now in a relationship, and I couldn’t be prouder of his eFlirting skills. Every time a client like him emails telling me that he or she is seeing someone seriously, I blush from head to stiletto from the thanks—I can’t help feeling the love radiating off the computer screen.

Every email exchange is different, meaning that “rules” can’t truly exist; however, there are nuances that can be learned from Kyle and Tanya’s connection:

Hi, hello, hey. Kyle followed my advice on first messages to a T. His initial email not only reads well and is interesting, but clearly, it caught Tanya’s eye. When she responded, she said “Hi.” Good but not great. “Hi” is a little formal for flirting territory, but when Kyle followed up, he said “Hey.” And then she followed his lead. Small word choices like this will help create a more comfortable cyber-environment and help you get offline for a date.

Conversation versus content. Kyle successfully mixed new information about himself with casual conversation. He related well to her and showed interest by asking questions, but he also added enough details about his own life to keep the momentum moving. When one person drops off the email string, it’s usually because the right mix of both elements is missing. Remember: relate, then add.

One question per paragraph. You don’t want to overwhelm someone with questions, so stick to one per paragraph. This will to force you to include content alongside your inquiries.

Emoticons. In the first email Tanya sent, she Winked. This is always a good sign from a lady—digital flirtation at its finest. But Kyle waited until the last email to smile. In a male-female situation, this is the right approach. Although it may sound strange to advise men not to reciprocate a virtual smiley, emoticons typically give off energy that isn’t as confident—as if you have to justify your statement, even though the real purpose is to show excitement. Avoid them until the end of an online string, since that’s where you want to convey more genuine emotion and excitement; that way, it shows that your virtual Wink is the real deal.

Number-drop. Even if you’re not going to talk on the phone first, dropping your digits is important. It almost always encourages the other person to reciprocate. This way, if one person is running late or you’re in a crowded space and are having trouble recognizing each other, you can be in touch.

Creative date ideas. Planning a date beyond cocktails can make your match feel special; just make sure that it jives with the discussion you’ve had so far. Kyle and Tanya’s conversation centered around the snow storm and her need for a wine detox. Suggesting that they take advantage of the weather and indulge in a virgin beverage is not only unique (it’s unlikely that she’ll have this date with anyone else), but it also shows that he can fit into her lifestyle.

MESSAGING MISHAPS

When you’re composing responses to your suitors, remember that there are some topics of conversation you should avoid:

Sex. Even if you’re seeking a casual relationship, putting your bedroom etiquette out there too soon can set the virtual vibe that you’d rather skip the actual date. Unless you’re specifically looking for a no-strings-attached relationship and your only aim is nookie, skip the virtual sexy time.

Religion. The first few emails are not the time to mention (or ask about) religion. Unless you’re on a niche dating site geared to a specific religion, it’s too soon to dive into such heavy territory. Your theories on heaven and hell can come later.

Past relationships. Beginning a new relationship by referring to an old one starts things on a sour note. It’s unlikely that your match will want to get involved with you if it sounds like you’re hung up on an ex.

Marriage. If your ultimate goal is to tie the knot, that’s something to keep in mind as you date online but should not be focused on in emails. It’s getting too many steps ahead of yourself. Keep conversation light and fun until the relationship develops more offline.

Oh-so-personal moments. There are things in life that are best kept as close memories until the right time comes to discuss them. I’m not suggesting that you lie, just that you avoid more personal matters, such as deaths in the family or health issues, when chatting online. It may seem natural to reveal the details of your dad’s death when your match asks if you’re close to your family, but unloading too much emotional baggage or putting your match in a must-empathize position will make the scenario awkward, even if you didn’t mean it to. Save these topics for offline once the relationship has developed.

Children. If you have kids, you should absolutely state it in your profile by ticking the correct box. But unless your children have something in common with a match’s kids (gleaned from his or her profile, of course), there’s no reason to bring up your family. The focus of your email string should be the two of you, so you can get to know each other better and develop a rapport. Discussing your twelve-year-old’s soccer leagues won’t achieve that.

Politics. Whether you lean to the left or the right, these details should be kept for later. If you’re passionate about the topic or volunteer for a party, include that in your profile, but avoid mentioning it in emails. Putting where you stand out there is one thing, but discussion has potential to shift you into debate territory, which can rub one (or both) of you the wrong way before you even meet in person.

eFlirt Byte: According to a study by the University of Miami, only 14 percent of singles even bothered to check off their political interests in their profile preferences. It ranked twenty-third out of twenty-seven interest categories—just below video games.

When you encounter a mute match, lead by example.

Occasionally, you’ll attempt chitchat with a match of few virtual words. Remember that not everyone is as confident as you. Lead by example: the more you write, the more you should get back. If your initial message to your match was three lines, and he or she responds with one, make sure that your next email is a bit longer, say, seven sentences. Also, switch strategies and ask an open-ended question rather than something that can be answered with a yes or a no. If this doesn’t lead to more discussion, ditch the conversation. If a match isn’t willing to converse on the Web in more than twenty words, it’s unlikely that he or she will put effort into offline dating, either.

Don’t break up with someone before you even say hello.

Not all emails are created equal. There will inevitably be matches that enter your inbox whom you’d rather avoid. When someone you don’t see potential with crosses your monitor, it’s OK not to engage. While it may sound harsh, there’s no need to respond unless you want to.

In the dial-up days, it was standard to respond to each and every message with a “Thanks, but no thanks.” But while responding this way might seem like the nice thing to do, it can often bring out the worst in people. Against my advice, Sage sent her match a “Thanks, but no thanks” note, and this is what he wrote back:

From: RomanticCynicNYC

Sent: August 19 3:21 PM

To: beingeve

Subject: RE: Favorite Spots

Well, why?! The site says we’re a 98% match. I’m not just some short, lame guy, I’m a good guy. Why won’t you go out with me? Whatever, forget it. Good luck with some dumb jock because that’s the only thing you’ll be able to get. You’re not even worth typing this. Honestly if you think you’re a 10 you’ve got to be joking. Max 5. I can do way better. Good luck with those horse teeth.

She was close to tears when she called me after reviewing this blow to her single gal ego. I advised her not to respond and to hit the Block button (although the horse teeth comment made her self-conscious for months).

If a match is mean, immediately block.

There are few instances when you should block a match. If you simply didn’t jive with someone offline but consider him or her a good person, there’s no reason to get Block-button happy unless this person is badgering you. But when people flare their digital nostrils and get mean, make sure they’re on your short list of people who can never contact you again.

To avoid negative nellies, only respond to matches you’re not into if they write particularly long and thought-out messages based on your profile. People who put a significant amount of thought into messaging you will likely be more hurt by silence. Engaging in conversation brings false hope and allows them the opportunity to lash out. If you do feel the need to respond, keep it simple. Thank them for the messages, mention that you don’t think that you’re the right match, and, of course, end by wishing them well.
Transitioning Offline

The ultimate success of online dating is going on awesome dates and, if you’re looking for something serious, a relationship. But that won’t happen unless you get offline. Your opinions of your match might shift when you see each other’s facial expressions and body language. You’ll either develop chemistry on a more personal level—or not.

Take things beyond the broadband and meet up after six messages total. After you’ve written three emails to your match, it’s time to get offline—any more, and you risk creating an entirely Web-based relationship. Six is enough to get comfortable with each other and should leave you wanting to know more. But men and women tackle these situations differently, so let me break it down by gender.

GENTS

Women want to be asked out. Trust me. Shy-guy routines don’t translate to the Web, so simply ask her out. Since you’ve already communicated back and forth, it’s unlikely she’ll reject you at this late stage, so you should be confident in yourself when sending this final email.

The difference between asking a woman out in person and doing so online is in the phrasing. In fact, you don’t ask. Write her a normal, conversational email, and end with a statement about meeting up. Then ask when works best for her. Kyle used this technique.

This formula continues the trend of making it easy for your match to click Reply. But more important, it projects confidence, which can often get lost when you’re hiding behind a laptop.

LADIES

I know it’s not ideal to ask a guy out, but remember that online dating is an entirely new way of wooing. Men don’t always know how to ask you out (or if they do, they might be too scared to ask). Even though online communication seems black-and-white, there are still a lot of gray areas. So don’t be afraid to take matters into your own hands.

Although the rules for guys can work for you, too, keep in mind that there can be some differences. For example, you can skip the six-message rule if your messages are more in-depth and you’re spending more than five minutes to compose a response. In some cases, requesting to meet might happen during your second message rather than your third.

But if you’re not comfortable being the one requesting a date, nudging him to ask you out should work like a charm. Here are three ways to give him a virtual signal that all systems are go:

1. Mention something current. It’s cool that you bonded over your favorite museums from your profiles. But in order to meet in person, you need to remind him that you’re here and now, not merely an online pen pal. Mention a current art exhibit, what you’ve heard about it, and that you’d love to check it out. Then ask if he’s been. Hopefully he’ll mention that you should head to the museum—or whatever activity you’re discussing—together.

2. Bring up the weekend. Mentioning the weekend is a surefire way to get your match thinking about asking you out; talking about life’s happenings offline reminds him that moving things along with you means meeting in person. Ask what he’s up to during his time off, hoping that he’ll respond with his plans and the possibility of including you in them—even if it ends up being for Monday. Most first online dates take place after work, which will encourage him to include you in his plans the following week.

3. Be bold. If all else fails, you’ll have to be digitally daring. When subtle hints don’t work, simply say that you’d love to meet. The trick here is to make it a statement, not a question. That way, when he responds, he can officially ask you out.

Regardless of your gender, if your match says that he or she will be out of town, has a serious deadline, or anything else that signals preoccupation, keep the conversation going in the meantime. Just be sure to ask him or her out when the busy spurt winds down. If there is some lag time between your last message and date night, don’t feel the need to fill the void with chatter. Once you set up the date, there’s no reason to keep in touch until you get offline—unless, of course, it’s to confirm plans. So nix any random texts or messages without a purpose. Your next connection should be face-to-face.

PHONE VERSUS MEET-UP

Remember that everyone has his or her own preferences, too. Don’t be caught off-guard if a match asks to talk on the phone before meeting up. People have different comfort levels with meeting people they encounter online. In urban areas, singles typically prefer to meet without chatting on the phone, and in fact, I usually recommend skipping that step. If you both lead busy lives, it can become challenging to catch each other for a conversation and become yet another barrier to connecting. While spending more time on email and on the phone can help develop the relationship, it also can be a waste of time, because the only way to truly connect is to meet offline.

Gail messaged with Stewart for a week before they got offline, and by then, I could tell that she was infatuated with him. She owns a fashion company and enjoys evenings at the symphony. So she was turned on by his duality as a hedge-fund partner and a violinist. When he sent her recordings from his recent recital, her enthusiasm seemed to double. But even though they chatted on the phone, all of that chemistry disappeared on their date—the mutual-attraction factor simply wasn’t there. It’s easy to build someone up in your mind before you meet, so pump the brakes until you get in person.

There will be times when an email string will leave you feeling iffy about your match’s potential. In cases like this, the phone is your best tool. Suggest chatting on the phone if you’re on the fence about your compatibility. Keep the call around ten minutes, which should be plenty of time to determine whether a date would be wise.

Remember that emailing with matches never obliges you to meet them. If you’re not feeling it at any point in your email string, kindly bow out. First, go silent on your email string. If they persist and begin pestering your inbox with multiple messages, mention that you’ve enjoyed chatting but are speaking with someone else right now—which you are! Communicating with other matches simultaneously is necessary. But in the context of this email exchange, mentioning as much is a polite yet definitive way of discontinuing the convo. It’s important that you don’t waste your time—or theirs.

Emails create touch points for date conversation.

Remember, the ultimate reason to email with potential dates is to get a sense of each other’s personality and to develop a bond. Although email exchanges may seem trivial, they actually lay a foundation for relationship development and will save you from awkward silences on your dates.

When you keep this in mind, you won’t feel as if you’re diving off the dating deep end. Trust me, when you’re sixty-three and divorced, like my client Corinne, meeting someone from the Internet can cause major first-date jitters. When she last dated, the Internet didn’t even exist, never mind the notion of meeting a stranger after a few messages. To her, the Web was a place she visited exclusively for work correspondence and photos of her grandkids, not a meet market. But she knew that online was where the singles her age hung out. When she had a sudden flash of panic before her first date, she called me and ranted about how she knew nothing about the person who was about to be on the other side of her table. I calmed her by reminding her that she actually knew a lot about him from their email exchanges. And trust me, this isn’t something only older singles experience. Even the most tech-savvy twenty-somethings freak out about the lack of information they feel they have about a match. When your mind goes into overdrive, remember that online dating is all about getting to know someone new and that you’ve chatted previously. You can refer back to email anecdotes to fill the silence and to delve deeper into what makes him or her tick.
Following Up

While it’s simple to send a message off into the Winkiverse, it’s not always as easy to obtain a response. But all hope is not lost if you don’t hear from your match. There’s a secret to the trade that not everyone knows: the follow-up message. After all, in the world of cyber-love, lots of factors can deter matches from emailing you back:

They’re busy at the moment. You never know what’s going on in other people’s lives. It’s a common misconception that if someone logs on, reads your email, clicks through to your profile, and doesn’t respond, it means he or she isn’t interested. Not always the case! It may simply be that the person didn’t have time to write you back then but might get to it later. Keep an open mind.

Their dating calendar is full. Just because your match has an active profile doesn’t mean he or she is actively dating. Matches may be checking messages, but their dance cards might be full. When a dating calendar gets full, matches will sometimes wait a while to respond until things cool off and they’re ready (and eager) to meet someone new.

They don’t pay. Most paid dating sites allow all members to have profiles, but only those who pay for a subscription can message. Just because someone showed up as a match and has logged on recently doesn’t mean that he or she is a full-fledged member who can reply to you.

You got lost. If his or her inbox is a virtual hot spot, your message might have been buried or deleted before it was even read.

Your profile wasn’t good enough. If your photos were unclear or your text wasn’t specific, you might not have made the cut. Hey, everyone has different preferences!

Online dating takes persistence. Of all of the scenarios above, the only real potential blow to your ego would be if your profile didn’t resonate with your match; all others are the result of miscommunication or unlucky timing. Make sure you stay on the same page—literally and figuratively—by sending a follow-up to get your match’s attention. Since each scenario is different, below are the three that my clients most commonly encounter and easy troubleshooting tips:

1. The 10/3 rule. If it’s been more than ten days since you emailed and the match has logged on within the last three, it’s OK to send a follow-up. Never send back-to-back messages without a large time lapse like this and knowing that the other person signed on recently (if that functionality is available to you)—it will seem pushy the next time he or she logs in. The goal is to keep your follow-up short and sweet, with no negativity or guilt trips. Let the match know that you’re still hoping to connect. However, be prepared for it not to always go your way. Your match might respond, “Best of luck” . . . or not at all. If he or she does read it and doesn’t answer within a few days, at least you have closure, and you know it wasn’t simply a missed connection.

2. Revamp your stats. If it’s been a while since you’ve updated your page, think about uploading some new photos, revising your profile, and updating your preferences before reaching out again. Refreshing your profile page can often elicit responses from matches who may have previously passed you over.

3. Disappearing act. If you were in the middle of a great email string and your match suddenly vanished, see if he or she has been online recently rather than wondering where in the World Wide Web they went to. If so and it’s been more than five days since you last heard from the person, respond to the email string again and see how things are going. The lack of response was likely an accident.

Above all, don’t take it personally! Jumping to conclusions will only make the online dating process more challenging.

Remember that dating is about flirting, and doing that over emails requires a coy tone devoid of sarcasm. Make your messages light and fun, but delete cheesy pickup lines from the screen. These don’t work in person, and you won’t fare much better if you’re dishing them digitally.

Emailing gets you both offline. While you may feel tingles through your iPad from your match’s words, experiencing that spark in person will lead to an offline relationship—no Winks necessary.