Communication

Now that you've set up your searches and favorited some interesting people, it's time to send some emails!

Set a reasonable rate of emails per week. For my Gold clients, I send 10 first contact emails per week. Ten is a good, round number and prevents you from getting into an assembly-line kind of feel for email-writing.

Favorite first, then email later. This prevents you from going into email overdrive because you’re afraid you’ll forget to email someone. It is very doubtful that waiting ONE DAY is going to mean the person of your dreams slips through the cracks. And if they do, well, it just wasn’t meant to be.

Think of it this way. You email someone one day too late. It’s a well-crafted, well-thought out email. They think:

“DAMN! That person is great, I’m kinda bummed I’m dating someone. This person sounds way cooler. Maybe I’ll cancel next week’s date and go for this one...”

Option B! You go beyond your ten emails a day because a new member popped up that you just had to email because they were just too perfect and awesome. Problem is, you’ve already written a bunch of emails so this one (whether you realize it or not) sounds a little... canned. They think:

“Hmmm. Yeah, not really.” Delete.

Sticking to a maximum of ten emails a week ensures you craft each email individually. Cut-n-paste emails stick out for bad reasons. Make yours stick out for being thoughtful and unique.

Think of it like a cover letter for a job. You want it to have immaculate spelling and grammar, but you also want to convey your enthusiasm for the company and the position they have available. The more you can connect your skills to the company, the better your chances are of getting an interview. Obviously, you’re not REALLY applying for the position of girlfriend or boyfriend, but your goal should be to get the person interested you and the way you could possibly fit into their life.

Don’t wink, unless it’s right after emailing. You can combine an email with a wink, but don’t ever wink alone. Winking is the easy way out. Why spend time writing an entire email when you can press one button and move to the next 35 profiles? It’s like casting a wide net and seeing what you catch, right?

Wrong. Winking sends a message. It says, “You’re not worth an email.” It says, “I’ll see if there’s anything in this for me before investing my time.”

Always email first. Send a wink along with the email (or in a day or two if you haven’t heard back), but never wink alone.

Next up, setting up a routine so the daily grind of dating doesn't grind down your resolve or your eat away at all your free time.

Related Stories:
The Roadmap to Online Dating Success, Part 1: Choosing Your Site
The Roadmap to Online Dating Success, Part 2: The Perfect Profile
The Roadmap to Online Dating Success, Part 3: Before You Send Any Emails
The Roadmap to Online Dating Success, Part 5: The Daily Grind

I know, you're excited to start checking people out and sending emails and (oh, please don't!) winks. But hold your horses for just a few minutes and do these things first to set yourself up for success.

Check your profile once it goes live to be sure everything looks good. Tweak if necessary. You may find that your profile looks different when it’s up on the site. There may be a one word line at the end of a paragraph that you could remove with a little careful editing. You may realize that your chosen headline cuts off in the preview mode in an inopportune spot. ("You know you want to see my furry...... *click....loading, please wait* ...new puppy!) These are all things that can be neatened up in a few minutes before you get down to the fun part.

Set up your account preferences. Many sites allow you to customize what members can see you and email you. For example, PlentyOfFish allows you to block members who are only interested in casual encounters. OkCupid allows you to specify exactly what kind of people can send you messages, so you never have to worry about getting emails from people who live across the country, are way too old for your liking, or who don’t match you by at least a certain percentage. Match.com allows you to block certain users, for example, your exes, your coworkers, or anyone else you don’t want messing with you while you’re busy searching for love.

Many people ask me, "How do I know when to ask someone on a date? I've been emailing with them on my dating site, but I don't know when the time is right..."

This is at once a very easy and very difficult question to answer, but let's give it a whirl! (Disclaimer: This method is not one-size-fits-all. Your mileage will vary.)

You write a first contact email. It's short, sweet, personalized to their profile, and ends with a question for them to answer. They write you back to say, "Thanks, but no thanks." Do not pass go, do not collect date.

You write a first contact email. It's short, sweet, personalized to their profile, and ends with a question for them to answer. They write you back and answer your question, but do not ask any of their own. Write back, continue to show interest, but do not pass go, do not collect date (yet).

Having used various online dating sites for the past seven years, there’s really not a lot I haven’t seen come across my inbox. From winks from other women (daring, I applaud you) to hate mail, I’ve taken the time to read each and every message people have been brave enough to send my way. But I didn’t respond to all of them. Mostly out of a lack of time, but other times, there just wasn’t anything I could find to say that was…right. So, from a girl who has used online dating to all of you guys out there, here’s some insight as to why I didn’t email you back.

Grammar and usage. Anyone who took the time to read my profile will know that I’m a writer for a living. Grammar and usage are high on my list of “needs” from a partner. Granted, that’s not everyone’s strong suit. I get that. But when your email to me looks like you dropped the Manhattan yellow pages on your computer keyboard and hit “send,” I’m pretty unimpressed. If you’re not a great speller or even writer, take the extra minute to write your email in a word processing program (or even over in Gmail or Outlook) that has a spell check feature. Copy and paste the proofed email into the online dating site’s form and then click send. I’ll thank you a million times over! By not doing this, you’re telling me that you don’t respect what I do for a living. I’ll understand if you’re not Hemingway if you understand that I need you to understand the difference between “your” and “you’re.”

I stumbled across an interesting story today through a link shared on Twitter. To say that it was inaccurate is an understatement! I'd like to bring up one point that the writer makes and let you know exactly why he is 100% wrong.

Here's what he writes about winks:

Do: Wink as often as possible. Most sites offer a free communication tool called a wink (or a flirt) where members can show interest in each other with a pre-written email designed. Since winks are the primary method by which other members will notice your profile you must get in the habit of sending a lot of winks. Send 10 winks per weekday for 1 month you will have sent 200 winks. If only a mere one percent of all members at whom you have winked showed interest, you'd meet two brand- new love interests every month.

Don't: Email before winking. A direct email before attraction is solidified is as welcome as a phone call at dinner time. Doing so exemplifies a non-interest in attraction and may irreversibly turn-off a potential mate. Conversely, don't pre-judge an attractive profile due to some personal neurosis. If you see someone you're attracted to but they live in Magna- wink anyway. You never know what treasure's you'll find if you keep digging.

Wow. Just wow. I'm not sure how he could be more wrong about winks. Here's how I would re-write the Do's and Don't's of winks:

Do: Send a short and sweet email to people you are interested in. It shows that you invested time in reading their profile and crafting an email that addresses them directly as a person, not just as an attractive target. Send 10 emails per week to the people who interest you the most. If you must click the wink button, do so immediately AFTER sending a first contact email. Winks and emails can come as a package, but a wink shouldn't come separately.

Don't: Wink at anything with appropriate genitalia and a pretty/handsome face. Ten winks a day? 200+ winks a month? This clearly indicates you are not being selective or reading your potential match's profiles thoroughly. Sending a wink with no email sends the message, "I think you're cute, but I don't want to take the time to write you unless I know it's worth my time." Essentially, you're telling the person, "You're not worth it right now." I think that's far worse than sending them an email and risking coming on too strong. (Besides, with the right first contact email, you'll only come on as friendly and low-pressure.)

What do you think about winks? Have you been a victim of a drive-by winker?

This time OkTrends took a look at almost 1 million people and their messaging habits on OkCupid. What they found may shock some people:

A message sender's race is a huge factor on the average reply percentage.

Here are a few interesting points they raised:

• Black women are the most talkative. They are more likely to reply to your message, about a quarter more than other races.
• White men get more replies from almost all groups when then send a message to someone on a dating site.
• White women prefer white men but Hispanic and Asian women do more so.
• Men don't tend to write black women back as often as the average response rate.
• White men are rude to all races. The average response rate of a white male is 40.5% across all groups but the average response for non-white men is almost 8% higher at 48.1%.

Visit the OkTrends for the complete details on this story including easy to read graphic charts. To find out about OkCupid, read our review.