The Roadmap to Online Dating Success, Part 4: Emails and Winks

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