Advice

Tom Shone decided to give internet dating a try after breaking up with his girlfriend a month before. Guess who was the first person to contact him on a dating site? If you said his ex-girlfriend, you would be right.

Loved your profile on Nerve. Glad to hear you’re feeling so “chipper” these days – Natalie.

Tom hadn't meant for anyone who really knew him to read his profile, especially his ex. You always put your best foot forward when writing a dating profile, which made it look like to his ex-girlfriend, that he had forgotten all about the heartbreak and tears from the month before. She did later apologize that day for the email, and said it was just a shock to see the profile. Tom told her that he wasn't using the dating site to go on dates, he was just window shopping.

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.

Craft an online dating profile. Remember, your profile isn’t for you – it’s for your potential dates! Seth Godin, marketing genius, once spoke to the folks at Google about cat food. You see, cat food is not for cats. Sure, it provides nourishment for cats, but cat food is really for people. If cat food were for cats, it would come in Freshly-Dead Mouse flavor. As it stands, cat food comes in flavors like Grilled Salmon. Know any cats who insist their salmon be grilled? I sure don’t!

Think about the things that you’d want a potential mate to appreciate about you and do with you. Write about these things with passion and the most descriptive language you can. Paint a picture of a life that your ideal mate would love to jump right into and experience with you. And remember, marketing isn’t about lying. (It can be, but it’s not in this case.) It’s about putting your best face forward and writing for the audience you hope to attract.

In that same vein, choose recent and appropriate photos. Those shots you took in the dark with your webcam, or that you doctored up with various photo editing programs are not the photos you want to use here. We’re talking high res, good quality photographs. If you can get professional photos taken, awesome. If you can’t, hand a camera to a friend and have them take pictures of you doing what you normally do.

Choose one or two dating sites, no more. I recommend one free and one paid, but that’s up to you and your budget. Why two sites? You’ll find that the vibe and the membership of your sites will be a bit different and eventually, you’ll figure out which one works best for you. Oftentimes, people start with one site and throw up their hands in frustration after three months of little to no luck. “Online dating sucks!” they claim. “The people I want to date don’t write me back and the people who write me I wouldn’t touch with a ten foot pole!”

I tried several sites when I was making my rounds as a single girl looking for love. I found that Match provided the best results for me, eHarmony often matched me with the same folks I found on Match (for double the price!), PlentyOfFish was full of folks wanting no-strings sex, PerfectMatch didn’t live up to its name, and OkCupid just didn’t quite have the right people.

Your mileage, of course, will vary. I have clients for whom the exact opposite is true. Match and eHarmony don’t have the right people and OkCupid is swarming with folks that they are attracted to and want to date. Don’t judge a dating site by the review of one or two people who found it useless for them. Get a balanced view by reading and asking around before choosing two sites to try. Don’t forget to look for special coupons for free weeks!

Sites I recommend include:

• Traditional Online Dating: Match.com (read Review)
• Free Online Dating: OkCupid (read Review)
• Matchmaking/Personality Test Based Online Dating: Chemistry (read Review), eHarmony (read Review)
• Niche/Religious Online Dating: SoulGeek (geek dating), ChristianCafe (Christian Dating), JDate (Jewish dating)

Just because I don’t personally recommend a site doesn’t mean it’s not good. My biggest advice would be to avoid the tiny niche and white label dating sites (see Story). Stick with the well-known sites, pick two sites to focus your attention on, and start writing that profile!

Related Stories:
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 4: Emails and Winks
The Roadmap to Online Dating Success, Part 5: The Daily Grind

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).