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March 13, 2008

You may have noticed an uptick in blog posts. That’s because I’m currently unemployed and find it easier to write long blog posts than to drum up clever cover letters. Mine are as dry as melba toast. Ugh. It’s awful. I finally broke down and bought a book called “Dynamic Cover Letters” by Katharine and Randall Hansen. Besides posting several sample winning cover letters, they dissect some truly terrible ones to highlight the do’s and don’ts.

This got me thinking about an email I received from a Matchman some time ago and for whatever reason saved in my inbox. It wasn’t the worst email I’ve ever received (Sylvia and I must get started on a “Hall of Shame”). It was one of the saddest, though. It was also quite effective, if his purpose was to clearly communicate that he was (in his own words) a stupid, bitter, hollow shell of a man who turned to Vegas for comfort.

I’ve included the email below, and what I learned about writing good online dating emails.

I think Homer (Simpson) pretty much summed up the way I have been thinking lately…”Bart, with $10,000, we’d be millionaires! We could buy all kinds of useful things like…love!”. That seems to fit in so many ways. First, sometimes I can’t believe what an idiot I am (I just have to sit back and laugh), and second, it seems like all the women I have been meeting lately are high maintenance.

Since I am sure it is a turn-off (and you must be curious), after about a year of “trying to work it out” my wife and I have decided to call it quits. I guess I used to have a job where I traveled 80% of the time and woke up one day and decided I no longer wanted to work 70 hrs a week. I changed jobs where I work from home and have a flexible schedule. I guess that is when she decided she liked the idea of me better then actually having me around. 😉 While I am ready to move on, I would be lying if I said I was completely over it. So I am not ready for the big nights out, but am ready for a cup of coffee or a walk in the park. I already realize that the pleated pants are out (should I replace them with pleated shirts?), and a few weeks ago, I went to a good hair dresser who told me I shouldn’t be using the gel I was. Go figure, who would of thought of clay…you could have saved me a lot of time and probably increased my social image!

On a side note, I just got back from Vegas with some friends where they signed my up for (one of them recently got married from a girl he met here). So I figured as I sit here and try to piece together the shattered remains of my soul (Vegas has a tendency to rip it apart) I thought I would drop you a line and say hi. I am getting ready for another trip (didn’t I say I don’t travel anymore) but would love to exchange a message or two while I am away. I am seriously contemplating a cross country trip. If you have a recommended stop or two, let me know.

I am sure you get about 20 messages a day, but I hope you take a second to reply.


Email 101
First thing’s first: An introductory email should be no more than 10 sentences. You need just enough to pique someone’s interest. You have plenty of time to scare them away later.

It should be tailored to the person you’re writing to. Everyone can spot a form letter- if you’re looking for someone who’s equally uninterested in getting to know you, then by all means, keep sending them.

I’ve included some pointers, along with how I would have rewritten Mike’s email:

Step One:
Say something that the reader might find interesting or funny to break the ice. If it’s related to something they mentioned in their profile, all the better.

“This whole online dating thing reminds me of a quote from Homer Simpson… ‘Bart, with $10,000, we’d be millionaires! We could buy all kinds of useful things like…love!’. I hate that we’re all paying some site 30 bucks a month to set us up on dates! But, hey, Match works… I have a friends who married a girl he met here.”

Step Two:
If you are in a situation that you feel needs to be explained, mention it here.

My wife and I recently separated, so I’m not ready to dive in to a relationship right now, but I would like to dip my toes in the dating pool and meet some nice people.”

Step Three:
Most importantly, include one or two things that establishes a connection.

“You’re a coffee freak too, huh? Have you ever been to the C & C Coffee Factory on Main Street? The owner has the cutest little pug that hangs out on the porch.”

This totally sets you up to ask for a coffee date. I just added the pug ‘cuz girls love little dogs. A friend who shall remain nameless suggested that you should work the following surefire words into your email: monkeys or pirates. Why? ‘Cuz who doesn’t like monkeys and pirates

Step Four:
Ask a question that’s related to their profile to get the conversation going.

“So, I read in your profile that you took a cross- country trip? I’ve been seriously contemplating one myself. What’s the one story from your trip that you just can’t stop telling people?”

Step Five:
Sign off. Avoid the “I’m not really worth a response, but I hope you’ll write!”

If you must, say… “looking forward to hearing from you”…

Go forth and give this formula a shot. If you’re not getting more responses, you let us know. We’ll send you more words, like “ninja”. Genius.

When you’re ready for email writing 201, check out Evan Marc Katz (if you don’t have him bookmarked already!) and his article about writing introductory emails: Writing Introductory Emails That Get Response

2 Comments leave one →
  1. March 18, 2008 12:58 PM

    Your advice is great for match or eharmony, but I don’t think it would work so well for

    Trust me, I tried everything. Thanks anyway though.

  2. winniesylvester permalink*
    March 18, 2008 6:03 PM

    Point well taken. Mentioning cute puppies and walks in the park isn’t going to get anyone very far on I was going to make some point here about the basic principles of introductory emails being the same no matter where you get your freak on, but the writing on your blog shows me you graduated from the 101 class a long time ago.

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