Email Writing Tips: how to be funny and interesting!

This week, a question from one of my long term readers:

“Hi Dylan:
A thought and response to your latest weekly e-mail. Specifically the following quote:
"write an email that catches her attention by being interesting, insightful and funny."
Give an example of one such e-mail, better yet, give a before and after version.
Here is my challenge to you: Take an average e-mail, that was sent out and then re-edit it with a commentary afterwards.” - JN

Hey JN!
Well, like all real men out there, I can’t turn down a challenge, dare, double dare, etc... However, you didn’t send me an average email to re-edit, so I’ll just start with your average bad email. It goes something like:

“Hi, I saw your profile and you are really cute! I like your hat in that picture, it’s really nice, where did you get it? Anyway, come take a look at my profile and if you like what you see, email me!”

This email can be broken down into three parts. Crap. Crappier. Crappiest.

Sentence 1: Crap
Average guy saying an average thing. If you’ve been a long time reader, you’ll know that “cute” is one of the words I’ve banned from your vocabulary as a future Online Casanova. (The others are Hot, Sexy and Nice) It’s so... average. And average is death.

Sentence 2: Crappier
“I like your hat” is a good example of the bad online dating advice given out by MSN and Yahoo online dating “experts” (COUGH). They say “find something in her profile or photo and ask her about it.” That’s great if you want to be her friend, but it doesn’t make any kind of connection, so forget that nonsense. I’ll tell you what to ask about in a minute when I’m doing making fun of the bad email.

Sentence 3: Crappiest
95% of bad first emails end with “come take a look at my profile”. You want to end your email with a command, not a request. Salesmen and marketers call it a “call to action”, like “BUY NOW!” Whatever... anything is better than a passive and wussy “come look at my profile.” You’d honestly be better off ending it with “zombie monkeys are eating my fingers as I type, email me back or they’ll finish me off!” Actually, I kind of like that. Anyone want to test this one for me?

SO...
That’s what makes a bad email.

Let’s make a good email. JN asked about how to be interesting, insightful, and funny. I’m going to teach you to be both funny and insightful... do both of them together and you will also appear interesting, especially compared to the masses.

Point 1: How to be funny
There is a current trend amongst guys to go with a “shock her” type approach when they are meeting women, where they are a little bit cocky, a little bit funny. (I’m trying to avoid actually saying “cocky/funny” as coined by David DeAngelo, OK?) Here’s how to do it in email.

First, read her profile up and down, back and forth. Pick out something that is completely unique to this girl, and forget all the stuff that you’ve seen in dozens of other profiles. Example: She says, “I’m smart, funny, unique, love baseball, study medicine, and also work on a chicken farm.”
Forget everything but the chicken farm. The chicken farm makes her unique! This is what you want to focus the first part of your email on. Call it your opening paragraph hook. Try to let your brain come up with the craziest, funniest observations you can. My brain is a little sluggish right now, but I might write something like:

“A chicken farm? I love chicken! We’d be the perfect couple... You could poach extra chickens from work and I could fence them on the chicken black market. Eventually we could build up a nest egg and flee the coup to sunny Chichen Itza!”

Wow, that’s a bad set of puns, even for me. Stupid brain... Anyway, you get the picture. You are touching on what makes her unique, the little point that most guys ignore to go for the easy and mundane stuff like “I like your hat.”

Point 2: How to be insightful
If I lost most of my other online dating skills, this would be the one that would keep me in the game... reading subtext into her words.

Guys don’t really read profiles. Sure, we skim them over a couple times and look for points to talk about, but we don’t read between the lines. We don’t really look for the depth of her words, the subtext of what she is really saying... what she is really asking for. Let’s go right to an example.

Here’s a section of a woman’s profile:
“I’ve been here before, perhaps to many times, each time a little more jaded. If only we could be more honest with each other, the world would be a better place. I’m looking for a guy who is kind, faithful, and sincere.”

And the subtext says....
“I’ve been hurt by men.”

How did I get that out of the above paragraph? Look what she’s saying: she’s come back time after time, even more jaded, which means she’s gone through numerous relationships, each of them having ended with her getting hurt. She’s wishing for more honesty, which means she’s faced a lot of deceit. And she’s looking for a guy who is kind, faithful and sincere, which heavily suggests that she knows what she wants because she’s done time with a lot of guys who have been unkind, unfaithful, and insincere to her.

So, I see this profile and I see a girl who has been hurt, and I know that she will respond to... a guy who is kind, faithful and sincere?
NO!
She’ll respond to a guy who UNDERSTANDS HER! Forget everything about what women want on the surface! Deep down... they want to be understood (we all do). Being a guy who understands who she really is and sympathizes with her is so much more powerful and rare

To address that, I would write something like:
“I read your profile and couldn’t help but feeling a twinge of sadness at your words. We all seek happiness in life, but disappointment certainly seems to find its way in often enough. Like you, I simply seek a bright sunny day in a cloudy world.”

This wouldn’t be my whole response of course, but it would certainly get her attention away from the guys who write “I’m sincere, honest, and faithful.” You know... the same ones that hurt her in the past?

So...
You asked how to write a funny and insightful email? Combine those two techniques. Pick out the little unique gem in her profile and make it shine with humor, and read deep into the subtext of her profile, find out what she is really saying, and sympathize with it.

What... you thought it would be as simple as writing “who lies more, men or women?” :)

Well, this has been my longest post ever, so I’m going to wrap it up here. If you’ve got any questions, email me at onlinecasanova@gmail.com

Also, I have a whole chapter on email writing in the Online Casanova book that covers the do’s and don’t, and ways to create connections and deep bonds with a woman through your emails. If you want to learn the rest of my techniques and email writing tips, you’ll find them at http://www.onlinecasanova.com/

Cheers and happy dating!

Dylan Alexander