Crafting the Perfect Email


When I joined a few years ago, it was for one girl: Shadoe987. Sweet sweet Shadoe987. So lovely, so innocent, so eccentric in her spelling choices. I had taken a half-hearted swing at Match a few years previous, so they had me on their “bother to the point of certain insanity” email list. They sent a plea with a silly headline like “Look at All You’re Missing Out On!”, then a simple little picture of Shadoe987 and a few sentences about her and, well, it got me hook, line, and also sinker. “Yes, look at what I am missing out on!”, I said to my cat as I happily entered my credit card number. There was just something about Shadoe987, she was so…attractive, so wholesome, so forgiving. The kind of girl who would absolutely not judge you for being duped by yet another promotional email from a company you had no interest in. So I signed up for Match, fired off a carefully crafted message to Shadoe and a few other incomparable young women and waited for the responses to come rolling in. And you know what happened? Jack shit.

I never heard back from Shadoe987. Who knows where she is now…maybe living in Paris with her playful yet reliable husband who’s taught her more about wine than she ever imagined. Or maybe she died in a horrible farming accident. One of the two. But I will always remember her fondly for the lesson she taught me: Internet dating is a numbers game. Because after I didn’t hear back from Shadoe987, I emailed fifteen or so other women with a far less carefully crafted message and you know what? Five of them wrote back. Five! That’s a lot of people. Sure, ten totally ignored me, and the subsequent dates resulting from those five ladies were awful BUT…I got five dates. In a half hour of work. And suddenly my mission was born: create the formula for the perfect introductory email and send it to as many women as possible.

Every person you write.

Look, if you wanna send every person you meet online a deliciously personal email that it took you twenty minutes to craft out of thin air – go for it. You’re a gentleman and a scholar. But you’re also an idiot. I’ll say it again: Internet dating is a numbers game. And they’re not small numbers, they’re really really big ones. It is more likely that the person you’re writing WILL NOT write you back, no matter how charming and eloquent you are. Believe me, Shadoe987 got every bit of my charm and eloquence and she didn’t even thank me before she was killed under that tractor. So in order to be an effective Internet dater, your first email should be something quick, delightful, and seemingly personal which then allows you to move on dot org. That something can be an easily forgotten two line message OR it can be the most genuine and well-intentioned form letter in the history of the written word.

Listen to what I’m going to tell you now – the recipient CAN NOT know that you are sending them a form letter. If they do, you’re done for. I’ve seen some mass messages that men have sent thinking they’re carefully disguised, and it’s enough to make you weep. Long paragraph that’s just about them? Form letter. Vague platitudes about how “pretty and cool” the lady seems? Form letter. Random jokes about how crazy the world of Internet dating is? Form letter. And last but not least: long, rambling love poem in broken English that gets uncomfortably sexual in the final stanza? Sadly, that was also a form letter. How do you avoid making your email look like a form letter? By not making it a form letter at all.

A form letter that’s not a form letter?! Brilliant!

A form letter is repeated word for word to each recipient. What I have instead is an equation, and it is perhaps my greatest Internet dating secret. The perfect introductory email has taken me years of trial and error to develop, and got so good that at one point my response rate was up to 50%. That’s right: 1 in 2, motherfuckers. It’s my best friend, and I know every step of it by heart. If I ever get sent to some awful prison in a Midnight Express-type situation, my introductory email is what I will recite in my head to keep myself sane. Some men put their children on their knee and tell them about the time they scored the game-winning touchdown in the big homecoming game, I will tell my son about the time I created the perfect email that let me meet only fantastic women. OK, a few fantastics and a lot of crazies. Now I pass on the formula to you, guard it with your lives.

Part 1: A Little About Them

This is where the magic happens. Read your future betrothed’s profile, find one thing about it you find funny or interesting, then write two sentences. One sentence is too little to make an impression, three sentences is desperate hand-wringing, two sentences is just right. This is real, this is genuine, this must be original for each person you write. See, not a form letter!

Part 2: A Little About You

If you’re a cad, you can copy and paste this section every time. I preferred to create from scratch in each email, but my goal for the portion was the same…

In as funny a way as possible, tell them a little about yourself, accentuating your most date-able characteristics. If you’re tall, work it in casually. If you do something heart warming and awe-inducing like teaching deaf kids, subtly drop that hammer. If you’ve got a great rack, just come out and say it, guys will probably forgive you. Sell yourself in three sentences MAX.

Part 3: Say Goodbye

That’s it. Say goodbye and sign your name. Plain and simple.

Seems so simple, so obvious, but it’s not. You’d be amazed at how many people’s first emails are a complete disaster. They write one line, then hit send. Or, even worse, they write six paragraphs, cry a little bit, then apologize, then cry again. Nothing more awkward than a tear-stained email. The perfect intro message is so basic: talk about what you like about them, what you think they’ll like about you, and get the fuck out.

Don’t mess with me.

Is it dirty pool to use a formula on someone I genuinely want to go out on a date with? Yes, a bit. But all I’m really doing is simplifying the task for myself and you, should you chose to follow. I never lie and my goal is always completely genuine: find a good girl. But I’ll warn you, these powers must be used for good and not evil. Should you use my formula to go out with as many people as possible to just feed your ego or get laid, then it won’t work. You’ll cut corners in paragraph one, your reader will know, and you’ll be done. And the world will hate you and a horn will grow out of your head. But use this it to increase your chances of finding the person that’s right for you, and the Gods of love and Internet will smile down upon you.

Unless she happens to be named Shadoe987. If so, let me spoil the surprise – she ain’t writing back.

Good advice, right? For more, buy my new book Not a Match: My True Tales of Online Dating Disasters. 

Available for your ereader on Amazon and iTunes. It’s cheap, and awesome! Please help support the site!

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36 Responses to Crafting the Perfect Email

  1. Denise says:

    I’m borrowing this and we’ll se how my stats go up or not. I haven’t met anyone new in a while and that needs to change.

  2. JW says:

    Great advice to everyone out there who is internet dating.

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  6. Teena Lovern says:

    so true! i support the magic of the form letter and offer several for online/traditional dating on my site!

  7. mcsurly says:

    It took me a while to realize that some non-responses aren’t my fault. You can’t tell who on Match is a non-paying lurker (unless they pay extra for that green border, in which case you should take non-response personally, and be totally offended). Freeloaders can’t reply to emails. They could pony up when they read your life-changing email, but … we just agreed not to send that kind of email, didn’t we?

  8. Jeremy says:

    Am I suppose to say, “Hi” or “hi there” or anything? Do I just blurt out, “I SEE YOU LIKE LATIN DANCING!!! I LIKE DANCING TOO!!!” minus the caps, but ya know for dramatic effect.

    What about the subject line? Is it blank, should I put something awesome up there, like “I’m awesome, true story.”

    • B says:

      Jeremy, I’ll let you handle the subject line and salutation all on your own. I believe in you.

      • Jeremy says:

        wow, I sure hope this doesn’t backfire. Thanks so much for your well written articles. Even if they all don’t apply to my situation I always get a great laugh.

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  10. D says:

    Can you share your email that got your match?

  11. BLB says:

    I just went through exactly the same thing as your first paragraph and have been googling trying to find what the hell I did wrong. Best one if these articles I’ve read, hands down. This advice is getting put to work immediately

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  14. Nancy Booth says:

    Guess I’m more “conspiracy theory” minded than you; how about the possibility that Shadoe987 was some type of plant by Match to get you to join. My cause for becoming a paying member of Match went like this: As a non-paying guest, I poked around looking at various bios and (somewhat ignorantly) marking those I liked as “favorites.” (I found later that the favorited people get notified.) Anyway, when I favorited one man, the system somehow went haywire and sent him multiple winks, over and over again, until the winkee got pissed and sent me an e-mail demanding I stop. Of course, I was only notified that I had an e-mail from an “admirer” so what was I to do but join? Sadly, after I had paid my money and anxiously opened the e-mail, I found it was extremely mean and nasty, stating that he wanted someone much more feminine than me and that he thought I was being foolishly hasty to be seeking men so soon after my husband had passed away (it had been over a year). In retrospect, I’m glad I was passed up by such an ass. Anyway, who knows what really happens in the dating website marketing meetings… I really did like your article, though. It was extremely funny and its good to read that it should not be a personal insult if everyone doesn’t respond. Thanks.

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  16. steve bogatinoff says:

    in part 3 saying goodbye, do you ask her to respond, or make a comment to that effect? or just say goodbye, and your name?

  17. Yuri Rodin says:

    If you have to read the whole profile and think of something to ask/say about it how is that a form letter?? And why would you write something about yourself in the letter? That’s what the profile is for!

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  20. Tonya says:

    So, did you meet the love of your life since you wrote the book? I have met several men and its been nothing but crazy. Either they want you to show them my nickers or they are chronic daters, or they are older than the picture they put on the web site! It’s wearing me out! I’m cute I shouldn’t have to do this bullshit! Oh well, thanks Tonya

  21. Aaron says:

    This article had nodding my head and laughing in a very “I can relate” way. I’ve taken this disconnect up with several women(sisters/friends/etc.). By disconnect, I mean that women expect a thoughtful, personal email. But men don’t want to spend the time writing those because 19/20 times they’ll go unanswered. I’ve met and hooked up with far more women by joking about sex, Cheetos and the Kardashian’s than I ever have by trying to take the time to actually get to know them. c’est la vie, I wish it weren’t true!

  22. Sean says:

    Hi B, great blog entry. I have a couple questions for you. Let’s say that as a guy you receive a wink or a like from a girl you are interested in. How do you go about writing to her? Do you right something simple like “Hey how are you?” or should you send her a short, well-written email that shows you read her profile and point out a few things you have in common with her?

  23. TJ says:

    I have been on match far longer than I care to admit. I live in a really bad area where meeting people is very hard. And it seems this is the only way I can get to meet potential dates. Very good article. I discovered years ago that this online dating thing is much harder for men than women. And it’s easy to see how, many more men are online, looking than women, and women can simply just sit and get all the attention and be as selective as they want. Must be nice! Anyway I found out that for most men it is very much a numbers game! We have to send out tons of emails to get a very small response rate back. And that depends on how shallow we are too! I have to say my response rate is anywhere between 5-10%, but I am very picky. But I think I am staying in my own network so I don’t feel I should lower my standards! I found that crafting that perfect initial message is very time consuming for the resulting response rate. I felt why does it have to be so hard? I wish women would be more open to winks, I think they are great and it’s a great time saver. Why waste each other’s time? You like the man that winked at you? Wink back! Then he can write you that perfect email! I agree form letters are not cool, but then again spending 20 minutes writing that perfect email is also not very productive and a huge mistake–unless you are unemployed.

  24. Stacey says:

    It’s not always so much easier for the women, not even the cute ones. It’s hard not to take it personally when you see they read your email but you have no responses. It’s the equivalent of checking your phone to make sure it’s on and working lol

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  27. David graham says:

    women can seem vain and narcissistic , why wouldn’t they be? With men like you sending huge heart felt emails to someone they’ve never met just because they find them attractive

    Think about the imbalance of your time for her looks , she knows why you have taken this time and effort and it feeds her ego for free

    Be honest , be fearless and wink like crazy
    If she winks back OR views your profile then it’s an email
    My email has 2 lines and I have 7 dates a week from different women
    I have ONE profile pic and I’m no model , a good clear profile pic is 110% of it , you can also craft your profile as the archetype of what women like (buy a romance novel)

    Sounding mysterious helps too

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