Online Dating: Words Matter

by Michael on September 15, 2009 · 0 comments

If only he could find the words to describe her beauty... (Photo by Don Hankins)

If only he could find the words to describe her beauty... (Photo by Don Hankins)

Update: The Tao of Bachelorhood Guide to Online Dating, based on this series but revised for the Kindle, is available on Other versions to come. For a limited time it’s only $1.99!

I’m a big fan of meeting women out in the real world, but I’d be lying if I said I never tested the online dating waters. And yes, it’s a time-sucking black hole full of old photographs and rampant fibs about weight and age. Still, in a relatively short time I managed to share some great adventures with a number of women I’d have never met otherwise. (And was offered still more adventures by women I wasn’t so sure I wanted to meet.)

But if you’re using a dating site now, I want to help you with a critical part of the online dating process: the contact e-mail.

You may not be a great writer. Your longest recent compositions might have been the size of a Tweet or text message. But that’s okay, as long as you keep some basic rules in mind:

No Canned Replies

The first impulse when you’ve just signed up for or Plenty of Fish might be to pull together a generic note that you’ll send to every woman who catches your eye. Stop right there. No matter what you throw into it, a canned reply demonstrates that you haven’t read her profile — and she will feel perfectly fine deleting your message and moving on to the next 100 canned replies.

You might think that just sending “whassup” shows you’re cool and calm, but half the guys online are doing the exact same thing. Actually mentioning something about her will make your response stand out. Remember, women on dating sites are slammed with responses, so you want to let her know you’re the one who actually knows a little about her.

Now, you don’t have to compose your entire message from scratch. I would sometimes find an interesting opener regarding a great place I’ve been. One evening I was writing responses from my favorite coffee shop with a view of the beach, right at sunset. So I used that in my initial greeting to the women I contacted that evening, before I asked a few questions based on their profiles. Don’t be scared to be a little poetic or playful.

Ask Questions

You don’t need to make your response about you at all — she’ll get all that from your online profile. Instead, ask her questions. Ask about her hobby, or favorite food. Quiz her on which movie she saw last weekend. Inquire about her pet. Although you should ask her primarily about things you learned from reading her profile, although you can also toss in a fun general question or two (“what’s more likely to be your guilty pleasure: Abba or Kiss?”). If you’re going to say anything about yourself, it should be something not in your profile, and it should relate to something about her.

Write Right

You may refer to your friends as “u,” but you’d better learn how to write out the entire word when you contact online hotties. What’s good for a text message isn’t so good for conversation. This is backed up by science: parsed the text of 500,000 first-contact e-mails sent through their system and tracked how many got responses. People who used “ur” instead of “your” found their e-mails thrown in the trash with no response 95% of the time. Reply rates were similar for “u,” “r,” “ya” and “cant” (without the apostrophe).

Don’t Grovel

If she looks smoking hot in her photo, she doesn’t need to hear it. The OKCupid survey showed that e-mails using “sexy,” “beautiful,” “hot” and “cutie” got fewer replies than average. On the other hand, words that refer more to personality, like “cool” and “fascinating,” got higher reply rates. Again, this is something that shows you actually read her profile, and didn’t just look at the photo (you never know if that photo’s an accurate representation anyway). People who used specific words describing interests got more replies than average.

Have Your Profile Ready

If your e-mails aren’t working, the problem might actually be your profile. Make sure your photos are good: well lit, showing your “good side,” with a smile on your face. Oh, and you may be proud of your six-pack abs, but unless you’re under 30, keep your shirt on in your pics. Then rewrite your profile text. When I was online, I used completely different text on than I did on Then when I determined the text on Date was working better, I changed my Match profile to the same text, and my reply rate skyrocketed. Have an opposite-sex friend read your profile and make suggestions.

There are a lot of other nuances to successful online dating. You’ve got to be good at actual in-person dating to seal the deal, but you can be a love god in person and no one will know it if your e-mails aren’t cutting the mustard. Try different approaches, and be in a good frame of mind when you’re writing — it will show.

For more from OKCupid’s study, head over to Exactly What To Say In A First Message.

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