Online Dating: The 4 Tools You Need to Get Started

by Michael on July 13, 2010 · 0 comments

What the heck, have a second glass. (Photo by SuperFantastic)

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

Are you ready to take the online dating plunge? This post starts a new series on how to go about finding that special girl on the Internet, from finding the best site to taking a killer photo to sending that first e-mail. Today we’ll start off with the basic tools you’ll need to be successful online.

A Very Brief History

Dating (or just hooking up) on the Internet is about as old as the Internet itself. Usenet had “alt.personals,” which were like the personal ads that used to run in newspapers. started as a dial-up dating service in the ’80s. started in 1995, and hundreds of other sites sprung up, disappeared, and were absorbed by larger sites (Match alone has consumed the likes of, and now Yahoo! Personals).

Today online dating has reached maturity: major sites like and eHarmony have become entrenched by outlasting and buying their rivals, and newer free sites like Plenty of Fish and OKCupid are capturing those who can’t afford a monthly fee. Each site has its pluses, minuses and a different kind of clientele. We’ll look at the various options in the next post of this series.

My Story

I tried online dating for the first time in around 2000, and virtually all of my girlfriends for the next few years were women I met online. It was an interesting variety of women, each with a different story and none of whom I would have met if I hadn’t gone online. I dated a society-connected executive, a designer fashion model, a traveling saleswoman and a starving artist. Propositions I didn’t accept included a masochistic polyamorist, a lesbian couple looking for their first experience with a man, and someone who informed me (when I suggested I’d like to see a photo) that she didn’t care if I “looked like a troll,” which kind of made me wonder if she looked like a troll.

Subsequently, I learned the skills to meet women face-to-face, which enabled me to skip the e-mails and out-of-date photos and get right to the dating. However, Internet dating has its place, and if you do it right, it can be an efficient way to meet women.

What You Need

Most guys find a couple of old photos, list a bunch of the things they like to do, and wonder why they can’t convince anyone to talk to them. Would you walk up to a woman on the street and tell her, “I love fishing and football—Go Hawgs!—and I change my own oil, and the hot wings at Buff’s Wings RULE”? No, you’d give her something interesting to react to.

Here are some of the tools you’ll need to really shine online:

  1. A little creativity. An online dating profile is an ad for you. So is your first message to that girl with the awesome photo. You’re selling yourself, so do it well. A list of things you like makes you look boring, no matter what’s in that list. Ditto with a canned e-mail you send to multiple women: they can tell it isn’t a personal response. If you need creative help, enlist a friend.
  2. Willingness to experiment. If what you’re doing isn’t working, it doesn’t mean you suck or the women are lame, it means you’re doing something wrong. If you’re not attracting the kind of women you want, you may not be speaking to those women. Be willing to test and change your approach. You’re a multidimensional human being—try showing another dimension.
  3. Real-life dating skills. Unless you’ve decided to be a hermit and only deal to women on the computer, you’ll eventually have to meet them in person. At that point you’ll have to be able to hold a conversation, interpret her signals, and know how to start and end a date right. So it’s a good idea to continue meeting women in “real life,” honing your skills so that you can easily slide between the online and flesh-based world.
  4. A positive attitude. Probably more than any other trait, a bad attitude sticks out like a sore thumb online. Nothing will shut a woman down faster online than anger or impatience, or in many cases even sarcasm. If you’re hating life, step away from the keyboard and come back when you’re better. Online dating always holds an element of the unknown, and if you don’t really care for adventure, it might not be for you.

In the next post of this series, we’ll review dating sites and find the right one for you.

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