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Update: Get the entire Online Dating series, updated and compiled into the Tao of Bachelorhood Guide to Online Dating, absolutely free! Just subscribe to Tao of Bachelorhood to the right of this article or on the Subscription page.

Last week we looked at the “Big Three” online dating sites: Match.com, eHarmony and Plenty of Fish. Today we’ll go down a level to sites that aren’t as well-known but offer more places to cast your line. They range from the small and cool to the large and, well, minimal.

To repeat my recommendation from last week, try a few sites to see which one fits your style and offers the best selection, then focus on one site to begin with, branching out to others if your time allows. Use the free trials many paid sites offer, or start with a completely free site like Plenty of Fish or OKCupid. Starting next week I’ll help lead you through the process of writing a great profile, getting your photos up and contacting women.

First, though, let’s round out the top dating sites:

SinglesNet

Monthly cost: $25/mo or $90/yr.

The folks at SinglesNet proudly trumpet “#1 Visited Dating Site!” Then the small print reads, “Dec. 2008.” Last year, though, Forbes put SinglesNet at fifth place, behind True (which I won’t recommend, for reasons I’ll get into later).

I’ve got to say, I’m completely unimpressed with SinglesNet. The first time you go to the site you’ll see an option to search for women in your area. Try it and you’re presented with search results—which you can’t access because they’ve overlaid a sign-up screen. A bait-and-switch like that only sets you up for the disappointment within.

There is no matching technology on SinglesNet that I can see. Searching is extremely simplistic: Age, location, and ethnicity. Age is even approximate: “around my age or younger,” “around my age or older,” “around my age” or “any age.” You’re basically getting a list of random women in an approximate age group, sorted by how long ago they last logged in. If you have the time to manually go through the profiles you could find a catch here, but I wouldn’t see myself paying $8 or more a month to manually sort women.

You’ll also want to shut off all e-mail alerts, because every time someone views your profile you’ll be sent an “interest” message. And the reverse is true: every time you click on a gorgeous face that turns out to have the profile of a career criminal, she’ll get a message that you’re “interested.” There’s very little online help, but with not much to do you probably don’t need it. And be careful to treat the women you meet here right, or they’ll put your handle up on the “scams” message board.

Zoosk

Monthly Cost: $30/mo or $120/yr.

Zoosk has positioned itself as the most social-network friendly of dating sites, and that’s great if you want your Facebook friends to follow along with your online dating exploits. It also allows you to give “gifts” just like Facebook (“Oooh, how sweet, he sent me a picture of flowers!”), and has you earning “coins” that presumably pay for the gifts. Looking and “winking” is free but you have to pay to contact, like most other sites.

Profile information is sketchy: no personality-based matching, and no body type information. Most of your work here will be on the essay questions. But there are a few extras: if you like comparing your Netflix queue or Last.fm playlist you can link to them. Searching for local women can be done using any of the multiple-choice answers and any age range, but there isn’t any matching technology here.

One Zoosk-specific feature might just be money: you can invite your friends to write “testimonials” to talk you up to the ladies. Hit up a couple of your best wingmen and craft testimonials for each other. It can’t hurt (as long as he doesn’t bring up the part about the projectile vomiting last weekend) and can certainly help.

Again, I wasn’t impressed with the selection of women here, compared to Match or Plenty of Fish, but what I did notice is that women on Zoosk seemed much more playful and tuned-in. If that matters to you, give it a try.

OkCupid

Monthly Cost: Free (extra matching features $10/mo)

The OkCupid logo is a beaker, which is your first clue that this site is about science! In fact, in complete opposition to the above two sites which use virtually no matching technology, OkCupid is almost entirely about matching. You could spend weeks on all the questions and tests that get you just a little more finely-adjusted matches.

Not to mention it’s fun to find out more about yourself, and explore the various traits of women you’re interested in. See if she’s earned the “More Kinky” badge, or find out her “Lover Style.” You can search on a number of criteria, but matching is always at the heart of OkCupid. You can improve matches by answering more “matching questions,” about everything from politics to TV shows to your fingernail-grooming habits. OkCupid also tracks (anonymously) the habits of its users and also does independent testing, and can tell you that those shirtless photos do work.

Best of all, it’s all free. Okay, nothing in life is really free – OkCupid makes its money selling something called the “A-List Subscription.” This gives you more search features (sort profiles by personality traits or popularity), messaging features (attachments) and visibility (“A-List” profiles appear in a special section on search pages—this would seem to defeat the point of matching, but whatever). Also, paid users don’t see ads, although they’re already the least intrusive of any site.

Since basic matching and contacts are free, you’ve got nothing to lose.

The Others

There are dozens, maybe hundreds of other places to find an Internet mate, from the simple-but-free DateHookup.com to the “intimate dating” site Mate1.com to ethnic- and religion-specific sites like BlackPeopleMeet or JDate. Match started up Chemistry.com to win some of the personality-match market from eHarmony. Some long-time standbys like Lavalife and Date.com still exist. If you have the time, check a few out.

There’s only one site I’ve had trouble with: True. Billed as the “safe” dating site, they certainly offer a number of matching options. However, the price to contact other users is prohibitive ($50/mo or $130/yr). And what’s more, the “safety” apparently ends outside the walls of True, as I was relentlessly spammed by them. I couldn’t turn it off. I tried sending them e-mail but it didn’t gain a response. I had to take the radical step of training my e-mail provider to treat them as spam. I’d like to go back there and check them out for you but I just won’t take the chance again.

And Then There’s Craigslist

If Craigslist is the Internet version of want ads, their personals are the Internet version of alternative-weekly personal ads. The people you meet will be a mixed bag, and there’s no searching or matching. Just either write up an ad or go look through the “Women Seeking Men.” The beauty of Craigslist is that no matter what you’re looking for, you just might find it. The downside is that you might find a lot of what you don’t want as well.

I could do an entire series on using Craigslist personals, and I just might, but for now let’s stick with some structure.

Your mission is to try a site or two. Sign up for free and explore, and let me know what you like or don’t like about the sites you check out.

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Update: Get the entire Online Dating series, updated and compiled into the Tao of Bachelorhood Guide to Online Dating, absolutely free! Just subscribe to Tao of Bachelorhood to the right of this article or on the Subscription page.

Today online dating has reached maturity: major sites like Match.com 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.

I recommend that you try a few services. Most have a free trial offer of anywhere from a week to a month—if you’re efficient and apply yourself you might generate a number of “real life” dates within the trial itself. Make sure you’re making an appropriate effort to create a quality profile and respond well to the women who catch your eye. (I’ll cover that soon.)

First let’s look at the Big Three competitors, which will feature the broadest range of women to choose from. Later we’ll go over some of the smaller or alternative options.

Match.com

Until about a week ago, Match was third behind eHarmony and Yahoo Personals in total users. However, Yahoo Personals merged with Match, in theory adding their millions of users to Match’s millions to create an Internet dating goliath.

I say “in theory” because let’s face it, Yahoo Personals was made up of a ton of inactive free accounts. Searching for active users who could actually respond to your messages was incredibly hit-and-miss. The number of actual paid Yahoo users moving over to paid Match.com accounts could be anywhere from 50,000 to half a million—most dating sites don’t like to give away their paid-subscriber numbers because they’re far below the combination of paid members and free “looky-loos.”

But back to Match. This is the gold standard of paid sites, and they work hard to keep improving their offering. They’ve come a long way since I used their services several years ago. In addition to their powerful search function and contact tools, they offer the “Daily 5,” five women their software determines closely match your profile, and an in-house service to improve your profile (at an extra charge). They’ve also created chemistry.com to compete more directly with eHarmony. I like the fact that I can search for exactly what I’m looking for, including body type.

The downside is that you’ll have a lot of competition here—more people means many more guys who think they should send a form e-mail to the same 5% of the women. If you can stand out (and I’ll help you there), you can succeed, though. I did.

eHarmony

You’ve seen the ads with the happy married couples who met on eHarmony. You’ve heard about the “29 dimensions of compatibility.” You may even know that before the Match takeover of Yahoo’s customer base, eHarmony was the largest dating site in the world. Forget them. There are two things you need to know before you fish in the eHarmony waters: the Big Plus and the Big Minus.

The Big Plus for eHarmony is that about 60% of those millions of users are female. That’s right, the best odds online are at eHarmony. You’re outnumbered almost 2-to-1. Two girls for every boy, just like Surf City. In contrast, Match is almost even in male-female ratio, and Plenty of Fish has a slight lean towards more men.

But that brings us to the Big Minus: you don’t get to choose the women you can contact. No searches for “slender, blonde hair, with the keyword ‘MMA’ in their profiles.” eHarmony chooses the women for you, based on those 29 dimensions. You can tell them to filter for smoking, drinking, children, age, religion, ethnicity, education, income and distance, but after that it’s up to their computer algorithm.

After you’ve completed the personality tests and lists of “values,” eHarmony will start sending you profiles of women who they believe are a match. You can decide which to contact, and they try to make it fairly easy, even offering an anonymous phone forwarding service so women feel secure talking to you. All of this may actually save you from yourself if you don’t want to put a ton of work into online dating, but it may be a jolt to see the women you “match” if you’ve been overvaluing yourself on other sites.

Plenty of Fish

The number one great thing about Plenty of Fish (or plentyoffish) is that it’s free. And it used to be completely free, but last year the site started offering a paid upgrade option to push your profile to the top of search results. The gimmick is that upgrades are only for those “serious members” looking for relationships. There’s a short test you must take—and quite frankly it’s probably easy to guess the “right” answers, so I don’t see it stopping anyone—before you’re offered the chance to pay between $6-10 per month.

My advice is to try the free service for a while first and see its strengths and weaknesses. Plenty of Fish is strong on numbers, so there are millions of women with profiles. Unfortunately, the site is weak on matching, so to find appropriate women to message you’ll have to use the Search feature and enter your criteria. Fortunately, the site remembers your last search so that you can repeat it to find new members at regular intervals.

Best of all, it’s free to send a message to any woman who floats your boat. However, members are allowed to specify who may send them messages. Most require a picture. Others will only allow you to talk to them if you don’t smoke. And it’s a dwindling few who will accept contact if you’re looking for an “intimate encounter.” (That means sex. Just thought I’d make that clear.) If your profile meets her criteria, though, send that note and get the party started!

The interface is clunky and it’s hard to find all the various controls, but if you can master it Plenty of Fish should be a great option for the cash-strapped. (Just don’t tell her you’re cash-strapped.)

Plenty of Sites

These are simply the largest sites out there, but there are many more worth your while for different reasons. In Part 2 we’ll look at OKCupid, Craigslist and specialty sites, as well as one or two you might stay away from. Until then, sign up for free at one or more of the “big three,” and take a look around.

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