Just as with dating, online matchmaking sites must attract potential suitors (and suit-ees), court them and woo them into long-term relationships.

It’s two days before Valentine’s Day and singles everywhere are hustling to round up dates.

Indeed, 85 percent of singles across the country who responded to a Yahoo! Personals survey admit that celebrating Valentine’s Day is important to them. And according to data collected from Yahoo’s “Project: Real Valentines,”—a campaign launched this to week to encourage singles to create profiles and be chosen for a special date paid for by Yahoo—83 percent of single men and women are willing to go on a first date with someone on February 14th.

Where are they going to find those dates? Increasingly, it’s online dating sites like Yahoo’s, the fastest growing segment of the Internet.

Last year, online singles communities brought in more revenue than any other form of legitimate paid Web content. Having grown 37 percent in 2003 to a $313 million market, the online dating industry has the potential to eclipse, rather than merely complement, traditional dating services and techniques.

Membership quantity is the measure of success for dating service executives as well as for consumers—the more members there are to choose from, the better the odds of finding a soul mate. But volatility plagues the industry; over the past six months, four sites have been at the No. 1 market share position. Thus, marketing and advertising are having to serve larger roles for defining differentiation. The most successful sites are learning to use more realistic creative and a targeted direct approach to increase traffic and improve conversion rates.

Without a dating reference tool such as Ellen Fein and Sherrie Schneider’s infamous book “The Rules” to clearly define how to win someone over, businesses are forced to learn as they go. Perhaps understanding the strategies and results of recent matchmaking campaigns can teach e-marketers how to capture the right, or rather ‘Mr. Right’s,’ attention.

First Things First: Sell the Medium

As marketers sketch the messages they will employ to captivate social audiences, their first point of conflict involves rationalizing the online medium to skeptics.

"We did a lot of consumer research and found out that while we've done a great job of legitimizing the category, we still hear people say `I think it makes sense, but it's not for me,' " says Melanie Angermann, vice president of marketing for Match.com. "And we decided that instead of dancing around it, we'd attack it head-on in our new advertising."

Others, however, demand that the stigma is almost gone, especially among youth who more readily embrace communication via the Internet. Tickle, a site that fuses matchmaking and networking services with tests and quizzes, has found that the same people who were worried about putting personal information online just a few years ago are now happily filling out profiles.

As traditional consumers are now hearing more and more anecdotes about friends or colleagues meeting someone special online, they are becoming a more captive audience. But this audience is complex, and the growth of several niches is creating new opportunities.

Being All Things to All People Spurs Failure

Direct marketing is most effective when the content of the message is designed specifically with a target in mind. Email campaigns and contextual marketing are proving to be the top leaders of delivering a solid ROI for online dating companies. However, some sites continue to attempt to appeal to the mass market.

“Incumbent dating sites experiencing decreasing market share are realizing they are not targeting their messages effectively enough,” says Michael Rice, CEO of Citrus, a brand response agency for e-commerce companies. “Their investments would be more cost-effective if they used agency research tools to profile customers and find exactly where they are located online.”

Instantchem.com, for example, understands that it must market the quality, not quantity, of members to its post graduate school target. Similarly, eHarmony maintains a precise focus on adult singles, especially Christian singles, who are looking for a long-term relationship. Because of this niche, email marketing as an introduction to a service presents more of a challenge. Using purchased lists has not delivered attractive conversion rates for the Pasadena-based company, whose average customer skews older than that of mainstream dating services like Match.com.

“We no longer do large CPM deals, but instead use email for loyalty,” says Steve Hartmann, online manager at eHarmony. “The majority of our customers have tried another dating service and not been pleased.”

In its advertising online as well as in radio and on television, eHarmony is using a real-life portrayal of active members to attract new ones. There is no doubt the company’s campaign, featuring actual couples who met using eHarmony.com and are now either married or engaged, stirs up an emotional connection in consumers. The company’s membership has quadrupled in size since January 2003 and currently averages more than 10,000 new users a day.

Truth in Advertising Pays Off

While valuable, eHarmony’s strategy is not unique. Yahoo! Personals also launched its "Project: Real People" ad campaign last month, with executions online and offline (a Sunset Strip billboard in Los Angeles). The multimillion-dollar campaign used live video feeds to give consumers a peek into a real-life member's dates. Other creative featured average-looking members in banner ads on Yahoo! and iVillage that read "Models? What models? We're all about real people."

This call to mainstream America takes advantage of those singles looking for a welcoming and less intimidating environment for their online dating experience. Known for a tongue-in-cheek advertising style, Yahoo! Personals currently boasts the leading market share at 18.23 percent, according to Hitwise.

Vanity Date, ironically, also sells itself through a ‘real’ approach. The company utilizes honesty and bluntness with a tagline "Survival of the Prettiest." The statement so aggressively rejects ‘Average Joes’ that members are reassured they will only be connected with equally attractive singles. Not only does Vanity Date admit to being "the world's most judgmental, shallow dating Web site,” it even allows members to vote on whether or not to accept applicants. Is an NBC “Vanity Date Survivor” reality series in the works? Let’s hope not.

Be Aggressive While Playing the Field

MatchNet, which manages AmericanSingles, CollegeLuv, JDate and a slew of other sites, dominates lucrative niche markets but lately has been feeling pressure to defend its user bases.

“We have become more aggressive in trying to retain subscribers by utilizing internal email marketing,” says Gail Laguna, vice president of communications at MatchNet. For example, the company is using 'value ads’ and retention in various email campaigns. The former is intended to convert free members into paying members by offering promotions at partners like Bally’s Crunch Fitness. The latter, called the 'Save' program, offers discounts to Premium Members who attempt to cancel their subscription. The program has improved the lifetime value of the customer as well as resulted in improved retention rates.

Effectiveness, not the mere size, of email campaigns is what’s truly important to marketers in the end. MatchNet’s Laguna agrees: “No campaign is too small or too big for AmericanSingles. We just make sure the conversion is there for every campaign, regardless of its size.”

Though an email campaign is an inexpensive tool that generates immediate response, it should be thoughtful and reserved, not abrasive and over-eager. Body language is key. Like a gentleman would treat his date’s mother with respect, so too should direct marketers. The trick to the first email is to make it quick and painless; just ask for limited information (e.g. first name, last name, email address) to start because subscribers are more likely to complete a short form than a longer one at the beginning of a relationship.

Once consumers sign up for paid services, how can brands keep them loyal?

Make Customers Attached at the Hip

Just as in any romantic relationship, there comes a time for online dating marketers to engage in a "define the relationship talk” with customers. An exchange of expectations, needs and feedback are crucial to ensuring long-term commitment and compatibility. For example, placing a privacy policy at the bottom of a landing page or email lets subscribers understand how their email address will be used.

Like its content suggests, online dating customer loyalty is a courtship. It requires nurturing and constant communication. Matchmaking services face a unique loyalty challenge primarily because once a member finds a significant other, he or she tends not to use the service anymore, and thus terminates the membership.

Retention email is an important tool for Tickle’s matchmaking and test subscription businesses. The emails communicate with users over a wide variety of topics: showing them compatible people to consider dating, showing them new people who have joined the matchmaking service, reminding people to check their premium test results, auto-sending birthday reminders, and more.

“We've found that offering compelling content is the best way to create loyalty, and with over 250 tests and quizzes to choose from and great user-generated content in the Matchmaking and Social Network realms, we keep people coming back without having to offer them some kind of pseudo-financial incentive,” says Steven Comfort, Tickle’s vice president of Sales and Marketing. That explains Tickle’s frequent blast of newsletters aimed at focusing users' attention on new products, features and tests.

In the end, remember that social consumers require an emotional connection. Joseph Newton once said, “People are lonely because they build walls instead of bridges.” Sell the “bridge” and success will follow.

Rebecca Weeks currently directs Strategic Marketing at Citrus, an interactive brand response agency in Los Angeles. She is known for her exceptional industry analysis and trend-spotting skills.