06/10/2011 06:23 pm ET Updated Dec 06, 2017

The Online Dating Game

I haven't been on a date (except with Phil) in more than 30 years. When I was single, I met many of my dates through friends and family but mostly through work. Apparently nobody's doing that anymore - it seems now that if you're serious about wanting to meet someone, you turn to the Internet. In fact, one stat I read claims that 30 percent of baby boomers are single, and many of them are using online services to find dates. Amazing!

I've been hearing a lot about it lately both the pros and cons - from women who have tried it. I've also heard from friends who are tempted but find the whole concept too strange to even dip their toes in. So with the help of my friends who are in the know, I came up with a guide to help you navigate the new world of electronic dating.

First, a background lesson in how most of these sites work: When you register you will set up a profile with basic information about yourself (age, location, religion, kids/no kids) as well as answer questions about what you're looking for (in those same categories). Then the site "matches" you. Here's a big difference among sites: Some collect only a little information, then show you hundreds of people who meet your criteria. It's up to you to sort through them all and see which ones you'd like to contact. And once you're in that pool, hundreds of people might be looking at your profile, deciding whether or not to contact you. Other sites, however, collect a lot of information from you, then perform a more selective matching service to weed out those who aren't right for you and provide you with fewer, but presumably better, matches. (Most sites also have you write up a free-form biography as well, but the initial matches are made based on the facts and figures in your profile.)

One catch is that the profile information a person provides can be a little deceptive (or more than just a little). People take liberties with their profiles - because they try to anticipate what searchers are looking for. Think about it: You may assume you want a man under 50, but there could be an energetic, youthful 51-year-old out there who would be a great match for you. If you set your requirements to "men, 40–49" you'll never find him. He knows that too, so he may fudge his profile and say he's 49 so that he'll show up as a match for women like you. Same thing goes for you - if you're honest and say you're 51, you'll never get in front of men who want to select from women in their 40s. So take profile information with a grain of salt...or a clump (keep in mind that the "energetic, youthful 51-year-old" man is not the only one claiming to be 49 — you're also likely to find some men in your results who haven't seen 50 in a while!).

With that background info in mind, here are some girlfriend-tested rules for finding love online:

1. Try before you buy. There are two categories of online dating services out there — free sites and paid ones. Most of the women I talked to told me that the paid ones are more worthwhile, and that they had tried one or two free ones first. A free service lets you practice a bit first before committing any money to the process, which can be a good thing. (Friends mentioned OkCupid.com and PlentyofFish.com as examples of free sites — there are others, but these two were brought up the most.) The women who initially tried the free sites reported that the men there weren't always serious about finding someone. Apparently, "serious" men use the paid sites. One friend summed it up by saying, "People value what they pay for. Women want to know that the guy invested time in this. When we're looking at men on the site, we want to see that they really made an effort." You could consider trying your hand at the free sites first, but when you're ready to pursue online dating more seriously, it may be time to subscribe to sites that charge a a fee, like eHarmony.com or Match.com. (There are hundreds of sites and personals out there — these are just the best known among the women I talked to.)

2. To be or not to be...honest. My friends are split on this issue. Some say it's okay to lie about your age in your profile so that you're more likely to be found by those people you want finding you. (See above about being deceptive.) But they say that if you do that, you should come clean in your written biography section ("Just turned the big 5-0!"). Other friends are sticklers for the truth. So it's up to you and the image you want to put out there — testing both approaches on those free sites may give you some idea about what's right for you. One point that everyone I spoke to agreed on was that you must be honest about the big things, and you must be honest in the longer biography — it's one thing to nudge your age up or down a few years in your profile, but there's no hiding the kids, or the divorce, or anything else that's core to who you are.

3. Know what you're looking for — and who's looking for you. One of my friends, who is 42, told me she originally posted her "interested in" age as 42–48, but she wasn't hearing from any men. So she raised the age limit to "53–57" and has been getting two to three responses a day. Her conclusion: "Men my own age aren't interested. But men in the decade above my age range are. They're interested in women eight to 10 years younger.

4. Pick the right site, not just any site. What's the best site for online dating? Sorry, but there's no one-site-fits-all. I have friends who have success and disaster stories from every site out there. So the only way to find out which works best for you is to try them yourself. One friend recently got back into the online dating scene after being out of it for a few years. She says, "I now like sites like eHarmony.com and Chemistry.com because the sites I used to use (such as Match.com) were like meat markets. You'd fill in your form with what you're looking for, then get this giant list of 'compatible' men to wade through. With eHarmony and Chemistry, you fill out this form that's more like a personality test, and the site sends you back three prospects or so a day." Other friends swear by affinity-style dating sites - those that specialize in specific religions or political affiliations, for example. They're just another way to home in on the right match. One friend said, "I know women who routinely go on Jewish dating sites, like JDate.com, even if they're not Jewish — because that's who they want to find — they think Jewish men are really nice."

5. What you see is not always what you get.Profile stats are not the only things that can deceive you. The profile photo, for example, may not be the most current - or may not even be the right person! (Surprise, there's dishonesty on the Internet!) Remember that when you post your own photo, too — of course you want it to be flattering, but it should be recent, and it should look like you (so no major retouching). A yearbook photo of someone decades out of school isn't cute — it's a red flag that the person has no confidence in how he or she looks today. Plus, face it, photos are important; you really do want to know what someone looks like. One friend said that "people lie when they say they don't look at the pictures first — that first they read the profile. Everyone looks at the pictures first."

6. Be skeptical. See above! Besides age and profile photos, descriptive details like height, weight, and salary are all subject to "fudging" in profiles. It also helps to read bios as if you were reading a real-estate ad, where "cozy" means "impossibly cramped." If it's important to you that your guy be in great shape, watch out for phrases like "more to love." It's best to take everything in the profile with a heavy dose of skepticism, and use your intuition: Guys who make $250,000 a year are rarely on free sites.

7. Be safe. I don't have to say this, do I? Email, text, and talk on the phone first to start to get to know each other; don't give out personal information to virtual strangers (no pun intended); and meet in public places until you're sure he's trustworthy.

8. Be realistic. The anonymity of being online makes it very easy to reject someone out of hand. Take a deep breath and be realistic in your expectations. Not every man on the planet is George Clooney, okay? Don't set yourself up to fail.

Whatever site you do decide to take a chance on, do give it an honest try. Don't only partially set up a profile, one that doesn't even have a picture, and then wonder why nobody is contacting you. Wink, email, and talk to a lot of people. And let me know what happens — share your experiences by adding comments below.
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