Recently I was e-mailed, via Match.com, by an attractive woman (to the extent that profile pictures can be trusted, anyway) named Kathleen. I love that name, and her profile made her sound like someone I’d be interested in talking to a bit more, so I replied. We exchanged a couple of e-mails and I was thinking that maybe I’d like to meet her in person.

Then she asked me if I liked skiing. I answered honestly. I love skiing, although I’m not great at it and I haven’t been on the hill since I annihilated my knees a few years back. I’d love to get back into it, though, but haven’t so far because I hate doing things alone.

I knew as I hit the send button that I’d never hear from her again.

I’ve been a Match member on and off for maybe a year and a half and have very little nothing to show for it. I tried to play it straight, using my profile to tell the wonderful women of the 5280 who I was as best I could – what I do for a living, what I do for fun, what my interests are, and so forth. But no results to speak of past a few coffee first dates. Whatever I served up, nobody was buying.

I don’t mind admitting that it’s been frustrating. And yes, it strikes at your self-esteem. I have historically hit periods when, as a result of where I lived or the structure of my daily life, I had a hard time meeting women, but I’ve never had trouble getting dates when I was actually around eligible women. My Match.com experience, though, has begun to make me feel like an untouchable.

I’ve had plenty of time to think about what the problem might be, and a good deal of that energy focused on the perfectly valid question of “what’s wrong with me?” Back when I was more successful on the relationship scene I was, after all, a bit younger, and I’ve had to entertain the uncomfortable possibility that 50 year-old Sam is simply less marketable than 30 year-old Sam.

I concluded that the problem is multi-faceted. For one thing, I’m just not Outdoorsy Guy, but I live in the middle of Outdoorsy Nation. Also, I’m picky as hell (when you’re educated to the doctoral level, for instance, you’re going to be looking for someone with significant intelligence). And there are plenty of things about me guaranteed to cause daily match surfers to lunge for the “next” button – as in, we know that a substantial percentage of American women don’t find bald guys attractive, period. I get it. Since there’s nothing I can do about some of these things (short of leaving Denver and joining Hair Club), I decided to go straight at the issue as best I could. So about three weeks ago I changed my profile. Here’s how I began:

The great thing about Match is the chance to meet women I might never encounter otherwise. The bad thing is that somehow the place encourages us to define ourselves as a checklist of things we like to do. Shared interests and compatibility are nice, but I’ve always felt like relationships thrive on a chemistry that has very little to do with activities.

The working theory for businesses like Match and eHarmony, I suppose, is that true love is best predicted by that checklist of activities. (eHarmony may not be as bad about this as Match – I have no experience with them past filling out the application form.) You like live music? You’re the oldest child, too? We’re soulmates!

Then, yesterday, I tripped across an interesting new study headed up by Dr. Eli Finkel, a Social Psych professor at Northwestern. Finkel’s team agrees that online dating is a great way to discover people you might not meet otherwise. However:

One of the weaknesses of online dating is an overreliance on “profiles,” the researchers say. Although most dating websites feature photos and detailed, searchable profiles covering everything from personality traits to likes and dislikes, this information isn’t necessarily useful in identifying a partner, Finkel and his coauthors write.

The study suggests something that I think most of us know, even if we’ve never stopped to think about it. To wit, love is often about serendipity.

…daters don’t always know what they want in a mate—even though they generally think they do. Studies suggest that people often lack insight into what attracts them to others (and why), and therefore the characteristics they seek out in an online profile may be very different from those that will create a connection in person, the review notes.

Fight it if you like, but Marshall McLuhan’s adage applies to online dating: the medium is the message. In a format that emphasizes “things I like to do” and sorts according to activities, your viability is going to hinge on how well you conform your life to those dictates. Is the “shared interests” assumption valid? Well, it’s obviously nice if the person you’re interested in likes some of the things you do. If you have nothing in common the relationship probably has a short shelf life. But let’s be honest. There are probably lots of people out there who share nearly all my interests that I’d think are barking assholes. Some of the most compelling women I have ever met, on the other hand, had very little in common with me….at first.

See, if the click is there, people find things to do. They grow together. They shape their world to fit the emotional, spiritual and physical connection instead of robotically sorting themselves according to somebody else’s preconceived generic categories. She grows to enjoy watching games with him. He realizes how much he likes watching movies with her, even movies he wouldn’t have been caught dead watching before. She’s never had any interest in going to New Mexico until she spends a weekend in Taos with him but now she can’t wait to go back. He always thought of sushi as bait until she took him to the Sushi Den and eased him into it with a California Roll. Now he’s badgering her to go check out this new place called “Sasa” he heard about up in LoHi.

When you interpret who you are and what you have to offer another human being according to a mass market dating corporation’s categorization schemes, you place significant limitations on what you can be and on who you can discover. Homogeneity is bound to be the result.

My friends have heard me complain about this templating tendency and about the seeming sameness of the single women in town. If you believe what you see on Match 99% of single females here fall into one of two or three categories (if that). I joke that between the time they spend camping, hiking, skiing, climbing 14ers, mountain biking, laying on the beach in Mexico and volunteering with poor children in either Africa or Chile there’s simply no time left for them to actually be in Denver. They’re all in love with their careers and have great friends. Family is incredibly important to them and if they don’t have children of their own they’re okay with it if you do because they love children. At least two pictures of their dog(s). And so on.

I was deep into this rant with my buddy Mike a few months back and he was laughing at me, so I logged in and called up my daily matches to prove it. The first profile was a little off. The second was word for word, picture for picture what I just described.

I noted above that I feel a lot of frustration with the process. I try to be honest about myself. I’m 51, which means that statistically speaking I’m playing the back nine of life. I’m not a runway model. I have no hair. Like just about everybody who has lived past the age of 12 I’m broken down in some ways, both physically and emotionally. Yes, I have baggage.

That said, talk to my female friends. I’m a pretty good guy. I’m not David Beckham, no, but I’m okay looking. If you saw pictures of all the beautiful women who have been a part of my life through the years you’d have to conclude that I must got something going on. I’m smart. I’m creative. Strong and sensitive in fairly equal measures. Funny, thoughtful. As for the baggage, most of it fits in the overhead bin.

In other words, I’m not a bad catch.

But: all those gorgeous women who loved me? Almost none of them loved me on sight. Some of them disliked me at first, in fact, and others didn’t warm up to me for quite some time. I understand all this. The things that are best about me simply aren’t evident at a glance. And there is no way to communicate this dynamic in a Match.com profile. (Or speed dating environments, either, for that matter.) In an online dating context you can’t make me look terribly desirable to the female window shopper without lying.

I have no doubt in my mind that dozens of women who might like me a great deal if they knew me have zipped past my profile without a second thought.

If I sound narcissistic or self-indulgent here, stick with me for a second, because this is a sword that cuts both ways. In short, I’m guilty, too. Here’s how the story on the Finkel study concludes:

The abundance of profiles online also may make daters too picky and judgmental, the authors say. The sheer number of options can be overwhelming, and the ease with which people can sift through profiles—and click on to the next one—may lead them to “objectify” potential partners and compare them like so many pairs of shoes.

“Online dating creates a shopping mentality, and that is probably not a particularly good way to go about choosing a mate,” says Harry Reis, Ph.D., one of the review’s authors and a professor of psychology at the University of Rochester Medical Center, in Rochester, N.Y.

The shopping mindset may be efficient online, but when carried into face-to-face interactions it can make daters overly critical and discourage “fluid, spontaneous interaction” in what is already a charged and potentially awkward situation, Reis and his coauthors write.

How often do I find myself in that shopping mode? How often does it become about reflexively saying no instead finding a reason to say yes? I just took a quick break to review my daily matches, which refreshed as I was writing. Seven women, and I cleared the list in less than 30 seconds.

How many times in the past six months have I looked at a picture of a woman who would make me insanely happy for the rest of my life and clicked no? No telling. I do know, from personal experience, that there are women I don’t think are attractive or interesting when I first encounter them, only to later conclude that they’re stunningly compelling. (I have a friend like that in my life right now.) I’d be stupid to assume that doesn’t happen routinely on Match, wouldn’t I?

Thanks for the memories, online dating, but I’m signing off as soon as my current subscription expires. Your system may work great for some folks, but the more I think about it the more I realize how perfectly it’s engineered to fail for me. My perfect match and I are going to walk right past each other without even noticing 100 times out of 100.

And I just don’t want to be that guy. You know, the one who bitches because women don’t give him a chance while he’s not giving them a chance? You’re making me a worse person. Or rather, I’m using you to make myself a worse person, and it has to stop.

I may not find anyone at all. Who knows? But at least I can stop shelling out $30 a month for the privilege of deluding myself.