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Online Dating- The Perils, The Pitfalls, and The Prize

Updated on May 30, 2012

Six months after separating from a 13 year Marriage with two small children, I got the bug to see what online dating was all about. Like most of the middle-aged married folk, my limited exposure prior to signing up was stories from a few single friends. It sounded like fun...I had an idea I would be "good at it", but here I am, three years later, over 175 dates, still in search of something even resembling a "significant other". "How's that possible", you may be wondering? Am I the pickiest guy ever? Is mutual chemistry on a date as illusive as a World Series Win for the Cubs??? Read this blog, and decide for yourself....If nothing else, it will be entertaining.

What's your AGEnda?

I lied about my age, at first. It was a big lie, and I knew there was a risk. But 5 years should not have been a big deal, right? I could easily pass for 5 years younger. I knew it would not be easy to go out with women in their late 30's or early 40's if I told the world I was in my early 50's?

Since I had some very well-established predilection for this age bracket, the risk seemed to outweigh the rewards. In searching through thousands and thousands of photos, I would say that I am physically attracted to almost 10% of the women I see under 40 and probably 1% over 50. Unfortunately, my plan backfired, and I don't really recommend it.

Many women- not all- see the Male Age Lie as the TOTAL- I can never ever trust you on anything- SORT OF LIE. There is nothing white or slight about it. Apparently, if you LIE about your age online, even if you look pretty damn good for it, women just assume that you will lie someday about other women, how many children you really have, what you do for a living and what you make, etc., etc.

If you do want to go with the "lying age" routine, however, I would recommend the following:

1) Be good at Math- and have a great Memory- You need to add 5 years not only to your DOB, but also to the music you liked, what you were doing when, the people you liked in school and hung out with, etc., etc. As a reformed horrific liar, I find this has taken some of the pressure off the whole dating experience.

2) Be good at lying- Some of us are; some of us are not. I'm not passing judgement here, just stating a fact. Good liars can carry this out for decades without getting caught, if need be. It's a lot of work, but they do it seamlessly.

3) No reason to lie at all if you like women your age or older- You are a lucky dog. Trust me, I have tried, and keep trying, but it's easier said than done for me.

4) Change the subject. "No, really, how old are you, and why are you afraid to tell me....are you older than my Dad?" You cannot turn red at this point, unless you are eating spicy, and then, it could actually work out well...keep chowing down the spicy and she may ease up on the age inquisition. Always be prepared- Always have a more compelling subject to divert her attention.

Big pain in the ass, right? So, I guess getting theoretically more responses from a 38 year old by dropping down to 49 was going to be worth it. It wasn't too terrible until I waited until the third date on someone I really (finally) liked, and she completely flipped out on me with the whole patented "if you lie about your age, you will lie about anything" routine... And it was just over; no turning back; no talking her out of it.

If you are trying to be all about "trust and honesty" and you are dishonest about your age, you cannot win here. If you look good for your age and want to play the game to the max, you have far less to gain and far less to lose. One of the many things I do not understand here is that I doubt the nicest, most honest guy who is attracted to a woman, who is genuinely attracted back, would be extremely pissed off at a woman for an age fib. It is but one of many double standards one encounters when dating in today's world.

First Break in Three Years

I never understood why Online Daters needed to take a "break" from Web-Mating....until I took one myself. Perhaps my incredulity was based on the propensity of lies women told me as to why they were not going out.... and "the break" was foremost in the repertoire of why they decided to blow off a date.

I still believe it was a bogus excuse most of the time, but since my friends were typically going on and off of online dating sites, I recognized it was not always a poor excuse for not meeting someone. I was fairly sick the past two months, and simply could not participate in the obsessive activity with the usual vim and vigor. Now, I did not take my photos or profile down, and I certainly checked email often enough to know if any Natalie Portman look-a-like was pining for me. However, this doesn't really happen to guys, and I would venture to guess, it does not even happy to Hot Young Ever Abbed guys. We males are still the PURSUERS, for the most part. AND, most of the time when we are the objects of pursuit, instead, it is from the type or look of women that we would have chosen not to pursue in the first place.

I am still laying back as I recover from my illness and I am really in no rush to return. Online dating was an obsessive game for me. I was not addicted to the game of "sleep with as many women as possible"....I was just convinced that a suitable partner was out there, and I was going to search, IM, email, and dedicate myself an hour or two a day or possibly even three or four. I found this challenging and enjoyable, even as I found it frustrating meeting so many, and liking or being attracted to so few.

Many components of "addiction" were there. I needed to go to the site frequently; needed to respond quickly to the few women who I was interested in that responded to me; needed to see what was "out there" that I may have somehow missed. Others advised me to give it a rest- but I looked at that as "quitting".... etc., etc.....it all adds up to "addiction" . I just did not want to see it.

I don't know that I've sworn off dating sites for good- because that is not the point. It's been a fairly challenging time in my life, and I know that dating, particularly online dating, requires that one is on top of one's game. It's no secret that men, in particular, will find it far easier to get through the process with quality encounters of the opposite sex if their financial life is well under control. It was an extremely burdensome problem for me. I am just glad to lift that burden, because making tons of money in this economy is challenging enough.

I needed a break. Anyone who stays on for three years without any truly deep or lasting relationship probably needs a break. I will return, stronger, happier, and in more control of my online and off-line life.

What's in a Profile?

Generally speaking, I don't care nearly as much about what a woman writes as how it is written- not so much the grammar and spelling, but the personality and flair evidenced in the profile. And, of course, if the photos don't make the attraction threshold, I will never get to the text.

The best profiles from either gender's standpoint, I would imagine, combine humor, warmth, and attractive photos.


There are some things that strike me as funny over the past two years- as exemplified by this Letterman type list:

My Top 10 Pet Peeve Women's Profile List:

1) Photoless Winkers- you gotta give me "something" ;

2) Pictures of Pets-cute or otherwise. are you proving to me that you are worthy of animal adulation, at least?

3) Screen Names or self characterizations with "Beautiful", "Sexy" , "Gorgeous" in them- Is there anything less sexy than telling someone how gorgeous and beautiful they are? The harder you sell, the less I believe it.

4) Photos of Sunsets - This is JDate, we want YOU not a submission for Photography School

5) Mother/Daughter shots with undeniably attractive daughters- We all know guys are shallow and overly looks-conscious, so why are we asking for trouble here?

6) Profiles beginning with "this is so uncomfortable".- Don't cvetch about it. (You can talk about just about anything in this section; It does not have to be a perfectly crafted, alluring, and stunningly accurate self-portrait

7) Pet Peeves (Yours) that sound so threatening I get scared!- "the toilet seat, the toothpaste cap, guys who like musicals, guys who hate musicals", "If you wink at me, I will scream, I tell you...don't even think about winking at me ..."

8) Mention of the 'walk on the beach' , "thunder storms" or the "curling up by a fire"- C'mon...even if it's true, we need some originality here.

9) The all too common assertion that there will be "No Game Players for you" -What type of games are we talking about? (absolutely no fun at all, just "This seems like a fit, here's a ring, you and me FOREVER, please pass the salt....");

10) Old Photos, No Photos, or One Photo- Usually people just complain about Old Photos for obvious reasons, even as one would wonder how this would turn out well for the poster or the viewer. So you meet and look 15 years older than your photo and it's going to be "ok"....I don't get it. One is better than none, but my gut reaction is that the poster wants to make the best of one shot that came out better than thousands of others. Four or five good shots become almost indisputable evidence that you look the way you photograph.

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