Sorry about the delay in reply here. Bear with me. Quite a volley of stuff was thrown out there and I've had to topically parse things a bit here. I really appreciate what you have to say here, Kamikaze. You more-or-less covered what I would have said, and seem to get where I'm coming from a good bit.
Sincere apologies if some of my retort sounds a bit pedantic. I'm really just trying to be clear about my experience and perspective here:
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I am surprised you referring to pof or OK Cupid or tinder as sites for educated people. These are hook up sites primarily or for people who can't afford memberships on paid sites or are too cheao. Sure some people met others on those but those aren't plenty.
I have not heard of any intelligent employed professional who is looking for serious relationship on there. Creative? Progressive? On free hook up sites? You kidding? women of class aren't there. Trust me. And women don't like men who use unpaid sites.
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Divine, in my experience, OKC has been one of the best sites for matches and availability. Definitely better than Match, POF, eHarmony, etc. Having to pay for a subscription does not guarantee that a site is decent, sadly. Oh, and I'm educated and have encountered other educated people on OKC. There really are all sorts of people on there. (Personally, I would never just hook up with someone, and I don't care if someone pays for a subscription or not. I only care about the quality of the person.)
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I think it's a tough scene out there, especially as we get older. Not to mention if you're off the beaten track/not as mainstream, that makes it tricky, too. I think different groups tend to focus on different sites, perhaps? For instance, I think OKC may appeal more to people who don't fit so neatly into the traditional categories. I've seen way more transgendered people on there than on any of the other sites, for instance.
I am actually close to Burnt's age, and of course I have a career as well. Yet I prefer the variety and quirkiness of the people on OKC because I am a quirky sort. I also like being able to message and see their information for free. I actually have a paid account, but I like that they don't force it on you. Few sites allow people that freedom anymore.
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While personal experiences and regional demographics may absolutely vary, I think you'd be hard pressed find too many people who didn't agree that Ok Cupid leans a good bit to the left, tends to skew on the college educated & secular side of things, tends to draw more on the pre-first marriage end of the continuum, and is preferred by the proverbial "freaks & geeks" types.
In fact, the gist of their demographics is published in Christian Rudder's book
'Dataclysm (Who We Are When We Think No One's Looking)' which is about big data. The guys who started Ok Cupid are MIT grads who are math/data geeks. It's been as much of an exercise in trends in big data as has been about being on online dating site. Rudder laments this point in particular in the chapter about race, knowing their user base was inherently more progressive than the norm. It's a phenomenal (and somewhat depressing) book by the way.
Plenty of Fish, Match, eHarmony, etc. all have been much more conservative, traditionalist, religious (eHarmony in particular), and less educated (PoF in particular), in my experience.
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I don't know why you are referring to yourself as millennial. You are almost 40.
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Millennials could certainly be in his dating range as the transition point between the two is supposedly early 80s.
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There's no hard agreed upon date on when the Millennials start. Some say as early as '77 (my birth year) or as late as '83. Some say there's a "lost" generation in-between Gen X'ers and the Millennials. I personally don't put myself under either moniker. At best I'll timeline myself a late-bloomer from the end of Gen X, but in general I personally identify more with the Millennials: My tastes, my experiences, and my worldview tend to line up better with people in that bracket. I got through college on schedule, but my career (like many ID career paths) was a bit more of a waiting game. And then like many Millennials, I got laid up by the '08 recession right when I started building my career, and pretty much spent the first half of my thirties looking for work. It was absolutely brutal.

I burnt through my entire life savings built up to that point. I finally got a job in 2013 (at age 36). This is part of the reason I'm where I'm at. I feel like I'm playing catch-up. That's not to say I don't have friends and associates my age. I do, as well as friends significantly older, and notably younger than myself. I always have had a diversity in my social circle though. That goes back to high school. It's all about interests and mindset for me.
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No need for pics of family or friends on there. No one wants to see those.
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See, I've been told that pics with friends show that you're not a weirdo that people don't want to be around, and pics with family demonstrate that you care about your family.

I don't have a friends group one on there now and haven't always had the family one. I'll take it off, but I'm pretty sure that's not the proverbial chink in the armor here.
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I am a decent looking woman but when I used dating sites I never thought of putting 6 pics. One can see how I look on two. Why so many?
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I've had as few as three or four. I think there's only five on my Tinder profile now. I was just going for a little variety.
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I am not saying you are too good to be true but you kind of describing yourself as you are. You are saying you have low self esteem but you don't come across that way. Are you humble in your profile?
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I have a... um... "confused" sense of self esteem for lack of a better term.

I work reasonably hard to make myself the best I can be. I'm a designer by trade and by nature I pay attention to the details... so when I get up in the morning, put the energy into getting ready: I look in the mirror and see someone I genuinely think is a pretty good looking and cool guy, but in the back of my brain, the logic department doing the math on all the opportunities that aren't there... weeks, months, years without matches... it says,
"Field reports say you're still a hideous pile of s**t." I've got some pretty thick skin, but Maslow would agree that you can't spend years on end with no positive reinforcement and not start to break down. I get really depressed about it if I really think about it... like bad depressed...
And, yes, as far as I know, I'm humble in my profile. I'm naturally pretty humble as I'm of the opinion that more you know, the more you know you don't know.
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Do you describe yourself as freelance? It often means unemployed or not having steady job. Maybe just say you are designer and then explain what kind when you have a date.
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On dating sites, I've been listed as a 'Sr. Industrial Designer and R&D for Product Development' for the last three years. On here, because
I am wantonly freelancing/contracting at the moment. Thirty seven people were recently laid off from the company that I was working for and I was one of them. I already had some semi-regular side work going with my old bosses new startup (which has over a million in pre-orders already), and I've decided to take the time to evaluate what I want to do next rather than just blasting resumes out at anything and everything. I made rather good money at my last gig, and my freelance rate is $60/hr. So I'm doing okay with just the freelance. I'm one-hundred percent debt free (not even a car payment), several years worth of money in the bank, and I live pretty frugally in most respects, so I'm using the time to re-center my bearings, spend some time on some self-improvement, particularly my health, and move forward in a calculated manner. Just got to thinking tonight that I might go to my dad's summer home in Daytona Beach for a few weeks and work remotely from there for a change of scenery.
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What age women do you want to date? Judging by the kind of sites you use, you might be going for young women . They don't want 40 year old man. Go for women your age or even a bit older. The very fact you refer to them as "girls is kind of strange. What age are you considering?
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Also, I often say "boys/girls" myself. It's just a preference/quirk of word choice. Nothing more than that.
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Yeah, I think for me it's a New Yorker (where I grew up) thing. I call groups of people "you guys" even if it's a group of ladies or mixed gender.
As for my considerations, I'm keeping a range open because you never know... you know?

What's more important to me is that our respective places in life line up more than anything. I tend to focus a few years younger than myself, then work my way outwards in either direction. My experience has been contrary to what you say above, though. Women closer to my own age tend to be less responsive and/or interested than younger ones. The last date I went on (~3 years ago) was 30, and my last girlfriend about a year earlier than that was 24. She contacted me first, BTW. Even then, my search range cut off a good bit over that... but like I said, you never know. Women aren't a hive mind with one universal outlook. I'd
like someone around-ish my age, but it's not a high priority for me. There are much more relevant variables, IMHO.
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I don't know. I know geeky techie guys. Heck my own brother is. They don't grow beards like this. The only guys with these long beards I know are my fiancée's relatives ( also long hair and drinking horns ). They aren't techie. Lol They kind of duck dynasty look alike ( not him, just his family, he is a bit of an outcast).
I am not saying you got to lose your beard though. But you have nice looking face and beard covers much of it. Like you are hiding. Personally I'd like to see the whole face.
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With all do respect, I'm not going to beat the beard thing to death (or my hair... or my fashion sense), so if that's all that this is going be about, I'm afraid I'm done here. Fact is, I have only had a beard for about a year now, before that I was clean shaven. I was online dating for almost five years without one and getting a similarly hollow result. Heck, one of my pics on my profile (the one of me playing guitar live) is partially on there to show that I'm not hiding anything under my beard. I've joked about it in the caption.

Also, I've
never had a Duck Dynasty beard. It's rather short-ish at the moment, a stiletto style, edged nicely and faded to a clean neck-line... but even when it was longer, it was meticulously shaped and cared for (it's a lot of work, FYI). I got regular compliments on how good it looked. Never have I had a scraggly, hillbilly beard. You can toss out the pejoratives "hipster" (though I'm more metalhead than indie rocker) or "lumbersexual" (though I don't own a stitch of flannel), but racist mountain hick doesn't come close to applying here. Finally: I'm not shaving it. I probably eventually
will shave it (I like to change up my style fairly regularly), but the fact is I see guys all over the place with beards with perfectly lovely girlfriends. They're usually a bit on the alternative side themselves, but that's kinda the point. Again, it may be a regional thing with Divine's locale, but most major cities I've been in, the beard thing is kinda a thing... particularly in alt/creative/muso circles. Same goes for undercut hairstyles. Women even put this stuff on their profiles, "I like beards", or message me if "you have a beard". What those guys are doing right, I dunno.