Do you often feel this way when looking at "old friends

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Yes, it's actually embarassing as some of these people are facebook friends (though we never talk). I am single, make $11/hr, live at home, usually people don't even like my statuses. I would be so ashamed to admit if anything, I seem worse off than I used to. Facebook is just a place to remind me of how much of a loser I am.

You and I must have been separated at birth, considering what you painted here is the story of my life. No friends? Check. No partner? Check. Spotty work history consisting of menial jobs? Check. And guess what? I was always the star student of any class I was in: that's not conceit, that's a fact.

But here's the thing: those 10 classmates you googled don't represent a comprehensive image of the success of your entire peer group. Let's start at the roots here, first there's the dichotomy between successful careers on one hand and happy family life on the other (of course, not mutually exclusive), for you've said: either lucrative careers or a seemingly successful marriage and social life, as I said (and neither you nor anyone is claiming that) the two are not mutually exclusive, and one is not a guarantee for the other. Of the attorney, the entrepeneur, the doctor, do you know whether or not they're having a happy private life? Maybe the doctor is having an affair. Maybe the bank's vice-president downs a glass of whisky every Saturday night before going to sleep. Maybe the entrepreneur had to bury a child. You don't know!
On the flipside, maybe the ones who are doing okay in the social department and have a great group of friends, feel that they are failing in terms of advancing in their careers, picked a course of education that was really fulfilling for them personally, but struggle to find a job in their field of interest; and now they're considering how to go about re-schooling theirselves to procure that financial security.

And that brings me to my next point: it's harder to google the 'bad'.
And when I say 'bad', I'm not talking about embarrassing old videos and photos of being drunk at parties or crashing your car into a store window at age 22.
The attorney is googlable as an attorney, so is the success of the doctor, the VP et cetera. That's what people put on the internet: look everyone, I'm a great attorney! Please use my services!
You're not going to put on Facebook: "Well, I originally wanted to study paleontology, but I was emotionally struggling while living with my alcoholic father in my late teens, so university kind of went on the backburner for a couple of years, and I scrubbed toilets instead trying to make a buck and when time came around for my enrollment exams, I got this huge fright and I called the whole thing off halfway through." You're not going to see those things online. People present the good stuff online, and if they don't have so many great things to report, they'll just keep quiet about it.

Those 10 classmates you found may have been successful from a certain point-of-view, each in their own respective ways. But they do not provide the whole story; they're keeping the not-so-nice bits for themselves. And among all the other classmates you didn't find online, there may be a lot who are feeling the same as you and me, thinking "Wow, this is not what I had imagined for myself when I was 15".

I googled my friends. I used it to reconnect with them on Facebook (which, though initially met with enthusiasm, did sadly not result in a reunion). I also googled myself. It doesn't yield much, except for my comic book forum profile, and my activities on an Indonesia-related blog. But in terms of how I fare in society, there is nothing. I have no LinkedIn profile. My personal life is ungoogleable. Ergo, as of now, no classmate would be able to find out whether or not I ever got that biology doctorate I was so bent on getting, at least not by consulting a search engine.

So in conclusion, googling your old classmates provides a cock-eyed view of the current state of things, and you must remember that appearances can be deceiving- and the grass is always greener on the other side.

You know when you go on facebook or look up old people you knew from elementary school that you may have been kind of friends with and actually felt comfortable with? When you look at these peoples pictures ect today, do you often feel like their social skills, job status, and other abilities are so superior to the areas you struggle with, that they almost look intimidating to you know. In other words, if you were to meet these people today, would you actually feel uncomfortable or intimidated if you were forced to hang out with them today? It's kind of a strange and somewhat unpleasant feeling but when I look at a lot of these people, I definitely feel that way.

they are on their life track, and I am on mine, and never the twain shall meet.

I wanted to cross the street to avoid them even back then.

Oh, yes, I understand. Back than I had my own side paths and never went direct ways they used.
But now 20 years later reasons to avoid them are different.
It is not a fear now, but... maybe slight disgust. Not sure but it feels close.

I was just never compatible with anybody else.

I am done comparing myself. I look at me and only me, and see what progress that I am making. That's enough. The rest is BS and it gets in my way.

Never at all?

This is exactly why I don't use a lot of social media, because even when I try to rationalize that people there are not necessarily showing what their real lives are like on there, it skews my perception of them heavily and makes me feel extremely inadequate and depressed because I don't have some of the things they have.

Social media is not a reflection of real life though, and that is why I don't use it or trust it. Work related social media is useful, but personal mediums, in my opinion, can be extremely damaging to one's sense of self-worth, in that if you are different or even feel different, it makes you feel secretly ashamed of these tendencies. It does a thorough job of hiding what people are actually like in real life, and I believe that it distances people who think differently by reminding them of how much they are not like others, even when you have tons in common with people who gloss things over. It is a living example of pluralistic ignorance.

I highly prefer cultivating individual relationships with people rather than passively viewing the glossed over versions of their lives. I want to know about the troubles they are having with their friends and significant others, the disappointments in their lives, and their shortcomings and inadequacies. I want others to remind me through their interactions with me that it's okay to be human and imperfect, and that it's totally okay to have flaws. I want to be reminded that many of these people, even those who strictly abide by impression management can think for themselves and are human, because they are.