Lets say due to some weird dynamics of time and space your past self can see you as you are on December 17th 2010.
Which past self would be most shocked at meeting your present self.
My own example, my 14-16 year old self would be absolutely mortified at my 26 year old self. He is a Lawyer, he loves to wear suits (past self hated them the idiot) and he is much much more conservative in outlook and politically.
Your answers!
My old drinking-and-drugging self (ages 17 to 30) would be pretty surprised at my current self…I don’t do anything beyond 2-3 beers anymore, and don’t even have the desire or stomach for more than that.
My 15 year old self would never go bald, get fat, wear a tie, and work in an office. He’s still looking forward to becoming a rock star.
My 16-year-old self would gawk at the fact that I can go for spans of months without listening to Nirvana, that I’m doing well in college, that I love football, and that I can talk to women without being enveloped in nervousness and anxiety.
I’m sure my teenage self would be astounded that I’m not an engineer, I wear glasses, my hair pretty much consists of “scalp” and I don’t play RPGs…OTOH I have no problem asking women out, I’m not nervous around small children (g/f has a young son who I think is a great kid) and I can run 50 miles.
Despite the fact I love my wife and find her beautiful, my teenage self would have told me I should have held out for that super model that clearly would have married me had I tried harder.
My 20-something self who worked in pharmaceuticals and made next to nothing as a lab researcher, but who was saving the world, would be absolutely mortified at my 40-something self today who makes a great salary, wears a suit instead of a lab coat, and works in the defense industry. He would tell current me what a piece of shit sell out I am… He’d also tell me I need to lose weight (well, he’s right about that), because 20-something me used to have the time and inclination to work out 4-5 days a week and was in great shape.
My 21 year old self would wonder how I didn’t manage to stay in great shape, especially considering my current self does not drink nearly as much as my 21 year old self. My 21 year old self would absolutely call me out on this and probably start a fight with me. The real question is: could I kick my 21 year old self’s ass when provoked?
He would also probably be surprised that I didn’t have kids sooner.
Any self prior to about 6-8 years ago. I would never have believed that I’d end up a mechanical engineer aiming to work in aircraft safety with a hockey and football obsession. I surprised myself recently by choosing to go to the Grey Cup parade! Heck even living in Montreal seemed unlikely back then. Past-selves would have expected me to still be stuck working in pharmaceutical labs and probably having a kid or two by now, rather than finishing up that mech eng degree (mnemosyne, BSc, BEng) and considering not having kids for several more years.
But those past selves didn’t really know what she wanted out of life, and spent a lot of time trying to be who she thought others wanted her to be. She had never really explored her own interests and was actually a little bit afraid to admit that she liked drinking beer and watching sports, because none of her female friends did. She had never considered engineering, not because she’d been told it was for men, but rather because she’d never been exposed to it as a possible career path and didn’t know any engineers at all.
I’m a lot happier now than I was, because I’ve started to allow myself to be who I really am.
(ETA: and my husband thinks he lucked out - beer, sports, airplanes…what more could a man want? hehe)
In the middle of grad school - so, age ~26 - I had been through a few failed relationships with women, and I was in grad school primarily to avoid growing up, getting a job, and becoming an adult. At an SAE conference in Detroit around that time, I met up with a recent graduate from my department and learned that he was now married and owned a home in a Detroit suburb. He was a nice fellow, but all three of those things - being married, owning a home, and living anywhere near Detroit - were so repellent to me that at the time, I wanted to go hide in a cave just for having talked about it.
And now here I am - 40 years old, married for five years, homeowner for 7 years, and an Ann Arbor resident ever since I finished grad school about 12 years ago. upon meeting the current version of me, the 26YO grad school version of me would have seriously contemplated suicide. Not that life now is bad - it’s pretty good - but the 26YO grad student had a somewhat warped outlook.
My pre-teenage-years self would be mortified by all the bad words! that I use. My early teenage self would be shocked that I was wearing colors other than black, and that by now my hair wasn’t dyed about fifty different neon hues.
My 10 year old self would be appalled to see me with long hair. I was stuffily conservative back then and very disapproving. I would not have approved of the me that I became.
The 18 year old valedictorian me would be appalled that I never graduated college and would slap me silly for not keeping up with my saxophone.
Conversely, I wish I could advise my 18 year old self that choosing a major just because it pays better, and not because I like the material, does not lend itself well to degree-completion.
My 16 year old fundamentalist self would fear I was going to hell for 1) not believing there’s a hell, 2) being pro-choice and 3) a liberal in general.
I guess I’m the weird one. My 20 year old self would look around at my life and say “That’s about what I expected. Well done”. My 32 year old self (I am 34) would be shocked: two years ago, I was morbidly obese, had more debt than I was comfortable with, and was reconciled to the idea that my life was set: tomorrow would be much like today for the foreseeable future. And I was really ok with that. I really had a pretty good life. I was doing good in the world and perfectly content.
Then we decided to have a child–something I’d put aside because I wanted my husband more than a child, and I didn’t want to twist his arm. But he changed his mind, and it was like a switch flipped in my head. Eighteen months later, I’ve lost 45% of my body weight, our finances are in terrific shape, and I have such a different view of what the rest of my life (may) be like. This me is much more what I hoped to be at 20, so I’m pretty happy–but I really wasn’t unhappy before.
Even the 20 or 21 year old version of etv78 would be grossly disappointed at where my life went (or didn’t). He expected to be a lawyer, or maybe a teacher (that came slightly later), and eventually a politician. He’d be despondent that of all the people he knew around that time, and slightly before, I have the LEAST to show for my life!
My fifteen year old self would no doubt be shrieking “We have a KID?!?!??!” Also, “What with the cats?” And she’d no doubt be both disappointed and disturbed that I didn’t find a way to parlay my fabulosity into millions, in an age of reality television no less (my fifteen year old self was seriously poor, eminently pragmatic, and more focused on money than dignity, like a fifteen year old will be, what can I say?).
On the other hand, she’d be pleased I never married, proud of my career and my financial independence as a single mom, impressed by my (modest) art collection, thrilled to see a room dedicated to books, and grateful I didn’t become my mother.
I don’t think any version of a younger me would be shocked at the facts of the older me, apart from my weight.
Maybe a relatively recent younger me from say… 6 or 8 or 10 years ago would be shocked (and bummed) to see that I’m alone, since that me had not planned that. (Although again…shocked? Not really. Sad. Not shocked. There was a huge age difference - 15 years - that I was always afraid would prevent us from staying together forever.)
Most of my previous selves, from the 12-year-old that was first interested in girls, to the 17-year-old about to graduate from high school, to the 22-year-old just graduated from electronics school, would be dismayed, but not completely surprised, by my present self.
No girlfriend or wife? That’s not a surprise at all. He would be surprised at the depth of struggle required to learn to be sociable, and I suspect a few things would knock him back, like learning about prosopagnosia and its effects on social development. He’d be relieved that I at least had some chance for intimacy, even if it was not to last more than a few months.
He’d like my Mac, though. 
The angst-ridden 20-year old septimus would be surprised and delighted to see me pleasantly retired with a wonderful wife and two happy kids. The renowned 30-year old technogeek might be disappointed, though probably not surprised, to learn that septimus achieved little fame nor fortune. The 40-year old playboy would be relieved(!) to see septimus settled down with one true love.
Apart from a mild disappointment from my teenage self that I gave up on my dream of becoming an actress, I think every version of my past self would be pleased and proud with what we’ve achieved. We have a happy marriage, a succesful career, a nice home, fantastic friends and a very fulfilling social life. Plus we still look good. That’s pretty much (bar the famous actress thing) all we ever wanted.