My teenage self would be absolutely freaked out at how his life turned out. I would not have expected anything that’s happened to me to have occurred. I moved to Florida, married a wonderful woman, got a job in radio, a house in the suburbs, some great new friends, all the toys I used to wish I could afford… all that would have been unthinkable thirty years ago!
I love this question. I think about this a lot.
My teenage self would be horrified that I’m fat. Well, it would seem fat to her.
My teen self would probably go on a days-long crying jag if she found out that in my forties I was divorced and childless.
Nothing could induce my teenaged self to believe that I had joined the army and liked it.
Once she got over the crying jag and had accepted what she saw as my unhappy fate, she’d probably think my job was really cool and my house really nice.
Then she’d wonder how I could possibly ever have gotten so confident, assertive, and competent.
He’d be aghast and dismayed at my hair or, rather, the lack of it. Man, I had some great hair back then.
He’s also be shocked at how much I exercise now (1:50 1/2 mary - whoo hoo!). It doesn’t quite fit with the cigarette-smokin’, McDonald grubbin’, bong hittin’, Cheeto munchin’, swill slammin’ lump I used to be.
When I was a teen, the idea of living in California was completely foreign.
Work-wise, what I fully expected I was going to be doing is a dead art today, and what I am doing did not even exist then. Back then, computers were these mythical things that sent you a punch card to mail back with your check to the phone company when you paid the bill. I was going to be a TV repairman, but now, TVs are disposable and the fix-it shops are gone. Instead, I’m a computer security specialist.
That I’m an accountant with a mortgage and living in Iowa instead of a poor marine biologist living in Southern California.
That I did not off myself at 40 in despair at having become my mother.
That I am married, and am happy about it.
That I actually quite like myself these days.
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Still being alive at 32.
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Being married
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Eating and actually liking: sushi, broccoli, wine, hummus
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Not having a college degree
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Living in suburbia
He would be shocked at the hair loss,and the beard, I had pretty long hair in high school, but couldn’t grow facial hair to save myself. Also that I am very successful in my field and make pretty decent money, something that in high school I never would have thought would have happened. I think my old self would be shocked at who I am married to now and how happy she makes me 
It would blow my teenage mind to know that, yeah, I did turn into an adult with a good job, cute fiancee, nice car, etc.; as I expected…
…Only now I drink alcohol, never went to college, rarely go to church, and have been known to smoke a doobie every once in a while.
I was a bit of a square when I was a teen.
18 year-old self would be shocked at my annual salary (along with my wife’s salary) and wonder why we aren’t living in a McMansion driving expensive cars.
The big one is that I want to have kids–up until…oh, age 28, I swore I would never have them.
I think I’d be pretty shocked that I’m a lawyer. Hell, I still want to give Mr. Snapp the finger and tell him I didn’t need algebra to be successful. In a way, I often feel like the same goofy kid I was–it’s weird to think that I help other goofy kids for a living!
My teenage self?! Heck, my self from two years ago would wig out if I told him what would happen to him. He’d never believe me.
I voluntarily wear my hair at or above shoulder length. (the hair thing seems to be a common theme here)
Honestly everything else I probably would/could have predicted. It sort of creeps me out sometimes.
I expected to go to law school, and then have one career for the rest of my life. I thought I would like it that way. I thought I would place financial security over other considerations, like job satisfaction. I did graduate from law school, but quickly left the law to find a more satisfying career, despite the financial risk involved.
Being happily married, having an education, planning to go into a career where I will become “The Man”.
After due reflection, I’d have to say…nothing. Not only was he a fairly unflappable brat, I haven’t changed all that much in the intervening years. I’m not in the exact line of work I was thinking about back then, but I’m still a techie, and I do real engineering on the side.
He’d probably be jealous of my gaming gear and my internet access, though. He had to make do with 8 bits or less and a 300-baud link to a BBS.
It would have been unfathomable that I let myself get so fat. I distinctly remember once looking at women about my size walk down the street and thinking, “That is so GROSS! If I ever got like that, I’d just stop eating entirely, that’s all!” Well, yeah. Not so much.
That I live in an apartment, and furthermore that I don’t WANT a house. When I was growing up I thought apartments were trashy and low-class. I couldn’t figure out why anyone would throw away that kind of money and not own anything as a result. Yet I’ve been happily living in apartments for 10 years now, and every time the boiler blows or the sink backs up or my kid locks herself in the bathroom, I breathe a sigh of relief that it’s not my problem, pick up the phone and call the landlord.
That I’m going back to school at age 33 to become a nurse. My mom did one of those unintentional sabotage things we do to our kids: when I was young, she told me how lucky I was that post-feminism I could be anything I wanted in life. When she was a kid, she said, women could only be teachers or nurses (and teacher was preferred, since they didn’t have to look at naked men’s bodies.) She meant, of course, that I could do anything I put my mind to. I heard that being a nurse was only for stupid backward women who submit to patriarchy. So even though I thought medical stuff was cool, and I went to a community college with a great nursing program, I just took gen ed liberal arts stuff in the hopes that I’d someday figure out what I wanted to be when I grow up. Turns out it’s a nurse. Whodathunkit?
I think my teenage self would be scandalized that I ended up as an AP exam reader, since I was convinced for most of my teenage years that ETS was Evil Incarnate. (Actually, I still feel like I’ve Sold Out To The Man every summer.)
My teenage self would probably also be saddened, though perhaps not completely surprised, by my lack of a husband and children. Then again, my adult-self is also saddened but not really surprised by this.
Other than that, I think I ended up with more or less the life I wanted – a low-paying but enjoyable and useful job as a college professor, lots of travel, a novel in (slow) progress, a low-environmental-impact and low-consumer-goods lifestyle. Teenage-self would be particularly pleased by the fact that I don’t have a TV, though I don’t know what she would make of my Internet addiction.
I didn’t marry my boyfriend from then. I also didn’t marry a tall, thin, blonde-haired, blue-eyed, pale skinned guy - the only similarity to my then-“ideal” is that he’s tall.
I’m a vegetarian. I really liked meat back then.
I didn’t hook up with some amazing job, but I’m OK with that. It’s pretty cool, just not the world-shaking thing I dreamed of.
I drink alcohol. In fact, I love beer.
Not only do I cook, I adore doing it, and am a pretty decent home cook. My teenage self only helped in the kitchen if cookies were involved.
I don’t go to church and I’m okay with that.
That I’m not a professional archaeologist.
That I didn’t marry my then girlfriend.
My teenage self would be really surprised that I’m alive at all. I can clearly remember being absolutely positive I would not live to 40, and I’m well past that now.
As several others said, she’d be surprised that I’ve gotten fat. I love it when I see 20-year-olds on television talking about how they’ll never, ever be fat! Hah…just you wait.
My teenage self would also not believe I do not live in the city, that I not only do not take drugs but can’t even remember what it was like to do so, and she’d definitely freak if she saw that I no longer smoke cigarettes–and I like not smoking cigarettes!