Is your teen a boy or a girl? And what age? Both those could have an affect on the answers to your questions.
First, let me suggest that you open a series of threads on the appropriate forums here. That way we can attack the problem piece by piece, and with specifics, instead of keeping it too general over here. For instance, you say "main dishes and sides." But we can help better if you say "pork chops" and "root vegetables." Or even open a thread on menu planning that asks, what's a good way of cooking a whole chicken, and what to serve with it?
Next, see if you can find a copy of "The Joy Of Cooking." Older copies actually are better, if you can find one. But even the latest edition is a good, basic introduction to the how and whys, as well as the whats of cooking.
He/she will still find terms and techniques that need explanation. But that's when you turn to the forums. And keep in mind that google can be your best friend.
On bread making, hands-down the best book on the subject is Peter Reinhart's "The Bread Baker's Apprentice." Peter really explains the science behind bread, and you come away with an understanding of the process---which, with bread making, is a lot more than blindly following a recipe. Of which, btw, he has some great ones.
So, maybe one or both these books should find its way under the Christmas tree this year?
I don't do sweets myself, so can't recommend any basic books on baking cookies, cakes, and pies.
Menu planning is, itself, an art form because it's based not only on making the individual dishes, but understanding how their flavors work with each other. Many printed recipes include suggestions along those lines, i.e., "serve with X and Y." But really understanding these relationships comes mostly from time in grade. The more one cooks, the more one has a feel for what works and what doesn't.
Make sure you child understands one thing: Short of actually burning it, there is no way to destroy a dish. It may not turn out quite the way the recipe writer had in mind, but so what? And if it turns out to not be to everyone's taste, well then, next time you either don't make that one, or figure out how to improve it. In short, our mistakes are our best classroom.
One help is to read the upscale cooking magazines, such as Gourmet, Bon Appetitie, Saveur, and Food & Wine. To be sure, they are a little high-class and gourmetish for a beginner. But they are a great classroom for both regular dishes and menus.
I would choose just one of them, at first, and get a subscription. Bon Appetite probably makes the most sense, because of the sorts of things they cook and they way they present it.
I AM SIMPLY THANKFUL NOW FOR THE MEMORIES AND THE EXPERIENCE OF CANNING. I WAS READING YESTERDAY THE THREADS ON TOMATOES AND THERE WERE POSTS IN THERE ON CANNED TOMATOES AND I JUST NEVER WILL FORGET THOSE YEARS OF EATING MY OWN HOME CANNED PRODUCTS, SIMPLY NOTHING TOUCHES IT! I HOPE THAT THERE WILL BE A NEW GENERATION OF COOKS THAT WILL CARRY ON THE TRADITION OF CANNING!