1) One book to read:
Invisible Cities by Italo Calvino
2) One movie to watch:
I'm going to cheat and name a trilogy: Krzysztof Kieslowski's Three Colors Trilogy, especially the Blue and Red segments. Those three have as much to teach you as anything out there on film.
3) One food to eat:
I can't guarantee you'll like it, but you need to try tapioca pudding, made with real (non-instant) tapioca, whole milk, and a vanilla bean before you can say you hate tapioca. The lactose-intolerant may pass up the tapioca pudding in favor of muhammara, a Middle Eastern dip made of roasted red peppers, walnuts, and pomegranate molasses. Actually, all you tapioca eaters can add muhammara to your lists too. I doubt I could keep you from it once you'd tasted it.
4) One place to go:
Not a place but a process: any trans-continental car or train trip. The cliché of learning about yourself on these trips exists for a reason.
5) One life lesson to leave behind:
Spend some time outside every day, no matter how bad you think the weather is.