Reading list, question for hardcore readers

Inspired by CaraMama and KZ, I'm going to try to fit in some reading. I've started several books, one of which I can't seem to find in my house anymore and I'm wondering if I left it somewhere. But I'd really like to start speaking like an educated adult again and I'm thinking by increasing my reading, it's gotta happen, right? I mean, er, it must happen, correct? ;)

Here's the short list:

Sippy cups are not for chardonnay (started, not finished)
Reading Lolita in Tehran (started ages ago, still haven't finished, may never since I never remember where I left off, which brings up a good point)

These two could be categorized as reference books but I still want to read them:

Raising a Son (started, LOST)
Toddler

I regularly watch the Colbert Report and he has recently interviewed the writers of some books I think I may be interested in as well. Here's what I plan to add to the list eventually (maybe in between the others -- if that is possible).

The Purpose Driven Life
Red Letter Christians
You're Wearing That?: Understanding Mothers and Daughters in Conversation (CaraMama introduced me to this author ages ago and I've been meaning to read this one but was reminded of it by Colbert)

AND POSSIBLY,
The Cult of the Amateur: How today's Internet is killing our culture

But that might be asking too much for this year. Am I pathetic or what?

Question to the hardcore readers

What if the book just doesn't grab you? For instance, I've started Reading Lolita in Tehran several times and I just can't seem to finish it. It's interesting to find out pre-revolutionary and post-revolutionary Iran but it's really hard to follow -- or maybe that's just me. So when do you give up and why? I feel as though I should finish this book because of it's significance to what our country is dealing with now in regard to Iran. However, for whatever reason, it just doesn't grip me like other books have in the past.