First thing. Go rent Who's Afraid of Virginia Woolf. Or read the play by Edward Albee. Then read The Gum Thief by Douglas Coupland.
(I can already tell one of the disadvantages of this blog is when I start to write about books I've read and liked, it makes me want to sit down and read them again.)
Two lonely lost souls, Roger and Bethany, meet while working at Staples. Roger is middle-aged, divorced, depressed, and writing a novel called Glove Pond that's a lot like Who's Afraid of Virginia Woolf. Bethany is 24, lives with her mother, wears a lot of black, and is as depressed as Roger. When Bethany finds out that Roger is keeping a journal at work, she reads it. And then adds comments of her own. Roger and Bethany don't speak out loud to each other at Staples, but continue to exchange journal entries and share information about their unhappy lives.
Sounds grim. But it's not. If you've ever read Coupland before (Generation X, Microserfs) you'll know how funny he is. The details of working at Staples - hilarious. Sections of Glove Pond appear in the The Gum Thief and you'll laugh out loud at the awfulness of Roger's writing - but it's also surprisingly moving in the way Roger incorporates his life, and eventually Bethany's in his book.
The heart of The Gum Thief is watching two people who have given up on life, find friendship and where they fit in the world.
(And yes, after writing this, I am reading The Gum Thief. Again.)