Tiny Beautiful Things, by Cheryl Strayed: Writing as "Sugar" in the "Dear Sugar" advice column for The Rumpus, Strayed's collection of advice is less about the advice and more about finding a friend on the pages. She offers up a near-perfect balance of kick in the pants, shoulder to cry on, and downright hilarity for advice ranging from "My son is gay, now what?" to "I hate my parents, and they hate me," to "I've never been in love." Her stories are peppered with her own experiences, which only makes them all the more colorful and endearing. Buy here ($14.95).
Bonus: Wrap Tiny Beautiful Things together with Strayed's memoir, Wild, about her solo hiking trip on the Pacific Crest Trail. Buy here ($14.95).
Traveling with Pomegranates, by Sue Monk Kidd and Ann Kidd Taylor: Kidd is perhaps best known for her wildly successful novel, The Secret Life of Bees, or maybe The Mermaid Chair. But before novels, she wrote non-fiction about religion and spirituality. In Traveling with Pomegranates, she returns to her non-fiction start, this time with the help of her daughter, as they recall the shift in their relationship as Ann grew into an adult herself. It's a touching, moving story about mothers and daughters, finding faith in the least likely of places, and the power of travel to shift out perspectives. Buy here ($15.00).
Bonus: Wrap Traveling with Pomegranates with The Secret Life of Bees (buy here, $16.00), or give a gift card to your local indie so the receiver can be first in line to purchase Kidd's newest novel, The Invention of Wings, when it hits shelves in January (pre-order, $27.95).
Bonus: I'm not sure it's possible to be a teenager and not fall for one (or all) of John Green's books.
Bonus: Throw in a copy of Chuck Wendig's Blackbirds, and you'll give your reader not one but three books to love, as it has a sequel already and a third book coming out this December (though Wendig himself assured me that each book can also stand on its own). (Buy here, $7.99).
Bonus: These two volumes are part of Alain de Botton's School of Life series. Add How to Stay Sane, and, if appropriate for the receiver, How to Think More About Sex, and you'll have your self-help junkie hooked on this little series as new volumes are released. Buy here ($16.00) and here ($16.00). Or branch out of this series with the hilarious but also informative How Not to Be a Dick: An Everyday Etiquette Guide. Gift carefully, though, lest someone take offense. Buy here ($16.99).