For years, Cheryl Strayed wrote an advice column for TheRumpus.net called "Dear Sugar." Strayed wrote anonymously—to her readers she was only "Sugar"—and she answered likewise anonymous letters about love and romance, grief and loss, money and family troubles. To call these "columns" seems to sell them short: these are beautiful, heartfelt, brutally honest essays that go in directions you don't expect. Strayed is compassionate with her letter writers, giving them gentle advice while not pulling any punches, but says her real mission isn't to tell them what they "should" do. Instead, she tries to reveal a third way by either presenting a perspective that those who write can't see on their own, or to complexly hash out what's really going on in their life and situation. My favorite essays, hands-down, are The Ghost Ship That Didn't Carry Us and The Obliterated Place. Proceed with caution: this has a hefty f-bomb count and triggers galore, but it's too good to leave out.
