Roiphe's second book was 1997's ''Last Night in Paradise: Sex and Morals at the Century's End
. She also began to contribute reviews and essays to Vogue, Harper's, Slate, The Washington Post, and The New York Times. In 2008, she published an essay featured in the anthology Thirty Ways of Looking at Hillary: Reflections by Women Writers.'' In her essay, entitled "Elect Sister Frigidaire", Roiphe writes that Hillary Clinton is "in many ways the feminist dream incarnate, the opportunity made flesh, the words we whisper to little girls: 'You can be president. You can do anything you want.'" Reviewing the book for
The New York Times,
Michiko Kakutani noted that some of Roiphe's observations were in "stark contrast" to what Kakutani considered some of the "antifeminist" pieces in the collection. She has also written a novel based on the life of Lewis Carroll and his relationship with the real Alice, called
Still She Haunts Me, which was published in 2001. In 2007, Roiphe published
Uncommon Arrangements: Seven Portraits of Married Life in London Literary Circles 1910-1939. Donna Seaman, in the trade publication
Booklist, gave the book a starred review, writing, "Roiphe, inspired aesthetically and philosophically by the writings and lives of these social and artistic pioneers, offers sophisticated psychological, sexual, and social analysis, fashioning uncommonly affecting portraits of uncommon men and women." In
The New York Times, the editor and critic
Tina Brown called it "the perfect bedside book for an age like our own, when everything is known and nothing is understood." In
The New York Observer, Alexandra Jacobs conceded "Katie haters will be sorry to hear that it’s very absorbing. The author has done something constructive, for a change, with her contempt for the contemporary age’s lily-livered female psyche..." Roiphe responded to some of her critics in an essay in
Slate including
Gawker. In 2012, Roiphe published the essay collection
In Praise of Messy Lives. In
The New York Times, critic
Dwight Garner praised the book, writing, "I’ve begun recommending it to people, particularly to would-be writers, explaining that Ms. Roiphe’s are how you want your essays to sound: lean and literate, not unlike Orwell’s, with a frightening ratio of velocity to torque.... Among Ms. Roiphe’s gifts is one for brevity. She lingers long enough to make her points, and no longer. If I could condense my opinion of her new book onto a T-shirt, that Beefy-T would read: 'Team Roiphe.'" ==Controversy==