The protagonist of Adelle Waldman's new novel, The Love Affairs of Nathaniel P., is Nathaniel Piven, "a product of a postfeminist, 1980s childhood." We asked Waldman to pick some of her favorite books by authors with different genders than their respective protagonists.

The first question I’m usually asked about my novel, “The Love Affairs of Nathaniel P.,” is whether it was difficult for me, as a woman, to write from the male point of view. The answer is that it was both harder and easier than writing from a woman’s perspective. Harder because I had to re-imagine the world from my character’s POV—he thinks very differently than I do—but also easier because my protagonist, a thirtysomething male writer with a string of ex-girlfriends, was in no sense a stand-in for myself. I could see him more objectively as a result. His “not me”-ness also meant I was less liable to use the novel for my own ends, as a way of presenting a favorable version of myself to the reader.

I think one of the reasons people are surprised that I wrote from a guy’s point of view is that the novel is centered on Nate’s love life and his relationships. (It also has a couple of pretty unsparing—and not at all titillating—sex scenes.) In fact, authors frequently cross the gender divide. We are just more aware of it when the subject is love and sex.
Here are some of my favorite books in which one or more of the author’s best characters were of the opposite sex.

1. Madame Bovary by Gustave Flaubert - It’s hard to imagine starting this list with anyone but Flaubert’s most infamous anti-heroine. Emma Bovary’s idea of love is derived from a clichéd and pretty vulgar version of romance, more dependent on flash and fashion than tenderness. Even so, she is not presented to the reader as an object of scorn; under Bovary’s layers of affectation are real and occasionally touching wells of feeling. Flaubert lays bare Bovary’s failings—he’s merciless—but he doesn’t resort to satire or caricature, and as a result his portrait feels chillingly and unsettlingly plausible.

2. Anna Karenina by Leo Tolstoy - Another author, another adulteress. Tolstoy is, of course, one of the most stunning psychological realists of all time, moving seamlessly into and out of the minds of his many characters. An aspect of his portrait of Anna Karenina that really strikes me is the intricate spiral of despair Anna suffers when she begins to sense that Vronsky’s love is waning. In response, she begins to perform—to fill their household with guests among whom she can be the bubbly and bright head-turning woman she once was. She is trying desperately to conceal the bitterness and fear that she knows will only further alienate Vronsky. It’s a sad, moving and utterly believable detail in a large and wide-ranging novel, but it’s those sorts of emotional details, one after another, that make Tolstoy so remarkable.

3. The Professor by Charlotte Brontë - Moving backward in time to the 1850s, we have Charlotte Brontë’s first novel, for which she was unable to find a publisher until after her second novel, Jane Eyre, became a huge hit. The Professor tells of a young Englishman in Belgium who falls in love with his student, a story that is reprised in a slightly different guise in the romance between Lucy Snowe and Paul Emanuel in Brontë’s Villette. According to Brontë’s biographers, the storyline is derived at least in part from doomed feelings Brontë herself developed for a married professor who taught her when she studied in Belgium, making this an instance where a personal disappointment spurred a work of art—actually two—that would prove to be far more enduring.

4. Middlemarch by George Eliot - Perhaps it seems surprising not to invoke Daniel Deronda, Adam Bede or even Felix Holt: The Radical, books that are, after all, named after their male heroes. The truth is I find Eliot’s perfectly virtuous male protagonists less compelling than the flawed men that show up in some of her other novels. I’m a sucker for a complicated mixed portrait like that of the unfaithful husband Tito Melema in Romola or Middlemarch’s Tertius Lydgate. For my money, Lydgate is one of the best-drawn characters in all of English literature, and his unfortunate courtship of and marriage to Rosamond Vincy is one of the most chillingly perceptive accounts of a certain type of unhappy relationship.

5. Mating by Norman Rush - One of the most famous gender-crossing books of recent vintage, Mating, which won the National Book Award in 1991, is a sharp, elegant and extremely intelligent first-person account of a young female academic’s romantic pursuit of a well-known and charismatic older male social scientist in Botswana. The book feels so intimate that I think many readers found themselves flipping to the book jacket to double-check that it was in fact written by a man.

6. The Emperor’s Children by Claire Messud - Messud’s depiction of New York-based public intellectual Murray Thwaite feels so real that as I typed the name I had to check that I didn’t mix up the fictional character with a real public intellectual. That Thwaite remains as lovable—or at least as human—as he does while balancing wife and mistress (especially given just whom he seeks out for a mistress) is a testament to Messud’s ability to telegraph on the page the intelligence and charisma of this imperfect husband.

7. Freedom by Jonathan Franzen - Franzen’s depiction of Patty Berglund’s fascination with charismatic Richard Katz, which began when she was a college student and reasserts itself when she is a long-married mom, is as complicated and layered—and convincing—an account of a woman’s private romantic torments as any I’ve read. This isn’t a surprise, from Franzen. He previously gave us a stunningly well-drawn woman in love in Strong Motion’s Renée Seitchek. That book is about many things, earthquakes among them, but I’m not sure the romantic insecurities of a passionate, intelligent and self-critical woman have ever been laid out so succinctly—nor with as much genuine affection for the character.

8. Seating Arrangements by Maggie Shipstead - I was blown away when I found out that this brilliant and funny first novel, about the long-married patriarch of a WASP-y family, was written by a woman in her twenties. Shipstead nails not only Winn Van Meter’s attraction to a younger woman and his tenderness for his loyal wife but also various more picayune and comic aspects of his maleness—such as the sense of emasculation that comes from his being a lone man in a household of women.