Despite its determinedly sprightly tone, the chief impression left by Elizabeth Gilbert’s “The Last American Man,” a book-length profile of one Eustace Conway, is that of a terrible loneliness. At one point Conway compares himself to Ishi, the sole surviving member of a California Indian tribe who was taken in and studied by anthropologists in the early 20th century. “[I'm] the last of my kind,” Conway laments, “stranded. Just trying to communicate. Trying to teach people something. But constantly misunderstood.”

Gilbert thinks Conway is the last of his kind, too, but they seem to have slightly different conceptions of what his kind is. Conway sees himself as a woodsman, in the tradition of such boyhood heroes as Daniel Boone. As a child he embarked on an extremely methodical and focused campaign to teach himself how to live in the wild, and he became very good at it. He’s an expert hunter who knows how to turn his prey into clothing as well as food. For years at a time he lived in the forests of North Carolina in a teepee he made himself. He carved his own bowls from wood and made his own pots from creek clay. He wove baskets and started fires without matches. He hiked all 2,000 miles of the Appalachian Trail, eating only what he could catch or forage along the way. He rode a horse across America.

Gilbert sees Conway as both the consummate woodsman and as the last specimen of something she holds dear, a classic American man. It’s not quite clear if Conway himself finds the question of masculinity very compelling (although at one point Gilbert describes him as regretting the vanishing of coming-of-age rituals for boys), but for Gilbert it’s the crux of the matter. For her, Conway truly is what the rest of American men can only imagine themselves being; “computer programmers, biogenetic researchers, politicians, or media moguls” may call themselves “maverick,” or “pioneer,” but Conway is both things in actuality.

“He makes true a notion of frontier identity that has long since passed most men of his generation, most of whom are left with nothing but the vocabulary,” Gilbert writes. “We’ve based our American masculine identity on that brief age of exploration and romantic independence and westward settlement. We hold on to that identity, long after it has any actual relevance, because we like the idea so much. That’s why, I believe, so many men in this country carry a residual notion of themselves as pioneers.”

All this makes Conway the walking embodiment of archetypal American manhood: resourceful, competent, intrepid, independent. A heavy symbolic load to carry, but Conway does seem up for the job; “I’ve never found anything to be particularly difficult,” he tells Gilbert (though we later learn that’s not entirely true). Most importantly, Conway possesses a trait that is, in its own way, just as quintessentially American as the frontier virtues: he’s an evangelist. He learned how to live on his own in the woods, merging with “the high art and godliness of nature,” and he has devoted himself to spreading this message: You can, too.

If Conway were in fact living alone in the wilderness, his loneliness would make more sense. Instead, he’s spent much of his life proselytizing, urging people to give up an existence swamped in “smog, plastic, and a never-ending babble of nonsense enough to scramble brains, raise blood pressure, create ulcers and sponsor heart disease” to live in the woods. Gilbert testifies to his charisma in preaching this doctrine; she’s seen him captivate a roomful of rowdy high school students and “the scariest posse of drug dealers you’d ever want to meet” in New York’s Tompkins Square Park.

Conway makes money speaking to classes of schoolchildren and at county fairs, gives interviews to the press and takes on apprentices at Turtle Island, his camp, where he teaches young people how to live off the land. He’s had a series of beautiful, strong, capable girlfriends and many worshipful disciples. And yet these people, no matter how much they may idolize Conway at first, have a way of getting fed up and walking out on him. Despite his heartfelt desire for a wife and children, he has neither.

“The Last American Man” is Gilbert’s attempt to sort out how someone who embodies so many qualities she cherishes and admires, a man who is “our mythical inner self made flesh,” can be so impossible. She clearly likes Conway, but harbors few illusions about his ability to manage what she calls “a showdown between the two things he craves most: absolute love and absolute control.”

The daughter of back-to-the-land counterculture types herself, Gilbert has had a lifelong crush on cowboys that she’s got just enough sense to make fun of but perhaps not quite enough to get over. After graduating from college, she ran off to a ranch in Wyoming where she told people she was from “Lubbock, Texas” (it was really Connecticut) and persuaded the other “wranglers” to call her Blaze. It was there that she met and romanced Eustace Conway’s “damn cool” younger brother, Judson, a less austere, more ironic variation on the Man himself.

But for the pop culture cowboy of Gilbert’s fantasies, “women are for rescuing and also for tipping your hat to as you ride off into the sunset without them.” Eustace, with his dream of heading up a large family (he told one girlfriend he hoped to father 13 children by her), probably bears more of a resemblance to the real-life pioneers, and his chief problem is a lack of pioneer women. “What he really needs is a woman who is both strong and submissive,” Gilbert decides, thinking of Daniel Boone’s long-suffering wife, who raised 10 children of her own and eight orphans in rustic forts and nearly left her husband after getting a brief taste of comfortable settlement life while he was out founding the colony of Kentucky.

Ultimately, Rebecca Boone followed her husband back to the frontier. But then again, she didn’t have much of a choice — that’s what a wife did 200 years ago — and she was miserable. The thrilling masculinity practiced by Boone and other frontiersmen, it turns out, was founded on the principle of bossing everybody else around and getting no back talk about it, either. Why would anyone want to live with that who didn’t have to? And what happens to the patriarch when suddenly there’s no more patriarchy, when everybody who doesn’t like playing by his rules decides to take the ball and go home?

Of the dozen or so smitten women who have joined Conway in his woodland retreat (including one who wrote him passionate letters addressed to “My Primitive Savage Pagan”), not one ultimately could find a reason to put up with his demanding, tyrannical ways. “I desire you still,” an Apache doctor wrote him. “You are a charmer. But I feel you want me for your needs … as a glorification for you.” Another described him as “loving but intolerant” and obsessed with accumulating more land for Turtle Island. “It got to the point where I never saw him. The only time we spoke was when he gave me orders.” This is a woman who characterized her move to the woods as “following my bliss” and “a spiritual mission”; she didn’t sign up for boot camp, and she didn’t stick around for it, either.

Likewise, Conway’s apprentices, the people he hoped would fan out across the nation and spread the word, tend to leave Turtle Island in rage and disappointment, complaining “you make me work so hard … make me feel unworthy … I feel unappreciated and unwanted.” He, in turn, sees himself as unsupported and misunderstood by overgrown spoiled children too accustomed to being indulged. “I have worked very hard to make this place what it is,” he wrote in his journal. “What have they done? What investment have they ever made in anything that is a challenge? How am I to put up with them?”

“How am I to put up with them?” maybe be one of humankind’s primordial questions, but it’s particularly plaintive coming from someone whose ambitions — leading a transformation in the American way of life, heading a large family — entail the active, enthusiastic participation of other people. Conway can teach a child that “the woods are alive” by having both of them buried in the ground with only their faces sticking out (“Now we are the forest floor … and let’s tell the others what we see and feel”), but he hasn’t a shred of empathy for acolytes who are dismayed when they slave for him all day long only to be relentlessly criticized — even though he himself suffered exactly the same, painful treatment at the hands of his own perfectionist father. A frustrated outdoorsman turned chemical engineer, the brilliant but pitiless Eustace Conway Sr. would subject his son to humiliating mathematics drills at parties (it was the one subject Eustace the younger never quite mastered) and made a habit of calling him an idiot.

There is so much pining in this book: Conway longing for a bride he can respect who will then put up with being treated disrespectfully; his followers craving a very contemporary kind of fulfillment from a man bent on rejecting modern life; and finally Conway’s women and Gilbert herself, infatuated with a vision of earthy, elemental, self-sufficient manhood who turns out to be just another damaged guy trying to shake off the legacy of a remote, unloving father. Even for someone who can get into the idea of living in a world without Lester Young saxophone solos or Ernst Lubitsch movies, this must seem pretty dire. And needless to say, if Conway ever manages to have those kids, they’ll probably be basket cases, too; “I’d be there from the beginning to teach them what’s acceptable and unacceptable behavior,” he says when contemplating his still-hypothetical brood.

If “The Last American Man” is a book about not wanting to live with such a man, Noelle Howey’s memoir, “Dress Codes,” is about not wanting to be one. Howey’s father is a transsexual, a closet cross-dresser who decided, when Noelle was in her late teens, to live as a woman and, eventually, to have gender reassignment surgery. Howey sees “Dress Codes” as a story about how to become a woman, paralleling her own coming of age (including a battle with clinical depression in graduate school) with her father’s transformation into a woman and her mother’s emergence from the decades-long funk of an unsatisfying marriage.

But “Dress Codes” is also about the misery of being a man, as experienced by Richard Howey, Noelle’s father, whose life story is woven into his daughter’s. Of course, it’s especially unpleasant being a man when deep inside you really want to be a girl, but what’s remarkable about the version of manhood Richard adopts is how much he winds up resembling Eustace Conway’s father, Eustace Conway Sr. Both men are emotionally withdrawn and domineering. Both subject their families to a stream of withering criticism. Both seem marinated in a thin, bitter broth of resentment.

In a passage of “Dress Codes” devoted to the youth of Noelle’s mother, Dinah, a group of teenage girls talk about whether they’d ever want to be boys. “Boys have terrible lives,” says one. “They have no friends.” Dinah silently concurs: “Boys were barely even sociable. The nice ones sat quietly and didn’t say much, and the ones who did speak didn’t usually have anything pleasant to say. Dinah couldn’t imagine having to live in such a solitary world.” Later, the pubescent Noelle will avoid her surly father, terrify herself with visions of imaginary rapists and, when she finally leaves home, seek out a boyfriend as faultfinding as her dad and beg him to call her degrading names in bed.

“When he was still male,” Noelle writes of her father, “I had a dad possibly like yours: sullen, sporadically hostile, frequently vacant. I had a dad who became a woman in order to be nice.” It wasn’t until her father began his transformation that the two could finally communicate. “Dress Codes” concludes with a scene of Noelle and her parents gathered together for her birthday: “It was a simple family dinner — three women: a father, a mother, and a daughter — and that was the greatest part about it … We had achieved the mundane … In the end, there was just camaraderie, affection and what truly counts as unconditional love.”

It’s just that to get there, Richard has to have his penis removed and change his name to Christine. There’s got to be a less drastic way to get rid of the pioneer spirit — or whatever it is that makes these guys such a drag to live with and ultimately so lonely. Given what a glum assignment it turns out to be, no wonder Eustace Conway is the last American man.

Of course, we’ve all been taught by now that a transsexual like Richard Howey was a woman trapped in a man’s body, and how can such a person, when so thwarted, be happy enough to have warm familial relationships? But it’s also worth noting that “The Last American Man” ends with a scene in which Conway whoops ecstatically at a splendid buck walking with his doe and fawns on a dark country road, “I love you! You’re beautiful! I love you!” Gilbert intends the moment to stand for Conway’s robust embrace of nature, but I couldn’t help thinking that the buck has his family, and even Noelle Howey’s very unconventional father has hers, while Conway is once again standing in the dark, proclaiming his affections to yet another creature that’s preparing to run away from him.

In this breezily appealing first novel, Elizabeth Gilbert presents us a heroine as smart, sly, plucky and altogether winning as her own prose; it’s difficult, in fact, not to develop a knee-weakening crush on both. At the age of 18, Ruth Thomas has hair so black and thick “she could sew a button on a coat with it”; her face is roundish, with an “inoffensive nose,” and though she’s saddled with “a bigger rear end” than she’d prefer, she pays it little mind, for she’s not, as Gilbert writes, “that kind of girl.”

Elizabeth Gilbert has made her reputation with her nonfiction magazine articles. Now, with the stories in “Pilgrims,” she proves herself a capable, if at times uneven, fiction writer too.

Gilbert’s favorite theme in both genres is women in the land of men, but in covering this terrain in fiction, she bows a bit too deeply before the macho shrine of Papa Hemingway. Consider the title story, with its fertile premise that Buck, a young cowboy, has a crush on Martha, an alluring Eastern girl hired to work on his father’s ranch. At the story’s climax, Buck and Martha sit before a campfire, having led a group of Sunday hunters on an elk shoot in the mountains. “Talk about a bunch of pilgrims,” Martha comments. “These guys have never even been in a backyard.” She and Buck of course are also, as the story hints a bit too insistently, on unfamiliar territory. Here’s a key moment, narrated by Buck: “She handed me the bottle again, and this time I drank. We did not talk for a long time … and when the fire got low, Martha Knox put more wood on it … In October up there it isn’t easy to be warm and I would not pull away from that kind of heat too fast.”