Because life has to be lived forwards but can only be understood backwards, as Kierkegaard says, we sometimes come to realize what we truly want from it—whom to marry, which vocation to pursue—after that knowledge is well past its use-by date. The Irish writer Colm Tóibín has made a specialty of such deferred recognitions. In Nora Webster (2014), perhaps his finest novel, the recently widowed heroine, a mother of four in 1960s Ireland, has lived a life of duty and self-sacrifice. When she begins to cultivate a love of music, neglected while her husband was alive, it represents the start of an awakening. One night, at a gathering of the local gramophone society, Nora is presented with an album of Beethoven’s piano trios. The cover has a photo of the players. Gazing at it, she’s struck by the young cellist (“blonde and faintly smiling, with a strength in her face”) and suddenly feels that “she would give anything” to be her. As the music starts to play, it occurs to Nora, who is closing in on fifty, “how easy it might have been to be someone else, that having the boys at home waiting for her, and the bed and the lamp beside her bed, and her work in the morning, were all a sort of accident.” Desire may be a portal to a larger, richer life, but it can also bring us up against the lives that got away.

A lot depends on who’s doing the desiring. Unlike Nora Webster, whose humble background limits her horizons, the fictionalized Henry James at the center of The Master (2004) has both the talent and the wherewithal to make himself an artist. “Everyone he knew carried with them the aura of another life which was half-secret and half-open, to be known about but not mentioned,” Tóibín writes of James, whose attunement to the thwarted dreams of others is a key to his creative gift. As a closeted gay man, James has his own secret life. In one poignant episode, the fifty-something author imagines setting up house with Hendrik Andersen, an ambitious young sculptor he met in Rome. A few months later, when Andersen visits him at his house in rural Sussex, it’s made clear that this daydream will remain just that. The saddest moment comes when Andersen inspects the shelves in James’s study and realizes the books they hold were all written by his host. “Did you not once plan it all?” he asks excitedly. “Did you not say this is what I will do with my life?” James can only turn away, his eyes full of tears. Compared with what he might have had and done, his actual biography seems suddenly, like Nora Webster’s, “a sort of accident,” his art a consolation prize.

Tóibín’s most concentrated study of the missed or canceled life comes in his next novel, Brooklyn (2009). Eilis Lacey, its protagonist, is a young woman from the town of Enniscorthy, in southeast Ireland, where much of Tóibín’s fiction is set. It’s the early 1950s, and economic torpor has people rushing for the exits; by the decade’s end some half a million would depart in search of brighter prospects. Eilis, who works for meager wages in a local grocery store, has no plans to join the exodus until an offer arrives from a kindly priest in Brooklyn. Father Flood, an Enniscorthy native, presides over a church in an Irish enclave of the borough, where he promises to find her a better-paying job. In James’s Portrait of a Lady, Isabel Archer leaves America for Europe with the intention of “affronting her destiny.” Eilis, whose story is a canny recasting of Isabel’s, is less intrepid. She is comfortable enough in her hometown, where she has always imagined she would spend her life, “knowing everyone, having the same friends and neighbors, the same routines in the same streets.” But her personal wishes are irrelevant. Her widowed mother and single older sister seem in favor of the move, and so she goes.

Brooklyn takes some adjusting to. Eilis excels at her department store sales job and discovers untapped depths of resilience, but the American life she starts to build feels painfully provisional. This feeling only intensifies when she meets a young plumber named Tony Fiorello at the weekly parish dance. Tony, the son of Italian immigrants, is decent and adoring, if perhaps a little bland. When he declares his love and starts to mention children after just a few dates, Eilis grows wary: “His saying that he loved her and his expecting a reply frightened her, made her feel that she would have to accept that this was the only life she was going to have.” For the first time Eilis seems to recognize not only that other lives are possible but that she may have some agency in bringing them about. Instead of telling Tony that she loves him too, she abruptly says good night. It’s a gesture of independence but one that’s difficult to sustain in the days that follow:

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She could think of no good reason to tell him that she wanted to see less of him. Maybe, she thought, she should say to him that she did not want to talk about their kids when they had known each other only a short time. But then he might ask her, she believed, if she was not serious about him and she would be forced to answer, to say something. And if it was not fully encouraging she might, she knew, lose him. He was not someone who would enjoy having a girlfriend who was not sure how much she liked him.

Quoted in snatches, Tóibín’s prose may seem like nothing very special, but listen closely and it crackles with a sublimated longing. “I think some of it is fear—a fear of tone, that it’s got to be held in, that anything more would involve some sort of release,” Tóibín has said by way of explanation for his pared-back style. “There’s an element of feeling that if I try to write a longer sentence, I will actually lose control.” This might serve equally well as a description of Eilis, who has learned to master her emotions, to refract and rechannel them, lest they displease the people whose protection she relies on. See how in the passage above she keeps confusing her feelings with the feelings of others. A simple sentence like “She could think of no good reason to tell him that she wanted to see less of him” carries the suggestion that her own preference is not, to her mind, a good enough reason. What ultimately leads Eilis to accept Tony’s advances is the same thing that brought her to Brooklyn in the first place: a habit of obedience, a desire to please.

Tony, to be sure, is no Gilbert Osmond, the emotional tyrant whom Isabel ends up with in The Portrait of a Lady, but he does have a possessive streak. When Eilis learns that her sister has died back in Ireland, he insists that they marry before she goes home. Once she gets there, however, she finds her mother so undone by grief that she doesn’t have the heart to tell her what’s happened. The omission takes on a new dimension when Eilis is set up with an eligible young local named Jim Farrell. Her plan had been to visit Enniscorthy for just a few weeks, but as her attachment to Jim deepens she begins to feel the pull of a repatriated future. When a nearby factory offers her a bookkeeping job, a profession she’s been studying at night school in Brooklyn, the appeal only grows.

For the locals, Eilis has been brushed with an American glamour, and it isn’t just her exotic tan or fashionable clothes. “Everything about you is different,” her old friend Nancy Byrne says admiringly. “You have an air about you.” For Eilis, Enniscorthy has been reenchanted by her time away—and by the new esteem she’s held in. The life she can imagine living there would be a life of her own choosing, but it’s a choice she never gets to make. A local busybody learns about her marriage and threatens to expose her, forcing Eilis to return to Brooklyn, like Isabel going back to Osmond at the end of James’s novel. Timing, we’re told, is the secret to comedy. For Tóibín, it turns out to be the secret to tragedy as well.

Brooklyn left Eilis on the threshold of her new American life. In Long Island, Tóibín’s latest novel, that life has reached another threshold. More than twenty years have passed, and Eilis has migrated once again, this time from the city to the suburbs. She and Tony and their two teenage children, Larry and Rosella, are living in Lindenhurst, on Long Island, in smothering proximity to Eilis’s in-laws. Because the Fiorellos have never quite accepted her, she receives a lot of hostile scrutiny but without the consolation of belonging. A stray remark about the war in Vietnam, where she fears that Larry may end up, is enough to cause a small domestic scandal. “I can’t think of anything that would make me more proud,” fumes Tony’s reactionary father, while Tony, a browbeaten son, says nothing to support her. Such unfriendly surroundings have made of Eilis a kind of inner émigré.

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The situation goes from adverse to intolerable when she learns that Tony has a mistress. What’s more, the mistress is now pregnant. “If anyone thinks I am keeping an Italian plumber’s brat in my house and have my own children believe that it came into the world as decently as they did, they can have another think,” the woman’s aggrieved husband tells Eilis during an unannounced visit. Eilis, understandably, doesn’t want the baby either. When Tony and his family signal their intention to adopt the child anyway, she votes with her feet and returns to Enniscorthy, where her elderly mother still resides. How long she plans on staying there is anybody’s guess.

A sequel is a second chance, for both a writer and his characters. Jim Farrell, with whom Eilis has had no contact in the intervening years, remains unmarried, living alone above the Enniscorthy pub he inherited from his parents. Eilis feels an abiding shame at the way she jilted him in her youth, and Jim, whose perspective we inhabit for stretches of the book, has never quite recovered. When he learns that she’s in town, he begins to wonder what might still be possible. Eilis has had the same thought, and the two of them are drawn inexorably together. There’s just one catch: Jim is engaged to Nancy Byrne, Eilis’s old friend, who was widowed some years earlier and now runs a chip shop. Until Eilis showed up, Jim had been content with her. Now she comes to seem like an impediment to happiness.

Brooklyn is emphatically designed, full of pointed symmetries and ironic reversals, and yet it never feels contrived. Line by line, the writing is so textured and immersive, so hypnotically even-keeled, that we rarely anticipate where Tóibín is leading us. Long Island, though it has moments of great pathos and drama, is a more predictable novel, at once overplotted and artistically undercooked. A lot happens in its three-hundred-odd pages, but not enough of it seems to matter. It’s in part because so much happens, the crises coming thick and fast, that the book ends up feeling so weightless. But it’s also a product of the changing times in which the story is set.

Lindenhurst and Enniscorthy were hardly epicenters of the sexual revolution, but its aftershocks are palpable in the world of Tóibín’s novel. However slowly, the pressures of social conservatism—religious observance, old-school propriety—have begun to ease, and new truths are now speakable. The conversation Eilis has with Larry about his father’s affair would have been plainly impossible in Brooklyn:

“There is a woman who is going to have a baby and Dad is the father.”
“She is his girlfriend, then.”
“She is not and never was. He was doing a job at her house.”
“And they are having a baby together?”
“She is having the baby.”

For a novelist who thrives on silence and evasion, this new forthrightness is clearly not ideal. In a circumscribed milieu, the slightest breach of etiquette may carry outsize consequences. In a more liberal atmosphere, transgression is less meaningful, as we see in Long Island. Though Eilis and Jim are at pains to conceal their liaison from the rest of Enniscorthy, they speak to each other with an openness that’s rare in Tóibín’s work. “Times have changed,” he tells her. “I see that in the pub. Things were different when we were young. But I’ve often regretted that we never spent a night together. I wish we’d done that.” He then suggests a meeting place in Dublin (“It’s a modern hotel, sort of anonymous”) where they might make up for lost time.

There is something thrilling about this candor, coming as it does after years of separation, but isn’t it also just a touch generic? What made Brooklyn so quietly audacious was Tóibín’s choice of a passive heroine and the subliminal dramas he devised for her. Consider the following moment from that book, in which Jim and Eilis, on a day trip with a couple who are trying to set them up, go swimming in the ocean:

As she wallowed there, staring at the blue sky, kicking her feet to keep herself afloat, Jim approached her but was careful not to touch her or come too close. When he caught her eye, he smiled. Everything he did now, every word he said and every move he made, seemed deliberate, restrained and well thought out, done so as not to irritate her or appear to be moving too fast. And almost as an aspect of this care, he made his interest in her totally clear.

Such prose functions as a kind of screen through which a character’s occluded desire is seen only in suggestive outline. When there’s nothing to conceal, though, the usual brilliant plainness of Tóibín’s writing can slacken into mere banality.

This is too often the case in Long Island. “I need you to spell out what your intentions are,” Eilis tells her mother-in-law near the start, and there is much spelling out in the pages to come. “I’ve drawn up plans for the kind of bungalow we might build,” Nancy says to Jim at the very moment he’s begun to dream of running off with Eilis. The irony is hard to miss, and yet Tóibín continues: “She, he saw, was living in the future. Her life was made up of plans.” And then, just for good measure: “He was in the future too. He dreamed of coming home from work in some American suburb, pushing the gate and opening the front door to find Eilis there.” Page after page is consumed by such expository filler, though the dialogue can be just as crude. At one point Eilis asks Jim to meet her on the beach, the one described in Brooklyn, where they reminisce about that distant afternoon:

“All those years ago,” he asked, “when we danced together and saw each other, were you thinking about, you know, the fellow in America, the one you are married to, and were you looking forward to seeing him?”
“That’s the longest question you’ve ever asked me.”
“What’s the answer?”
“I was confused,” she said.
“Are you confused now?” He deliberately kept his voice soft and low.
“No.”

This time, Eilis seems to know exactly what she wants:

“Are you going to ask me?” she began.
“What?”
“Why I phoned you this morning and not some other morning.”
“I’m asking you now.”
“I got news from home and it made me realize that I don’t want to stay married to Tony. But there are complications and I need to let you know about them.”

For the reader, if not the couple themselves, the thrill is gone. Now that they can tell each other how they really feel, the fog of enriching implication that once clung to their meetings has dispersed. What we’re left with is a largely subtext-free exchange of propositions and avowals.

Largely but not completely. To be fair to Tóibín, these declarations come later in the book and are preceded by a fair amount of pregnant indirection. For all the easing of old strictures, there remains plenty that goes unsaid. In Brooklyn, it’s Eilis who can’t bear to tell Jim about Tony; now, in one of many inversions, it’s Jim who can’t bear to tell Eilis about Nancy. No one in Enniscorthy knows of their engagement. But there’s a difference between these two silences and the way they function in each novel.

When Eilis neglects to mention her American marriage in Brooklyn, it feels like an organic consequence of her straitened social world. Jim’s omission in the sequel, by contrast, is more a matter of narrative expedience. For the plot to work, Eilis must remain in ignorance of Nancy’s relationship with Jim, and vice versa. That this is what happens, despite several lengthy catch-ups between the two old friends, asks a lot of the reader’s credulity. At one point Nancy learns that Jim, a creature of routine, has gone to Dublin unexpectedly on the same day that Eilis also happens to be there. Even though he’s unable to explain the reason for his trip, Nancy lets it slide.

In his essay “The Art of Fiction,” Henry James asks, “What is character but the determination of incident? What is incident but the illustration of character?” This indivisibility is an aesthetic ideal that Tóibín fulfills in much of his work but falls short of in Long Island, where character can seem like a mere pretext for incident, and where incident, rather than illustrating character, often simply flattens it. The more he relies on Nancy’s guilelessness to keep the plot in motion, for example, the more implausible that guilelessness comes to feel.

In his poem “High Windows,” a forty-something Philip Larkin peers in from the outside at the erotic funhouse of the Sixties:

When I see a couple of kids
And guess he’s fucking her and she’s
Taking pills or wearing a diaphragm,
I know this is paradise
Everyone old has dreamed of all their lives—

Bonds and gestures pushed to one side
Like an outdated combine harvester,
And everyone young going down the long slide
To happiness, endlessly.

Long Island is another work in which the “bonds and gestures” of an earlier time are being “pushed to one side,” clearing the way for a libidinal bonanza. Tóibín, by all accounts, got to experience that bonanza firsthand. Born in Enniscorthy in 1955, he reached adulthood at the apex of the sexual revolution. “Barcelona, 1975,” a short story from 2005, is a description (“entirely real,” Tóibín has said) of the first gay orgy he took part in. At the time, though, he found his immediate surroundings unsuitable for fiction. The problem, he found, was that the literary and artistic worlds of late-Seventies Dublin, where Tóibín was working as a journalist, lacked an established set of manners. “You couldn’t have a dinner party,” he has said, “because someone would get really drunk, the food would burn—it would be awful in some way—and trying to dramatize it would itself be futile.”

It was only when he tried to write about the past that he found what he was looking for. His first novel, The South (1990), about another Enniscorthy woman who leaves Ireland in hopes of finding a fuller life abroad, was originally set in the 1970s. When Tóibín moved the story back a generation it acquired a new density and texture. “Once I went back in time,” he said, “I was at home.” It’s true that some of his novels are set closer to the present—The Story of the Night (1996) takes place in Argentina between the late 1970s and early 1990s, The Blackwater Lightship (1999) in Enniscorthy in the early 1990s—but, crucially, these books are about the lives of gay men, for whom discretion remained imperative well after the heyday of free love. Long Island is unique among Tóibín’s novels in taking as its subject a straight romance in an age of incipient sexual freedom. It doesn’t seem an accident that it fails to reach his usual high standards.

Needless to say, many writers have prospered on the same permissive ethos that Tóibín finds so inimical. Sally Rooney’s Conversations with Friends (2017), to take an example from one of his compatriots, is another book about an emotionally wounding love triangle. When the young narrator gets entangled with an older couple in a sort-of-open marriage, it’s precisely the absence of an established set of manners, of clear rules dictating what’s permissible, that makes the action so enthralling. As its title suggests, the book is full of talk. Almost nothing goes unsaid between the main characters, who are strong believers in the value of directness, but directness, which creates as many problems as it solves, gets them only so far.

Like the speaker in “High Windows,” the characters in Long Island are caught between two worlds while reaping the benefits of neither. The same could be said of the novel itself, which lacks both the aching reserve of Tóibín’s earlier work and the tumultuous frankness of his younger contemporaries. Still, for all its faults, the book manages to capture something of the pain of missing out, as well as the way an idealized counterlife—the “paradise,” to use Larkin’s word, where we were never admitted—can make our actual lives seem rather paltry by comparison. As the novel approaches its finale, it seems like the would-be couple will miss out once again. Jim’s secrecy over his engagement proves disastrous, and it’s a testament to Tóibín’s narrative gifts that the disaster, when it comes, is as affecting as it is. The cruelest aspect of the ending, but also the most powerful, is the way that hope remains alive. “If the phone rang in your garage on Long Island one morning, or one day, and it was me and I was in New York, or was even closer, and I had come to see you, what would you do?” Jim asks in a moment of desperation. Eilis, for a change, says nothing, and her silence, which lingers after the final page, keeps the two of them suspended in a state of tormenting possibility.