“The Search for Everything” is a tender and smarting breakup record, presumably about the end of Mayer’s relationship with the pop star Katy Perry. PHOTOGRAPH BY RYAN PFLUGER / THE NEW YORK TIMES / REDUX

On a recent trip to Cuba, a travelling companion and I found ourselves in a strange make of Honda, being piloted through the verdant countryside by a twenty-four-year-old university professor named Ernesto. We’d met him through an enterprising employee of our hotel in Havana. For a prearranged price, Ernesto had agreed to ferry us from the city to Viñales, an inland mountain town known for its vistas, tobacco plots, and horseback-riding trails. These sorts of transactions are commonplace in Cuba, where the economy tolerates (if not quite allows for) a second, shadow marketplace: indulging the whims of insistent tourists. Ernesto stayed abreast of American culture primarily via a flash drive containing television shows and pop songs, which was floated over weekly with new files from Miami. The particulars of the drive’s transport and arrival remained obscured to me. Ernesto liked Jimmy Kimmel, he said, and cooking shows. Mostly, though, he was into the songwriter and guitarist John Mayer.

On the three-hour drive to Viñales, we listened to Mayer’s 2002 single “Your Body Is a Wonderland” several thousand times. Rather than unbuckling my seatbelt, opening the door, and allowing my body to slowly roll out of the car and onto the hot pavement, I took this to be simply another part of my Cuban experience, like scratching off endless, non-functional Wi-Fi access cards, or drinking two-dollar mojitos at noon. Earlier that day, from the back of a bicycle taxi bouncing across Havana, I had seen both a disembodied pig’s head and a small dog scampering down the street in a hat and sunglasses. I could not pretend to understand anything.

“Do you like it?” Ernesto turned to ask me, his mirrored sunglasses glinting. We were on play five or six of “Your Body Is a Wonderland.” I was seated in the front of the Honda. I paused for a beat too long. He laughed. “O.K. What do you like instead?”

This was a very fair question. Yet I found it impossible to answer. I scrunched my face. “Bob Dylan?”

Ernesto nodded sagely. “His lyrics are better. This—it’s all girls and stuff, I know.” Still, he did not feel compelled to clarify his loyalty.

It’s reasonable to describe the pop critic’s job as the identification and illumination of certain aspects of culture—to sniff out how and why a song or sound becomes omnipresent, beloved. The more cynical among us might wonder if many of these ascents toward ubiquity are not in fact preëngineered by corporations, but I don’t think the global psyche is quite so easily cracked. The given yearnings of a culture are too mysterious to be accurately foreseen. Yet, if you think hard enough about why a song is working on people, its value usually becomes clear.

Every once in a while, though, I am so flummoxed by a popular artist’s appeal as to be rendered agog. Since 2001, Mayer’s syrupy soft rock has been a staple of American pop radio, particularly the stations that play in pharmacies and waiting rooms, or anywhere there is a stretch of unfashionable carpet. He noodles intricate riffs on an electric guitar while singing moony platitudes in a breathless voice, as if someone has just struck him in the midsection with a golf club. His face contorts into various iterations of the open-mouthed “Home Alone” shriek while his hands move deftly about the frets of his guitar. He is a very good musician and, by all accounts, an inventive if sentimental songwriter. For some reason, the whole thing makes me think of hard-boiled eggs.

Mayer has seven full-length albums, including his most recent, “The Search for Everything,” which he has so far issued in two four-song “waves,” an extravagant word for “chunks.” (The second “wave” arrived last month, while the third and final “wave,” which will contain six songs, is expected in April.) Later this spring, Mayer will play a sold-out show at Madison Square Garden. For a stretch, the tabloid press delighted in portraying him as a demon wearing a Rolex, breaking hearts willy-nilly. Photos of Mayer looking caddish and smug were placed adjacent to photos of famous women crying or looking otherwise stricken, with headlines like “Girls Who Date John Mayer Always Regret It!”

It is difficult to say whether any of those accusations were fair. “The Search for Everything” is a tender and smarting breakup record, presumably about the end of Mayer’s relationship with the pop star Katy Perry, whom he has dated on and off since 2012. Many of his new songs address, sometimes obliquely, a fear that he mishandled a gift, and accidentally sentenced himself to a life of sexual excess and emotional quarantine. On “Roll It On Home,” an amiable country song buoyed by pedal steel, he soothes his worry after a night of drinking. “Tomorrow’s another chance you won’t go it alone,” he assures himself.

Like anyone going through the dissolution of an important relationship, Mayer oscillates endlessly between blustery self-confidence and utter devastation. On the slinking single “Still Feel Like Your Man,” he broadcasts his worth, his voice slipping in and out of falsetto: “The prettiest girl in the room, she wants me, I know because she told me so,” he sings. Who is this dude kidding? He misses his girlfriend. “I still keep your shampoo in my shower in case you wanna wash your hair,” he admits.

The album is also about getting older (Mayer will turn forty this year) and the fears and insecurities we manage to shrug off if not neutralize en route. Age offers us nothing if not the cathartic reassurance that there’s never an easier way; meeting the needs of others (and letting them meet our own) is always hard. Still, Mayer wonders, over and over: What if you lost the thing you wanted because you weren’t ready then, but you’re ready now? “Moving on and getting over, I’m not the same, it seems to me,” he sings. “I’m one text away from being back again.” It’s hard to know if Mayer means regressing to a younger, less enlightened version of himself, or regaining access to the woman he loved and lost. Regardless, the animating tension of “The Search for Everything” is in the way his finger quivers above that “send” button. Our spiritual victories, they are always tenuous.

These days, the twenty-six-year-old British pop singer Ed Sheeran is Mayer’s most obvious musical acolyte. Sheeran’s recent single “Shape of You,” which has reached No. 1 in thirty countries, is a lithe and lascivious update of “Your Body Is a Wonderland.” Both songs are uncomfortable salutes to the female form, though Mayer was more mawkish in his recounting of the pleasures of flesh. (“One mile to every inch of / Your skin like porcelain / One pair of candy lips and / Your bubblegum tongue,” he moans.) Sheeran’s advances, at least, are met by a woman who appears as ready as he is: “Boy, let’s not talk too much, grab on my waist and put that body on me,” he recounts her saying. The thrust of the chorus is simple: “I’m in love with your body,” Sheeran repeats.

In 2010, Mayer gave dumb and aggressively ribald interviews to_ Rolling Stone_ and _Playboy _(in the latter, he suggested that his sexual organ is a white supremacist, then jokingly used a racial epithet), prompting a two-year hiatus in which he retreated to Montana, started wearing a large hat, and grew his hair out, a series of prostrations that felt, then and now, like an absurd bid for public forgiveness. Prior to that break, he dabbled in standup comedy and, for a while, was a welcome recurring player on “Chappelle’s Show.” (In one skit, he attempted to cajole white people into dancing by playing electric-guitar riffs.) Yet his songs remain so tepid and staunchly edgeless as to suggest an irreconcilable chasm between art and artist. It’s as if Mayer is so cowed and discombobulated by sexual attraction that he devolves—becomes a dopey, formless version of himself. It is incredibly hard to imagine that the narrator of these songs—a man so consistently overwhelmed by the very fact of women—has ever been friends with one. In “Daughters,” a single from his second album, “Heavier Things,” he describes the arc of a woman’s life as, “Girls become lovers who turn into mothers.” That he is concerned, suddenly, by the shallowness of his own relationships and what they have wrought for him feels unsurprising.

Yet “The Search for Everything” is also Mayer at his most human. Though he has been self-effacing before (he quietly released two albums during his retreat from the spotlight, “Born and Raised” and “Paradise Valley,” both of which contained mea culpas of a sort), his new songs feel like a reckoning. The type of longing he expresses here—for a tether, a person he can’t forget, a counterweight to the strange winds of celebrity and to the freedom that comes with making a bunch of money—isn’t easily satisfied, or admitted. And it’s here where I can finally see (and easily) what Mayer might offer his listeners: how to slog through regret, and find hope.