Dan Wakefield Needs A Ride

The bestselling author made a late-life return to the hometown that angrily rejected him as a young man, after his greatest literary success. And in an ironic twist worthy of a novel, the city heartily embraced him at a time in his life when, perhaps, he needed it most. But does Indianapolis really want the complete, unabridged Dan Wakefield—or just the CliffsNotes?

Editor’s Note: In fond remembrance of Dan Wakefield on the occasion of his death, Indianapolis Monthly is revisiting the works of and about the famed Indianapolis writer, reporter, and prodigal son. The original story was published on our website on January 3, 2017.

If you know Dan Wakefield long enough, chances are, sooner or later, you will give him a ride.

The author, now 84, gave up driving several years ago when he still lived in Miami Beach, before he retired his faculty position at Florida International University and, in 2011, moved to Indianapolis, back to the city where he grew up and found a setting for the novel that would give him his greatest literary fame.

The story of that homecoming should be deeply satisfying to anyone who appreciates a strong narrative arc, which goes something like this: Wakefield’s sardonic and sexually explicit breakout book about Indianapolis, Going All the Way, also made him a pariah here, until time healed old wounds on both sides, and he could finally return, triumphant, to cement the literary legacy long overdue him. File under “Late, It’s Never Too.”

Like any good plotline, however, this one has twists. Miami Beach was an ideal locale for a senior man without a car, the kind of place a guy is supposed to retire to, not from. Wakefield resided in the heart of South Beach, on the ocean, in a walk-up apartment between 3rd and 4th streets, near the 5th St. Gym, where Muhammad Ali used to train. “He lived, in his mind, the perfect life—it was like being in New York City, only on the beach, in terms of the convenience and the urban feel of South Beach, and he loved being able to walk,” says author Les Standiford, who hired Wakefield into Florida International’s creative-writing program. “That’s the hotspot, the nerve center, of South Beach. One of his favorite spots was the News Cafe, up on 8th Street, and he would go out, get a coffee, get a paper, take some air, and then he’d be back working at his desk until the late afternoon or evening,” continues Standiford. “I think he was in heaven. That’s the sense I got. He was living the dream.” 

Nevertheless, in 2011 Wakefield gave up the sweet life in South Florida for a book project in New York. A day after Wakefield moved to the city, the book’s subject bailed. And the author, who has mythologized his time living in Greenwich Village in the 1950s, “did not find New York as pleasant as he remembered it,” says Standiford.

Wakefield keeps pat stories in his pocket for questions he has to answer a lot. Not rehearsed, exactly, but kind of practiced through repetition—material. How did he end up back in Indianapolis? Well, he accepted a 2011 invitation to speak at the Kurt Vonnegut Memorial Library, after he’d edited a book of the author’s letters. On the suggestion of noted Indianapolis architect Evans Woollen, whose sister Wakefield had dated in high school, Wakefield stayed in the home of librarian Cathy Gibson, a mutual friend. Gibson threw a dinner party for Wakefield while he was in town for the Vonnegut Library engagement, and Wakefield knew one of the guests, Jane Rulon, former head of the Indiana Film Commission, from when the film version of Going All the Way was shooting in Indianapolis. “Listen,” Wakefield said to Rulon, “what about—could you take me around Sunday to look at apartments downtown?” So they drove Indianapolis in Rulon’s car until they passed an old downtown building that looked suitably bohemian in Wakefield’s estimation, and he eventually moved in.

That’s how he usually tells the story, more or less.

But beneath the high-flown romantic appeal of Wakefield’s decision to return, down at street level, if you will, lay the practical considerations, which were—considerable. For a man of advanced years who doesn’t drive, even one as well-traveled as he (the writer has lived in New York, Boston, and Los Angeles, as well as Miami), the prospect of resettling must have been pretty damn daunting. Indianapolis is a notorious car town where even most of the inner city feels like a sprawling suburb. Unlike Miami Beach, here, a guy might walk for miles just to reach a bus stop, let alone an actual destination, and freeze his ass off doing it. Wakefield was unmarried, had no children. His few relatives in Indianapolis were aged as well, and many of his close friends here were schoolmates from Shortridge High, also getting on.

More than just returning, Wakefield was, in a way, throwing himself on the mercy of the city that once rejected him.

Not long after Wakefield moved to Indianapolis, Travis DiNicola, then director of Indy Reads and cohost of the radio program Art of the Matter, was driving down Massachusetts Avenue, and he saw Wakefield on the sidewalk. He had met the author a few times at fundraisers and other goings-on, and the two were friendly acquaintances. “He basically waved me down,” says DiNicola, “because he needed a ride. He recognized my car.” DiNicola and Wakefield soon became dear friends. “So it was at that point I became one of about a dozen people in Indianapolis who are Dan’s drivers.”

For a few months last year, I was one of those dozen or so people as well, which was only fair, seeing as how Wakefield had graciously granted my request to write a story about him.

The second time I gave Dan Wakefield a ride, it was after a ladies’ book club meeting at the Red Key Tavern. A couple of years after returning to Indianapolis, Wakefield mitigated the inconvenience of not driving by renting a tidy little two-bedroom house with a red door in south Broad Ripple, near College Avenue, one of the city’s few corridors that passes for pedestrian-friendly. Wakefield is reasonably fit, a brisk if slightly stooped walker, and from his home he can hoof it to an upscale grocer, a coffee shop, a few restaurants, and, most important, the Red Key. In 2014, BuzzFeed named it one of the “12 Historic Bars Every Book Nerd Needs to Visit”—in the world—because it was the late Kurt Vonnegut’s “favorite watering hole,” where it wouldn’t have been unusual to see him “writing and drinking in his booth,” and the tavern “also made an appearance in Dan Wakefield’s 1970 novel Going All the Way.”

Book nerds in Indianapolis quickly pointed out that Vonnegut might never even have crossed the Red Key’s threshold, let alone adopted it as his favorite drinking haunt. Sometimes when Wakefield is waxing rhapsodic about the Red Key, he will bring up BuzzFeed and, while careful not to seem ungrateful for the distinction, note that the bar doesn’t even have booths. (Although fairly speaking, Wakefield’s definition of “booths” might be stricter than BuzzFeed’s, as the padded bench and tables that line an entire wall are easily mistaken for them.)

In fact, BuzzFeed’s historical inaccuracy probably resulted from a careless conflation of Wakefield’s Indianapolis legacy with that of Vonnegut, his literary benefactor and longtime friend. If the clickbait website had but substituted Wakefield’s name for Vonnegut’s, its description of the Red Key would’ve been pretty much spot on. The Red Key did indeed make an appearance in Going All the Way, and an encounter Wakefield had there in the ’50s, with his future best friend, gave him the idea for one of the settings in the book. 

Pairing authors with bars is a proud literary tradition, and not only does Wakefield not downplay his association with the Red Key, he revels in it. The Red Key is the closest thing Indianapolis has to the White Horse Tavern in Greenwich Village, where poet Dylan Thomas is said to have downed his last drink before finally succumbing to alcoholism (and where Wakefield himself used to drink), or any of those other bars of lore in more cosmopolitan cities, where the F. Scott Fitzgeralds and Ernest Hemingways supposedly liked to pickle their genius. But unlike at those places, a literary tourist in Indianapolis can drop into the Red Key and actually have a decent shot at spotting the local author-of-legend. Don’t know what Wakefield looks like? He’s the guy in the painted portrait that hangs on the wall above the jukebox.

On the evening I’d agreed to meet Wakefield to observe his appointment with the ladies’ book club, I beat him to the Red Key by several minutes, so I sat at the bar and quietly nursed a bottle of Stroh’s while I waited, feeling guilty that I hadn’t offered to pick him up on my way to the bar.

Right on cue, a guy two stools down said something inaudible about “Wakefield” to the bartender, then asked, “What’s that book Dan wrote about the Red Key?”

Going All the Way,” the bartender answered. “They did a movie, too.” The bartender, Jim Settle, took over the tavern from his dad, Russ, who had a cameo in the film, and he has no doubt endured more than enough Going All the Way small talk. But it can’t be bad for business.

Then Settle, also right on cue, looked up at the front door. “Speak of the devil.” I want to believe that when Wakefield walked in, mere moments after the man at the bar asked about him, it must’ve made that man’s Red Key night. But I missed his reaction because Wakefield, in that stooped but purposeful walk of his, was on a beeline to the back table, and I wanted to greet him before he approached the book club, so I wouldn’t have to walk up by myself to a group of unfamiliar 60-something women, now one drink into the evening, maybe two.

“Dan’s recognized as this sort of literary elder statesman, and everybody loves Going All the Way, but there’s so much more to him,” says his friend Travis DiNicola, “and if people really knew of his background, they’d be kind of blown away, like, Oh, my God, this guy lives amongst us?!”

Wakefield wore his usual getup of V-neck sweater over collared shirt, jeans, and sneakers, except the nice version—the knit dark and tight, the cuffs and collar pressed, the jeans cut fashionably, with black-frame eyeglasses punctuating the outfit’s overall writerly effect. I was there to be a fly on the wall and beyond that wanted as little interaction as possible. But there was no way around it: My unannounced presence had to be accounted for, and Wakefield ceded the floor to me, so I explained who I was. The reaction was kind of a collective ooohhh (paraphrasing here), which I interpreted as excitement over the book club’s getting to welcome not only celebrated author Dan Wakefield, but also a magazine writer tagging along to profile said author—levels on levels—proof, as if more proof were needed, that the famous author gracing their book club was in fact a famous author.

The club consisted mostly of women who grew up and still live on the north side of Indianapolis, not far from where Wakefield is from. For the first 15 minutes, they asked Wakefield if he knew so-and-so, went to high school with what’s-his-name, had ever dated such-and-such’s sister, as strangers in Indiana will do to break the ice. Then the host of the meeting, after giving Wakefield a Ziploc baggie with a slice of pumpkin bread in it, spoke up to introduce the book club formally and explain that they’d devoted an entire year to reading Hoosier authors. After choosing that month’s selection, Going All the Way, she’d carried the book into her doctor’s office to read in the waiting room. When the doctor saw it, he told her Wakefield had also honored an invitation to his wife’s book club. So tonight’s host knew, as she said with a mischievous twinkle, that Wakefield was “book-clubbing around.”

Impish and affable, Wakefield unwound his Going All the Way spiel: not autobiographical, except for the kernel planted in Wakefield’s literary imagination in 1954, when he returned home from Columbia University over Christmas break and, at the suggestion of a teacher, met up with another Shortridge grad named Ted Steeg, who planned to attend Columbia. As the years went by, Wakefield established a career in nonfiction—a successful one—but wanted to write a novel. He tried to envision what two fictional young men might have gotten up to had they spent an entire summer palling around in 1950s Indianapolis, chasing women and fearing they’d be stuck there for the rest of their lives. And in 1970, Going All the Way was born. Steeg was the only real person on whom any character in the novel was based, namely “Gunner,” a Korean War veteran, popular high school jock, and formidable “cocksman.” In the book, Gunner does down beers at the Red Key with “Sonny,” the wry, disaffected protagonist (who is kind of a Midwestern “Holden Caulfield” of The Catcher in the Rye, a book to which Going All the Way is often compared).

But Sonny, as Wakefield explains adamantly and often, and repeated to the book club women, is not a young Wakefield. “No one believes I made the damned thing up.”

True to his depiction in the book as a lady-killer, the book club women seemed more interested in Gunner, anyway.

I’m so glad you made Gunner the character you did. I just loved him. He had such soul.

I’m in a mixed marriage—I’m Jewish and he’s Catholic—so I was really interested in the relationship between Gunner and the Jewish girl.

And so on.

Gunner’s avatar, Ted Steeg, was to Wakefield what counterculture legend Neal Cassady was to Jack Kerouac, Ken Kesey, and Tom Wolfe: a charismatic muse who appeared in books but didn’t write them. (Steeg was, however, a filmmaker, and he spent decades producing the informational movies New Yorkers watched before serving jury duty.) As Wakefield told the book club, after his fateful first meeting with Steeg at the Red Key, the two became fast friends, and Steeg slept on the floor of Wakefield’s basement apartment in New York before they got a place together in Greenwich Village. As Wakefield’s career took him to Boston, L.A., and elsewhere, Steeg married and remained in New York, and Wakefield describes returning there to visit over the years as some of his fondest memories, sitting around in the living room by a crackling fire, listing to jazz records, and ordering out for Chinese. He hasn’t brought himself to return to Greenwich Village since Steeg’s death in 2014, and he told the book club he probably won’t.

As the meeting wore on, the book club talked about how, unlike the female characters in Going All the Way, they had access to the pill when they were young women in the ’60s, and one of them shared that when she was growing up in Northern Indiana, she was taught that Jews and Catholics were “colored.” A television in the bar was tuned to Wheel of Fortune, and Wakefield got harder and harder to hear over the inane bells and bleeps. Out of nowhere, an attractive blonde woman who looked to be in her 50s walked up behind him, reached over his shoulder, and dropped a note in his lap. They had a kind of conspiratorial conversation for about 30 seconds, and she walked away. I made a mental note to ask Wakefield about the mystery woman later, but finally decided not to. That, in the parlance of Going All the Way, was one of the most impressive demonstrations of cocksmanship I’d seen in quite some time, and I was afraid Wakefield’s explanation would reveal the transaction to be perfectly innocent and therefore disappointing.

Finally, after the book club went around the horn taking turns identifying what each liked (and disliked) about Going All the Way, one of the women, perhaps emboldened by familiarity and drink, asked Wakefield if he was presently married.

The query caught the author off guard. “No-oo,” he said suspiciously, the pitch rising between the “N” and the last “o” such that the answer was also a question: What are you getting at?

She pressed on. “Were you?”

“Ye-esss,” he answered, with the same suspicious inflection as before.

“What happened?”

That was enough. “I don’t want to go into all that stuff,” he snapped. “I just write the books.”

The awkward silence that followed felt like a fine time for me to offer Wakefield a ride home, and he accepted. But before we could leave, I took pictures of Wakefield with the group, using one of the women’s smartphones, then all of the women’s smartphones, and then I used each woman’s smartphone to take pictures of each woman individually with Wakefield.

The reason I hadn’t offered Wakefield a lift sooner was that, unlike the first time he rode with me, when I’d borrowed my girlfriend’s respectable if gently used Nissan hatchback, this time I was driving my rusted-out ’88 Toyota pickup. We climbed in, and I apologized for the windows that don’t roll up all the way. He was polite. His first car, he said, was a ’36 Ford that cost $75, and he kept a tank of water in the back because the radiator was always overheating and boiling over. I neglected to tell him that my license plate was expired and secretly prayed we didn’t get pulled over, which might have provided great material for the story but would’ve been embarrassing as hell.

Before we rolled up to his house, I thanked Wakefield for letting me tag along. “No, thank you,” he said. “I’m glad you were there. It was time to go.” And I knew exactly what he meant. The book club crowd was starting to get restless, and I feared for him, trying to imagine him there, facing it alone.

I was Dan Wakefield’s wingman.

A strangers’ book club meeting. What’s in it for Wakefield? The short answer is, a burger and a couple of glasses of red wine. A longer answer is, Wakefield, a single man who lives alone, spent the evening in his favorite bar with a group of younger women who regard him as a celebrity and wanted to talk about how much they liked his book. Which, next to creative satisfaction, is why—trade secret—a writer wants to be a writer.

Indeed, Wakefield gets out a lot, particularly for a man his age. “I drive and own a car, and he does not,” says Indianapolis writer Kara Kavensky. “Subsebquently, I joke that I am his Uber driver. So we go out to dinner, and we go out to events together. He’s my mentor. I’m honored to call him a close friend.” But, she adds, “there is a cost that goes beyond gas,” because Wakefield “is a curmudgeon.”

“He’s not some sweet old man,” says the younger Kavensky. “What is really entertaining to me is when we go out, and people think we’re on a date, which is always funny to me, and flattering to him. But he gets very flustered if someone thinks that he’s my grandfather. He gets offended pretty easily at that.”

“Dan likes meeting new people all the time,” says DiNicola. But, he thinks, Wakefield also has professional considerations for being visible. “Part of why he goes out there a lot is because he needs to sell books, and he needs to promote himself, and he’s very active in doing that.”

Wakefield turned the dining room of his house into an office, where he still keeps a daily work schedule; he writes regularly for a number of local publications and organizations, one of which still owed him $25 until recently (they know who they are), and he’s partway through a book whose subject he won’t disclose. Boxes of new books sent by publishers are scattered about the floor. “Dan told me on a number of occasions that he never expected to live past 50,” says DiNicola, “that he was living the writer’s life in New York in his 20s and 30s, drinking hard and playing hard like all the other writers around him were, and most of those guys died at a pretty early age. Dan never really thought he’d be living to 84. And so here he is, in his 80s, and even though he’s had some great success over the years, maybe didn’t plan for retirement, and so that’s part of why he’s still working. Because he needs to.”

Wakefield has just finished editing a 1,300-page volume of Vonnegut’s complete short stories, set for publication later this year. And he is a dedicated, enthusiastic advocate for Vonnegut’s legacy and, by extension, his own connection to it. In 1970, the year after Delacorte Press published Vonnegut’s Slaughterhouse-Five—an instant classic—Vonnegut reviewed another title from his publisher in Life magazine. “Going All the Way is about what hell it is to be oversexed in Indianapolis, and why so many oversexed people run away from there,” he wrote. “It is also about the narrowness and dimness of many lives out that way.” In the same review, Vonnegut made a prediction. “I guarantee you this: Wakefield himself, having written this book, can never go home again.” 

Vonnegut’s prophecy was at least partially correct. Wakefield faced an onslaught of angry letters and phone calls. Another of the tales in the quiver of stories Wakefield carries to dispense with ad nauseam questions—this one being, How did it feel to be scorned by your hometown?—is the one about the publisher convincing him to make a stop in Indianapolis as part of a publicity tour for Going All the Way shortly after it hit bookshelves. While he was on a flight, the plane made an emergency landing in Pittsburgh. As the passengers stood on the tarmac, word circulated that the airline had a received a bomb threat from a caller who vowed the plane would “never get to Indianapolis.” Wakefield aborted the visit and didn’t return, at least not publicly, for close to two decades.

Nonetheless, Wakefield remains grateful to Vonnegut, who understood not only what it meant to be “oversexed” in Indianapolis but also what it meant to be an underappreciated writer from there, a colleague whose profile and provocative words helped launch Wakefield’s freshman novel to bestselling heights.   

“Kurt is still saving me from smithereens, providing me work in collecting, editing, and writing introductions to his letters, his graduation speeches, and now a book of his complete short stories,” Wakefield wrote recently in his blog, which he named, presumably with a wink, Coming Home: a blog by Kurt Vonnegut’s oldest living friend. 

Here’s an anecdote about Dan Wakefield dating a famous actress.

In 1992, after living in Boston for nearly three decades, Wakefield moved back to the Big Apple because working on New York in the Fifties had made him nostalgic for the city. Published that same year, 1992, the book chronicles the creative and cultural dynamism of the bygone era, from the perspective of a writer who was enmeshed in it, rubbing elbows with some of its greatest luminaries. A 2001 documentary based on the book included interviews with William F. Buckley and Robert Redford.

For Wakefield, New York in the Fifties was a return to nonfiction. A fixture at the Shortridge Daily Echo as a high schooler, Wakefield filed stories for the Indianapolis Star before he even lit out for college. He aspired to be a journalist, and boy, did he ever become one. On assignment with The Nation in the 1950s, he covered the Emmett Till murder trial in Mississippi and traveled to the nascent state of Israel to become the first Western journalist to interview then–foreign minister Golda Myerson (better known today as Prime Minister Golda Meir). In 1968, The Atlantic devoted its March issue to “Supernation at Peace and War,” Wakefield’s examination of social upheaval in the United States, and the magazine’s 1972 article on “the New Journalism” grouped Wakefield with such icons as Tom Wolfe and Norman Mailer.

Wakefield has had three marriages—“none of them lasted longer than a year and a half”—and he describes his third divorce, from a woman he knew from Indianapolis, as the most painful. He doesn’t like talking about it, “because there are friends of hers here,” he says. “It was a romantic idea,” he adds. “It was just wrong.”

Fresh off the divorce and back in New York, Wakefield got a call from his agent, Lynn Nesbit. “Dan, are you doing anything Thursday night?” she asked. “I have a friend, a woman who’s been through a very bad breakup. I’ve been telling her, ‘You’ve got to go out.’ So, I want you to take her out.”

The friend was actor Mia Farrow. The bad breakup was from filmmaker Woody Allen.

Wakefield met Farrow, Nesbit, and Nesbit’s date for dinner, and afterward, as they walked out of the restaurant, Farrow leaned over and whispered in Wakefield’s ear, “Why don’t you give me a call?”

Wakefield called Nesbit the next day and said, “She wants me to call her. What should I do?”

“For God’s sake,” Nesbit answered, “just take her to dinner like you would anyone else.”

So Wakefield picked up Farrow and took her to a little French restaurant in the Village, thinking to himself, trying to drill it into his own head, Don’t mention the name Woody Allen … Don’t mention the name Woody Allen … Don’t mention the name Woody Allen … He managed not to evoke the offending name, they had a nice time, and the two carried on like that for a while, having casual dinners at out-of-the-way restaurants.

Eventually, Wakefield thought, Jesus, I might as well introduce her to some people, so it wasn’t like he was just sneaking out to dinner with her all the time. Who do I know who’s even remotely a famous person?

Wakefield enlisted the most famous friend he could think of to join Farrow and him for dinner. As they sat down, Wakefield said, “Mia, this is Gay Talese.”

“Oh, yes, you wrote that really mean piece about Frank,” said Farrow.

Talese’s 1966 Esquire article “Frank Sinatra Has a Cold” is an undisputed classic, the standard-bearer for magazine personality profiles, partly because it was written, by necessity, without the benefit of any input or cooperation from its main subject—a “write-around,” as it’s known. Farrow was married to Sinatra at the time of the article—she and Sinatra divorced a couple of years later—and Wakefield was so intent on not raising the specter of Farrow’s ugly public split with Woody Allen, it hadn’t dawned on him that introducing her to Talese would resurrect the uncomfortable memory of her previous high-profile breakup.

Oh, shit, thought Wakefield. This is the wrong thing. 

“Yeah, well, you know why it was mean?” Talese said to Farrow. “Because he wouldn’t speak to me.”

The first time I gave Wakefield a ride, we went to dinner at the Aristocrat on College Avenue, one of the places near his neighborhood he likes to walk to.

He regaled me with stories about his days as a journalist, how when he was covering the Emmett Till trial, he got into a squad car with two local sheriff’s deputies in Mississippi, who took him for a long drive and dropped him off out in the sticks. This is where you get out, boy.

We compared notes on Hollywood women we admire—turns out we both have a thing for Jennifer Lawrence—and he recommended I see Assassination Tango, starring a mature Robert Duvall and a “transcendent” younger Argentinian actress named Luciana Pedraza, whom Duvall married after filming the picture. “I thought, Robert Duvall, you smart SOB,” said Wakefield. “There is one scene in that movie all old guys love. When you’re 80, you’re beyond all that shit. But it made me remember what it was like when I was 60.”

We talked about the shooting of Going All the Way, and I confided that I have a crush on actress Rachel Weisz. “I think Ben Affleck had a crush on her, too,” Wakefield said, then recounted a time near the end of the Indianapolis filming, when he saw Weisz playfully rush her costar as Affleck returned from a morning run, and the two fell to the ground together and rolled around laughing.

Wakefield has enjoyed other dalliances with serious celebrity. Director Penny Marshall optioned his 1985 novel Selling Out but didn’t make it because she started shooting Awakenings with Robert De Niro and Robin Williams. Starting Over starred Burt Reynolds, but in Indianapolis, it is the lesser-known of the films adapted from Wakefield books. “Very nice movie,” he says, “but it had nothing to do with the novel.” After Wakefield’s fling with Mia Farrow tapered off, when the production team for the movie version of Going All the Way were considering actors, Wakefield thought of her, and he gave her a call about the film but neglected to mention he had her in mind for the role of the mother to one of the adult characters. He sent her a script. “That did not go over well,” says Wakefield. “I was later told by several people that was really a dumb move.” It was the last time he had any contact with her.

“You’ve been married and divorced,”  Wakefield’s best friend once told him. “But you never really gave a shit about anybody. And now you do.”

Befitting Wakefield’s profile, advance tickets for a Wakefield event last summer at the Red Key, Uncle Dan’s Story Hour, sold out within a couple of hours of going on sale, and a wait list for tickets to a second edition of the series quickly filled up as well. Wakefield got the idea for the program after a Going All the Way bus tour a few years ago, on which he narrated stops at Indianapolis locations that appeared in or inspired passages in the book. The last and most important stop was the Red Key. Demand quickly exceeded the number of seats on the bus.

A week after the ladies’ book club meeting at the Red Key, Wakefield had a Tuesday-evening appearance scheduled at the Nora library branch on the far-north side of Indianapolis, to discuss his 1982 novel Under the Apple Tree, which chronicles the participation of a 12-year-old Illinois boy in the civilian war effort on the American home front during World War II. Inspired by the author’s own childhood experience, Under the Apple Tree is thematically more serious than Going All the Way, though still humorous in typical Wakefield fashion.

His agreement to participate in the library event was contingent on the library people arranging a ride to get him there. But with just a few hours to go before the talk was scheduled, Wakefield didn’t know if he’d make it, because he hadn’t received confirmation that someone would in fact be picking him up. At the last minute, he managed to get a lift from a Red Key regular.

A New York Times review praised Under the Apple Tree’s “vigor and verisimilitude” and called it an “engaging period study.” The strength of the book, along with the literary notoriety of Wakefield—the guy had a dinner date with Mia Farrow and Gay Talese and talked Frank Sinatra with them, for Chrissake—not to mention Wakefield’s popularity in Indianapolis, might have predicted a healthy turnout for the library engagement.

When he showed up, only three people were waiting: two of the branch’s librarians, and I. 

This past fall, the Kurt Vonnegut Memorial Library booked Wakefield for a reading, and only seven or eight people showed up. The disappointing attendance at Wakefield’s library engagements, in contrast to the Red Key events, might owe to any number of factors—lack of promotion, the general public’s lack of intellectual curiosity, or simply lack of booze. Or maybe Indianapolis just has a limited appetite for Dan Wakefield when the topic isn’t Going All the Way, and the venue is not the Red Key Tavern.

The last time I gave Wakefield a ride, we sat together in his living room for a while first, before, of course, popping over to the Red Key for a drink.

He volunteered an explanation for why he stopped driving in the first place. Not long after he moved to South Beach, a mother and a grandmother approached him at an author event in a Miami bookshop. The grandmother, an immigrant who arrived in the United States fromCuba with the Mariel boatlift of 1980, was writing a novel. She wanted to know, would Wakefield read it and help her get it published. They invited Wakefield to their home for Sunday dinner to talk about the project. Oh, God, this is going to be trouble, he thought. He was reluctant to get involved—if established writers honored all the requests they get from novice authors, they’d never get any writing done themselves. Nevertheless,Wakefield accepted the invitation.

Turned out the novel was in Spanish, so Wakefield was off the hook. But having Sunday dinner in the women’s home, a feast of pork and rice and fried plantains, became a tradition. Wakefield learned that the mother was divorced with two young children, a 5-year-old girl named Karina and her younger brother, Kalel, who was severely disabled. “All the attention in the house was on him,” Wakefield told me, “and the grandmother, ‘Abuela,’ devoted her whole life to taking care of him, 24 hours a day. And so nobody was paying attention to Karina.”

Wakefield never had children, and, truth be told, he never really wanted them. He’d been around friends’ kids and, by his own admission, never “got it.” But there was something about this girl who, though surrounded by people who adored her, was really kind of alone—much like Wakefield himself.

One day after dinner, he asked Abuela if he could take Karina for a walk, and Wakefield’s “walk around the block” with Karina became part of the Sunday-dinner routine. He started taking her to Sunday school at a church in Coral Gables, where they befriended another man and his daughter, and “he loved to drive, thank God,” so the other father took the four of them on field trips all over Miami—butterfly exhibits, Sea World, the movies. Wakefield got to know Karina’s teachers, helped with her homework.

An aging white author from white-bread Indiana, benefactor to the daughter of a noisy Cuban-refugee household in Miami. The mother and grandmother honored him with the title of godfather, and they became the family he never thought he wanted.

“I remember calling Ted Steeg once,” Wakefield told me as we sat together in his living room. “Ted had a daughter that he had basically raised, and I would always ask his advice about things. And I remember telling him once about this great day I had had with Karina.”

Steeg listened as his old friend described the unlikely relationship with the Cuban family. “Wakefield,” he said, “I think you’re in love for the first time.”

“What are you talking about?” Wakefield replied.

“You’ve been married and divorced,” said Steeg. “But you never really gave a shit about anybody. And now you do.”

For the first time, Wakefield knew what it felt like to be a father.

When Wakefield was a boy, an eccentric aunt named Ollie—who lived in a cabin in the woods, played the organ, wrote poetry, and, in her younger days, held séances—took his hand, closed her eyes, and said, “You will be close to death, and you will recover.” Years later, during a break from college, he was in a terrible car crash that left him with a broken neck and subjected him to three months in traction and three more months wearing a body cast. Still, he took up driving again.

“The moment I stopped driving was—my goddaughter in Miami is one of the most important people in my life, and I used to drive her around all the time, and her friends,” he told me. One time, Karina and her cousin needed a ride, so Wakefield agreed to pick them up. The gas station where he met them was in an unfamiliar part of Miami, and Wakefield—who, as people close to him will attest, can be prone to excitability—was nervous. After the girls got into his car, he accidentally stepped on the gas pedal and the brake at the same time, and the car shot forward, into a concrete wall. “I very quickly put it in reverse, and I got back off the wall,” Wakefield recalled. “But I just said, That’s it, because if I had hurt her, if I had done anything to put her in—that would have killed me. I said, That’s enough.” He hasn’t driven since.

Wakefield had initially told me about Karina the first time I gave him a ride, a couple of weeks earlier. On that occasion, after dinner, he invited me into his house and showed me the happy, framed photos of Karina that line a shelf under a window in his office. How Wakefield ended up back in Indianapolis—and in so doing left Karina behind in Miami—is by now pretty well known; it’s a story he’s told many times. But why is a question to which getting a satisfying answer from Wakefield is more difficult. He has one of those pat responses—that he’s always decided to move based on intuition, instinct.

That reliance on an inner voice might owe to Wakefield’s faith. After becoming what he describes as a “Hemingway atheist” in college, he rediscovered religion while living in Boston, which led to a kind of a third act in his career: a memoir called Returning: A Spiritual Journey, regarded by many as an exemplar of good writing about religion, and it spawned several follow-up books and a busy itinerary of traveling the country to teach seminars on spiritual autobiography.

So, when it is time for Wakefield to move, he just—knows. And each move has rewarded him with “wonderful, total coincidences,” as though he were meant to be in each place he’s landed.

Like how, when Wakefield was still working at Florida International, he invested in a college fund for Karina, and after she graduated from high school, he helped her get into Harrison College in Indianapolis so she could train to be a veterinary technician. She needed a part-time job while she was in school, and one day while Wakefield was walking down Broad Ripple Avenue, he saw a cardboard sign in the window of the Taste of Havana restaurant. HELP WANTED. He called Karina, she dropped in for an interview, they hired her on the spot, and, for the year she lived in Indianapolis, the owners, who hailed from Cuba, became like a second family to her.

But Wakefield is like family family. “My grandmother would always describe our bond as if we knew each other from another lifetime, and that is really how it feels,” says Karina. “The thought of losing him, and him being old, is such a heartbreaking thought to me. I never want him to not be here anymore.”

Karina, the one person Wakefield ever truly gave a shit about, at least in his best friend Ted Steeg’s estimation, is back in Miami now. Steeg died two years ago. Wakefield has reconnected with a group of close friends from Shortridge High School, and they all get together regularly for dinner. The group has grown smaller since they started meeting a few years ago. That last time I gave Wakefield a ride, he had attended a memorial service for his friend Evans Woollen earlier in the day. “The tough thing about this stage of life is losing friends,” he said.

“I don’t see picking up and moving someplace else,” he continued. “But I don’t know. I’ve never known. I could never foresee it. So I have no idea what’s—” His voice trailed off before he could finish the thought. Because let’s face it, no one really knows where, or when, the ride will end.

But if Wakefield is, in fact, still working because he needs to, as his friend DiNicola surmises, another kind of need might help explain why the author returned to Indianapolis, and why he might stay here, even if he himself is unwilling or unable to put it into words.

During the time when Wakefield was going out with Mia Farrow, a friend of his called and wanted to know if he’d seen that morning’s New York Post Page Six. Wakefield stepped out, picked up a copy, and read something like, “Last night, Mia Farrow was seen at the such-and-such restaurant in Greenwich Village with an unidentified companion.”

Wakefield was amused by the slight, and he still jokes about it. “I figured that could be the title of my last memoir, Unidentified Companion,” he says. But the incident might be emblematic of a larger truth about Wakefield’s career.

“I think Dan’s whole body of work is really under-recognized, actually,” says DiNicola. “Yes, Dan’s recognized as this sort of literary elder statesman, and everybody loves Going All the Way, but there’s so much more to him, and if people really knew of his background, and his work as a reporter, as a nonfiction writer, his other fiction, his work in TV— they’d be kind of blown away, like, Oh, my God, this guy lives amongst us?!

About two years ago, DiNicola arranged a private dinner for Wakefield and author John Green, whose bestselling book (and hit film adaptation) The Fault in Our Stars made him the “it” writer of Indianapolis. At one point during the dinner, DiNicola excused himself from the table, and their waitress stopped him as he walked to the restroom. “Do you know who you’re sitting with?!” she said. “Oh, my God … Oh, my God … Oh, my God.” The waitress started yammering about what a big fan she was, and DiNicola assumed she was starstruck by Green. When DiNicola returned to the table, the waitress, beside herself, brought over a menu to have it autographed. “And John sort of perks up, like to grab his pen or something,” says DiNicola. “But she went to Dan first and started gushing about what a fan she was of Dan’s work.”

More than anyplace else, Indianapolis, which loves to cheer local boys made good, is where Wakefield is likeliest to find that kind of love.

I told Wakefield that I intended to write about people driving him around. He winced a little and shifted in his chair, and it suddenly occurred to me how that probably sounded. I would make him look like some kind of freeloader, a burden, helpless.

He narrowed his eyes, and the kindly grandpa face turned accusatory. “Who are these people who supposedly drive me around?” he asked. I named DiNicola, Kavensky, and a couple of others, and Wakefield conceded that, yes, he rides with those people, usually when they’re going someplace together, anyway. But he does have a paid driver: his cousin Justin, whom Wakefield employs to take him to appointments and such. And Wakefield insisted I acknowledge a woman named Donna Foster, who attended one of his writing workshops with her husband, Gerry, and when Wakefield mentioned that he had a dentist appointment the next morning, the couple raised their hands, said they were retired, and volunteered to give him a lift.

I tried to explain myself to Wakefield, and believed it, that giving him a ride probably feels more like a favor to the drivers than to him. They get one-on-one time with a twice-bestselling author who met Golda Meir and dated Mia Farrow.

And all Wakefield gets out of the deal is a ride.