Searching for Heather Dean

In a new memoir, a former entertainment journalist shares why she gave up a glamorous career to pursue newfound dreams in Israel

A poised, statuesque woman enters the main hall of the OU Israel Center in Jerusalem. She is about to launch her memoir, Searching for Heather Dean: My Extraordinary Career as a Celebrity Interviewer and Why I Left It. The audience waits, rapt with curiosity, as she peruses her notes before she begins speaking.

Today, Heather Dean produces a popular weekly podcast for Aish.com. Courtesy of Heather Dean

A highly successful celebrity interviewer, Heather Dean has conducted more than 1,500 interviews with the likes of Robert Redford, Brad Pitt, Isabella Rossellini, Harrison Ford, Reese Witherspoon and Martin Scorsese. (And for this article, she gave a personal interview to Jewish Action!) But the most inspirational stories in her book are her own, written with sparkling wit and emotion—and no sugarcoating. Her bottom-line message: “Remember who you are.” For Dean, it took about thirty-five years to discover exactly who she is.

Born and raised in the affluent Cleveland suburb of Shaker Heights, Dean had a fascination with TV. This obsession, along with not belonging to any particular clique, certainly not the “cool kids,” led her to spend hours watching, analyzing and dreaming of working in the entertainment industry.

“I used my tenure as a teenage social outcast to hone my skills as a perceptive observer of people,” said Dean, who shared that she would often be invited to braid the hair of other girls, but not invited to their parties. Her experiences also helped her to be empathetic later in life to young people who consider themselves outsiders.

Growing up, Dean attended Hebrew school, which left her uninspired. Moreover, she found the Conservative synagogue services “maddeningly and mind-numbingly endless.” She felt that being shown films about Judaism on Shabbat, being driven to synagogue and being allowed to write and cook on synagogue premises on Shabbat was a classic case of “Do as I say, not as I do.”  “It certainly didn’t have a positive effect on me,” she says.

A Rising Career
One summer, while visiting her parents who had moved to Portola Valley, California, Dean was accepted as an intern at People Are Talking, San Francisco’s highest-rated morning TV talk show at the time, which was broadcast on KPIX, the Bay Area’s CBS affiliate. She loved being part of the team and getting her foot in the door. She saw many women in senior- and executive-level production positions who were making important decisions. People Are Talking Producer DeAnne Hamilton gave her the following advice: “Go for it. Just go for it.” The lesson in courage served her well.

“That life-altering summer [internship] was ultimately bittersweet. I could foresee a future in broadcasting that looked promising. It was also the summer my mother learned she had cancer,” she writes in her book.

“She broke the news to all of her children in the most nonchalant of ways . . . I didn’t want to pry details out of her if she wasn’t ready to tell us more. In any case, I preferred the cold comfort of denial to the hard truth that she might leave this world in the near future.”

Dean returned to Case Western Reserve University in Cleveland, and convinced the school to let her spend her last semester as an intern; subsequently, she was accepted by MTV in Manhattan as one of three news department interns, marking the fulfillment of a dream. She moved up the totem pole, eventually becoming a premier entertainment journalist working for E! Entertainment Television, the Associated Press News Radio and other television networks.

Dean has positive things to say about some of the celebrities she interviewed, even as she grew, over time, to reject their lifestyles and choices. Thus we learn that neither George Harrison nor Sinéad O’Connor displayed “an ounce of arrogance”; Rosie O’Donnell “avoided speaking unkindly about other people”; and Robin Williams was “totally open with you . . . Throw him a topic, and he’d weave a hilarious tapestry.”

She joined a press junket to Houston for the release of the Hollywood drama Apollo 13, met with the leads and director, declared Tom Hanks “a mensch” and quoted him as saying, “About every five years, I’ve gone through some sort of process of reexamining where I was in life, as a man, as an actor . . .”

Nevertheless, the more Dean spoke to actors, the more she witnessed their constant battle to stay young, relevant and successful. “I have been told by such stars as Madonna, Gary Oldman and Drew Carey that fame and popularity do not solve your problems, nor do they wipe out your inner insecurities and struggles.”

Beginning a Journey
Dean had always been a rather spiritual person, but the heartbreaking diagnosis of her mother’s cancer, as well as her own struggle with health issues, was a turning point.

She writes in her book, “I couldn’t change my mother’s situation, nor heal her, but this ‘detour’ and concern about health was the necessary catalyst for me to make some major lifestyle changes of my own.”

After her mother’s death in 1995 following a long illness, Dean fell into “an emotional fog” and sought counsel from a rabbi. A friend gave her a list of four local rabbis on Manhattan’s Upper West Side, where Dean lived at the time. She called the first one on the list, Rabbi Avraham Goldhar, who, along with his wife Yocheved, became mentors who shepherded Dean on her spiritual journey.

One day—amid a life busy with movie screenings, Broadway shows, comedy gigs and dress rehearsals of Saturday Night Live—Dean realized that she had no one to interview. It was Rosh Hashanah, and all of the celebrities’ publicists “were in Temple!”

Fame and popularity do not solve your problems, nor do they wipe out your inner insecurities and struggles.

Dean went home, dressed modestly, and walked to Aish HaTorah New York, where she had previously met with Rabbi Goldhar (wondering all the while what the word “Aish” on the building meant). “So I won’t enjoy myself,” she recalled thinking, “but I’ll kill some time.” Amazingly, she discovered that, although she had not read or spoken Hebrew in twenty years, she was able to follow the service—something she attributed to “an act of God”—and she even recognized some of the melodies. “Despite myself, I found myself fighting back a tear.”

She began to attend classes at Aish, although she was sure she would not go as far as observing Shabbat, keeping kosher or regularly attending synagogue. She thought of herself as pro-God and anti-religion. “I was already on a spiritual path that was a philosophical path, but not adhering to any rules. The only rituals I adhered to were taking a shower every morning after a race walk in Central Park and then getting dressed while listening to The Howard Stern Show.”

So another Yom Kippur came and went, and she didn’t fast. “I perceived myself to be a ‘good person’ who didn’t require atonement. I knew I wasn’t perfect, but I figured I was also far from being a sinner.”

But Dean continued to question and investigate. “I consulted with [a religious woman] who used to be a staunch feminist, about male-female relationships, wondering, for instance, how realistic being shomer negiah is in this day and age. The next hurdle was handling twenty-five hours of Shabbat.”

Dean writes about falling for a non-Jewish man and walking away from the relationship, even though, at that point, she was not yet fully Torah-observant. During a pivotal conversation with Rabbi Goldhar, he described some of the potential conflicts that could arise over religious issues, asking Dean, “What long-term goals do you share?”

Writes Dean: “[It was a] simple question, but it had me stumped. Who could think of long-term goals when the present was so all-encompassing and delightful?”

Subsequently, Dean met her then-boyfriend at a Starbucks, but “he didn’t take the bait” when she told him that she “could only be in a relationship with a man who was either Jewish or interested in learning about Judaism.” He smiled and stayed silent. Then the tears came. She writes, “It was the hardest goodbye to a man I had ever said.”

Although Dean had been to Israel a number of times as a young girl, as she attended more and more classes at Aish, she decided to join a few of Aish’s trips to Israel. It was during a trip in 1999 that she knew she was ready to make some dramatic changes.

She writes: “Nothing prepared me for the exquisiteness and majesty I would feel from seeing the Golan Heights with my eyes and . . . my soul.”

Dean’s memoir Searching for Heather Dean: My Extraordinary Career as a Celebrity Interviewer and Why I Left It, which she presented at a book launch at the OU Israel Center in September.

“We were going north along the road bordering Jordan . . . and the further we went north the more it impacted me,” she said. “I was already praying from a siddur, and the Morning Prayers [talk] about the goodly land; . . .  it was connecting the prayer book to the land. That’s spirituality—seeing the actual land and knowing that Hashem made good on His promise.”

Back in the States, New Year’s Eve 1999 arrived on a Friday night, and Dean had “an invite to almost every party in town.” But instead of spending it at “the party of the century,” Dean, who had started attending Shabbat services regularly, made a fateful decision: She spent New Year’s Eve at Aish, enjoying a lovely Shabbat meal and dancing with women singing Yibaneh haMikdash. “That’s how I brought in the new millennium. I decided to celebrate a new era in a way that joined me with my fellow Jews, my spirituality and my identity.” She searched inside herself and finally declared, “I could be so much more.” It was a seismic shift for her. And regarding God, she writes: “He waited until I made this decision—with a full heart.”

Eventually, Dean decided to study Torah at Neve Yerushalayim in Israel. “I was happiest when I was in a Torah class.” Yet, she still felt that she had a foot in two worlds. “It would take me many years to figure out how to meld the best of both of my lives.”

While living in Jerusalem, Dean found a role model in Rebbetzin Chaya Levine, a woman steeped in chesed while balancing family and work responsibilities. And as Dean met more and more people like the rebbetzin on her new journey, the more she felt they engendered more meaningful experiences than she’d ever had interviewing celebrities. (Years later, Rebbetzin Levine became an even greater role model to Dean, exemplifying great faith and nobility when her husband, Rabbi Kalman Levine, was murdered in the terrorist attack at a synagogue in Har Nof in 2014.)

A New Chapter
When she felt ready, Dean joined the shidduch scene in Israel, and was introduced to Andy Haas. The two hit it off, and got engaged in Israel, where they planned to live. And then, on December 1, 2001, on a Saturday night, they were thirty seconds away from a bombing attack on Ben Yehuda Street in downtown Jerusalem. Eleven teenagers were killed by two suicide bombers that night. She said to Andy the next day (when he told her how close they had been). “Since [God] spared us from getting so much as a scratch, I think we should repay Him by having an exceptional marriage . . . we should give back to the community and show God that we deserved to be spared—that we’re using this gift of life to be solid members of His team.”

Dean felt her mother’s presence at their wedding, held in New York a few weeks later, and felt like all of the numerous phases of her life were coming together “in a glorious crescendo.”

“Part of accepting a life of Torah and faith in God means knowing that both our gifts and our challenges are given to us for a reason,” Dean writes in her book. “Nothing God does is random, arbitrary or without purpose.”

Dean presenting a workshop on the “Power of Podcasting: Promoting Your Published Work with Successful Podcast Interviews” at the Jerusalem Women’s Writers Seminar in 2018. Photo: Reuven Ansh Photography

Reflecting back on her career while at the book launch, Dean says, “It really was a lot of fun and an extraordinary career. But here we are in Jerusalem, and [it’s] a more meaningful life than anything outside the Land of Israel and outside of Torah Judaism can provide.”

Dean and her husband were blessed with several children, all of whom were born when Dean was already in her forties. She spent a few years as a full-time mom—enjoying every minute it.

Once her children became school age, Dean decided to return to broadcast journalism, using her talents and skills to spread Torah. She hosted Israel News Talk Radio’s Conversations with Heroes and The Modern Jewish Home. Presently, she produces a popular weekly podcast for Aish.com called At Home in Jerusalem, where she interviews Torah personalities on Judaism, family life and other issues.

She quotes Rabbi Noah Weinberg, zt”l, on the question: What is real happiness? “Happiness is appreciating what you have—counting your blessings.”

She concludes her book by recalling a sentiment from Pirkei Avot 4:1: “A rich person is a person who enjoys what he has . . . I’m aiming for that.”

Toby Klein Greenwald, a regular contributor to Jewish Action, is a journalist, playwright, poet, teacher and the artistic director of a number of theater companies. She is the recent recipient of the Lifetime Achievement Award from Atara-The Association for Torah and the Arts for her “dedication and contributions in creative education, journalism, theatre and the performing arts worldwide.”

Sidebar: Exclusive Interview with Heather Dean

JA: What was the most moving or exciting interview you did from your old life and from your new life? 

HD: From my old life, it was the first time I interviewed Mike Wallace of 60 Minutes. Knowing his reputation and the fear he strikes into people . . . but within one minute I could tell, this man is a pussycat, and he gave the most professional interviews because his sound bites were clear and concise.

In my new life, I would say Rabbi Berel Wein, because, in the religious Jewish world, he is admired by people from all streams, and through his TV show Ask the Rabbi he reaches a broad spectrum of Jews. He has a depth of scholarship in history and the Bible, and is a giant in our times. He’s also very humble.

JA: What advice do you have for a would-be journalist/interviewer?

HD: Know the body of work of the person you’re interviewing—or at least read or watch whatever they are promoting. Be nonjudgmental in your everyday life, and your interviewees will pick up on that vibe and speak more freely.

JA: What would you say to someone who is thinking of going into broadcasting or the performing arts?

HD: It’s tough, because you will be expected to work on Saturdays. Going into that field in the frum world? I’d say, welcome to the club, and know there is already a [creative] community that will help you grow professionally.

JA: How does one retain humility in that world, even in the frum world?

HD: Have kids! . . . When you’ve had that kind of a day that your career gets a [positive] bump, you have to remember you’re an eved [servant of] Hashem. Remember who you really are.

JA: If you could meet any of these celebrities again, what would you ask them today?

HD: I would ask Oprah about spirituality, not because she’s so famous, but because she’s so influential. [When I interviewed her] she was a joy, stayed on topic, had a rich vocabulary. . . . I’d ask her about her spiritual journey. She has overcome a great deal of adversity.

JA: What guidance do you have for those who become Torah-observant, regarding family relationships with those who are not?

HD: To be very accepting. . . . Don’t have high hopes that you’ll change any minds. Rather, hope that they will accept you on your journey.

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This article was featured in the Winter 2019 issue of Jewish Action.
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