Katie Couric is as used to making headlines as she is to reporting them. Media coverage of her departure from the Today show to become the first female solo anchor of a primetime news program (CBS Evening News with Katie Couric) and last year’s venture into TV talk-show land (with Katie) rivaled that of a presidential contender on the stump. Rumors are swirling again—about the show’s cancelation, and Couric possibly replacing Barbara Walters on The View. But nothing seems to faze her. As she well knows, where there’s uncertainty, there’s also opportunity.

Not long ago, Couric had dinner with her pal of many years, Sheryl Crow (who created the theme song for Couric’s talk show) at the Gotham Hotel. Like Couric, Crow is an ardent cancer activist and supporter of Stand Up to Cancer, an organization Couric cofounded in 2008.

The wide-ranging conversation ranged from the personal—dating woes of super successful Manhattan women and who Couric turns to when making big career moves—to the city post-Bloomberg, the reasons she changed the focus of her cancer advocacy, and why you never want her to cook Thanksgiving dinner.

Sheryl Crow: Let’s talk about your engagement. You’d been dating John [Molner] for a year and a half, but was it still a surprise to you?
Katie Couric: We had been talking casually about the possibility of getting married. We knew we were in a committed relationship, but we had not really discussed it in concrete terms. When John said he was open to it, I thought, Great, but I also didn’t want to push it in that direction if that wasn’t where he was headed.

SC: You wanted to get remarried?
My preference was always to get remarried, but I was also open to being in a Goldie Hawn/ Kurt Russell situation. I have a lot of respect for the institution of marriage; it was very old-fashioned that John proposed. I had absolutely no idea. In a world where we plan everything and you want to be in control of everything, it’s nice for someone else to take control.

SC: This is a totally superficial question, but I have to say that I think your fiancé did a very good job with the ring.
Want to hear a really weird story about the ring? This is a Gotham exclusive….
SC: Woah! Breaking only in Gotham!
KC: John had been looking for a ring, and he ended up at a store called Stephen Russell. They showed him a dozen rings; he picked one right away and said that’s Katie’s ring. What he didn’t know was that a number of years ago I had said to Stephen, “If I ever remarry, make sure whoever comes here gets me that ring.” It was the ring John picked out!

SC: You’re a super successful woman, and successful women in Manhattan say it’s tough to find a good partner. Any advice?
Finding the right partner takes almost as much focus and commitment as a career. If you want to be married, I think it’s a numbers game. You have to cycle through the system. I basically asked people who I thought had similar values to me to please introduce me to somebody.

SC: As accomplished women—and I am guilty—you have to make room for [a partner]. One of the great things about you is that you are always open. I don’t think that all women who are super successful—and it’s true of men, too—allow themselves to be open.
People put up so many walls and are so afraid of getting hurt. I’ve been hurt, too; I’ve had to deal with a lot of sadness and some failed relationships. But you’re never going to get anywhere unless you’re receptive to people. I’m so glad I was because look what I found.

SC: Speaking of successful women, what are your thoughts on Sheryl Sandberg’s Lean In, which makes the argument that women can indeed have it all, and Anne-Marie Slaughter’s essay in The Atlantic saying they can’t?
I sometimes worry about this one-size-fits-all philosophy because everyone’s life takes different twists and turns. I agree that in order to get more women in the upper echelons of corporate America, government, or media, it’s important they focus on their careers in their 20s. The higher up you are, the more indispensable you become and the more flexibility you’ll be given. But I also think that everyone forges their own path, and that doesn’t mean you can’t have children and also be very successful. There are so many different roads to get to where you want to be. Every day is a winding road, Sheryl....

SC: If it makes you happy....
It’s hard because women shoulder the child bearing and rearing. It’s getting better and becoming more of a partnership, but I still have male friends who say they’re babysitting their kids, and I’m like “That’s not babysitting…. that’s parenting.” They shouldn’t expect an award or applause because they’re taking care of their kids.

SC: You’ve made bold choices in your career—first solo female anchor on the evening news; then you started your talk show. Tell us about your decision process when making a big career move.
I love a challenge, I like to get out of my comfort zone, and sometimes I leap before I look because I think you have to try to set yourself up for success as much as you can.

SC: Who have been your sounding boards?
My newest sounding board is John Molner. My father, who was a former journalist, used to be so helpful. I turn to people like Andy Lack, who I worked with at NBC, and Howard Schultz, the CEO of Starbucks. I appreciate the perspective of people who are in different businesses, who I think are quite visionary. I have a variety of sounding boards, but for the most part I try to listen to what my gut is telling me because I think I’ve had pretty good instincts throughout the years.

SC: The best career advice you ever received?
A friend of mine on the Today show said, “A ship is always safe in the harbor, but that’s not what ships are built for.” That’s a really nice metaphor for taking risks and trying new things.

SC: What’s your proudest achievement career wise?
I think helping to bring the Today show to number one and keeping it there. I was very involved with it behind the scenes. I wanted it to have intelligence and a sense of fun. I think helping to drive that ship as long as I did... I’m really proud of that.

SC: With career success, how much is it hard work, how much is it luck?
I think Thomas Jefferson said, “The harder I work, the luckier I get.” I have been at the right place at the right time, [but] if I didn’t have the work ethic to back it up, it would have been a short-lived thing.

SC: You’ve met everyone from the Queen to the past four or five presidents. Who really wowed you, and why?
Tony Blair—I just thought he was incredibly eloquent even though I know he’s exceedingly unpopular now. Also, Hillary Clinton, General Norman Schwarzkopf, General Raymond Odierno, and Paula Coughlin of the Tailhook scandal.

SC: What’s your most unforgettable work experience?
9/11 because I watched it unfold and had to report on it in real time. I was in a state of shock like everyone else in the world.

SC: Your toughest interviews?
Ross Perot was very belligerent and dressed me down. David Duke was tough because I was tough on him. Harrison Ford is not particularly loquacious, which has its pluses, just not when you’re doing an interview.

SC: Who is the ultimate get for you, and why?
Kate Middleton because she’s so enigmatic; the Pope because he’s been surprisingly forward thinking and outspoken; and I would love to interview Harper Lee.

SC: You’ve been very active in fundraising for colon cancer. Tell us about that.
When my husband died, I thought I had a built-in bully pulpit to educate people about the second leading cancer killer of men and women [in the United States]. To demystify the procedure, I had a colonoscopy on television and to this day people say to me, “I was screened because of you.” Some people even say it saved their lives. We’ve helped support colon cancer research and awareness efforts, but then I transitioned into being one of the founders of Stand Up to Cancer. I felt all cancers deserved attention and all cancer research needed funding, so I wanted to expand my efforts. I feel so proud of the work Stand Up to Cancer has done. We’ve been able to support dream teams and for the first time scientists are collaborating and not competing. As a result they are really making progress and coming up with innovative ways to attack this disease.

SC: Do you support other charitable causes?
I believe education is a great equalizer, and unfortunately it’s so unequal in our country. I’m on the board of the Harlem Village Academies, wonderful charter schools in Harlem. I’m also very active in Room To Read, which builds libraries at schools in developing countries.

SC: Thoughts on the city post-Bloomberg?
The next mayor needs to recognize that this is a huge melting pot of ethnicities and socioeconomic levels and create opportunities for everyone.

SC: How do you spend downtime in the city? Are you often recognized?
People in New York don’t really care who you are. I like Central Park. And to go to Broadway shows.

SC: How do you celebrate Thanksgiving? Do you cook at all?
Last time I cooked a turkey, I forgot to take the package with the gizzards out of the cavity. My sister usually makes the turkey, and I go to Boston. There are a lot of grandkids now, and my nieces and nephews and my mom. I bring the pie.

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