Ali Wentworth is simply hilarious—and on many levels. She does it all—TV shows, movies, books, and collaborations with Oprah. From her memorable role as Jerry Seinfeld’s girlfriend “Schmoopie” in the infamous Soup Nazi episode, to her movie roles in It’s Complicated and Jerry Maguire, the actress and comedian always makes you laugh—and best of all, you’re always laughing with her. On top of that, she is also a best-selling author, the wife of George Stephanopoulos and the mother of two girls. Holly Parmelee chatted with Wentworth in her New York City apartment about her tried and true life rules, her “needy” family, and her latest book, Go Ask Ali.

Ali
J.Crew pajamas, Ali’s own; Oscar de la Renta beaded earrings, $450, Neiman Marcus, The Westchester, White Plains, NY

FIND YOUR PASSION
I always knew I wanted to be a performer. I was the middle child of divorced parents and I got attention by performing. I realized I loved comedy when I was doing a serious play in college and there was a scene where I did something improv that got a huge laugh. Once you get a laugh, that’s it, you’re in. All I wanted to do was get more laughs.

STICK TO YOUR GUNS
My parents were not happy with my career choice. They pretended it was a phase—like sleeping with girls in college. They thought I would come to my senses. My mother begged me to also take a typing course in case acting didn’t work out. Even when I started to get real work they still hoped I would quit show biz. Eventually I told my mom how much money I was making—which was three times her salary—and then she had to shut up.

BLOCK OUT NEGATIVE CAREER ADVICE
I heard a lot of “You can’t, you can’t, you can’t,” so I focused on proving them wrong. I heard a lot of “Only 1 percent of actors work or comedy is the hardest thing.” I was always pushing against that.

BE FLEXIBLE ABOUT WHERE LIFE TAKES YOU
My husband and I had a quick romance before we got married. He proposed after two months. His job was in Washington DC and suddenly I was right back where I had grown up. I had two battling feelings. One was like The Godfather: “Just when you think you’re out they pull you back in.” On the flip-side, I was so in love with my husband that I thought, “If this is what we have to do, then this is what we have to do.”  The problem with acting is it’s usually in LA or on location. Family comes first for me and I was never going to work in LA while my husband and children were in NYC. When George became a host of Good Morning America and we moved to New York City I realized I had to find a career that could work around him and the kids. Writing books and creating my TV show, Nightcap, made the most sense.

PUSH YOUR BOUNDARIES
I was contacted by a publisher to write my first book because they had heard me on a TV interview and thought I was funny. I wasn’t sure I could do it, but I like to challenge myself. My books are just stories I tell at dinner parties that I’ve crafted over the years. When you’re a performer you naturally entertain. I knew which stories worked and which ones needed embellishment, so it was not that difficult to write them down in book form. My new book—Go Ask Ali—is advice based on my mistakes in life.

CARVE OUT TIME TO FOCUS
For me to write, the house has to be vacant because I have a very needy family. I have a ritual of cleaning my office, then watching Kelly and Ryan, then having another cup of tea. I’ll then decide to make banana bread. I’m a horribly undisciplined person. I might get an hour’s worth of writing in. To really focus, I’ve occasionally gone away alone for a few days and been able to get a lot of work done.

WORK WITH OPRAH—IF YOU CAN
I was on Oprah for three years. It was a magical place with happy women, delicious food, and presents all the time. I would fly to Chicago on Thursday afternoon, check into a hotel suite, and order room service. No one was trying to have sex with me or pee on me or needed milk. I would do the show in the morning and fly home that afternoon. It was the perfect job because just when I was looking for something more I got this and it kept me engaged in the work world. I did everything from interviewing Lady Gaga, to jumping out of a plane, to going nude on a public beach—which was not the easiest thing I’ve ever done. I mean, 16 years into my marriage and I still turn off the lights off before getting into bed with my husband!

Ali Wentworth
Marc Cain jacket, $530, Marc Cain, The Westchester, White Plains, NY; Theory white cami, $225, The Row cuffed white pant, $1,220, and Siena Starburst necklace, $650, all from Neiman Marcus, The Westchester, White Plains, NY; BB lilac suede pump, $625, Manolo Blahnik, NY

SUPPORT YOUR KIDS’ DREAMS—UNLESS IT’S POLE DANCING
My daughters have both been in school plays and they are so bad that I am happy to say they will not be actors. If I’ve learned anything from how my parents reacted to my career choice it’s to support them. Unless it’s pole dancing I think they should pursue whatever they’re passionate about.

FIND YOUR SQUAD
I like women that have your back, support you and show up. Brooke Shields did a guest spot on my former show, Nightcap, and was so fantastic that at the screening Mariska Hargitay decided to give her a part on SVU. That’s what I love! Women helping women. It was one of my favorite things that happened doing that show.

KEEP YOUR GIRLFRIENDS CLOSE
I learn my most important lessons not from books or experts, but from my girlfriends. I can’t hang out with women that aren’t honest and real. I can’t chit chat anymore. You go in and you go deep with me or I’ll see you at a cocktail party once a year. Women have a completely different way of—as my mother says—“shaking it out and laying it down.” Women can talk for hours about infidelity or fear of death or Botox—they can chew on something for so much longer than men. With Go Ask Ali I emphasize how important it is for women to help women and to share their stories because that’s really how we learn things.

SPILL YOUR BEAUTY SECRETS
A few years ago I got my eyes done to fix the bags under my eyes. The eye bags were my Moby Dick. It was a hereditary condition and not enough powder or lighting could fix it. I asked a bunch of women in LA, who I knew had done some cosmetic procedures, for advice and they acted like they didn’t know what I was taking about. When I did the surgery, I video blogged the whole thing and wrote an article for Elle magazine about it that kind of said, “What’s the big deal about admitting you had something done?” Everyone was acting like I had an abortion and it was the 1950s. The ironic thing is that more women talk to me about that than anything else I’ve done in my career!

DON’T HIRE A HOT BABYSITTER
I can’t believe I even have to say this or write this but some women are not getting the memo. When you’re on a diet you don’t go hang out in the bakery. Why tempt it?

GO ON A GOSSIP CLEANSE
I don’t gossip any more—unless it’s about a celebrity and then they’re fair game! I found that the gossip thing became commerce between people and I got so tired of talking about other people. I went on a gossip cleanse and I’m so much happier!

Ali Wentworth

DON’T BE BORING
My favorite quote is “Boring women seldom make history.” I like women that are risk takers, that speak their mind, that do things like create “Time’s Up!” or discover cultures in Mongolia. It’s okay to make a little noise! We never study historical female figures that did needlepoint-—we study the ones that flew the first airplane.

ALI’S SUMMER READING LIST

Go Ask Ali Book
Anatomy of a Miracle by Jonathan Miles
Don’t Let Go by Harlan Coben
Just the Funny Parts by Nell Scovell
Fire and Fury by Michael Wolff
Land of a Thousand Hills by Rosamond Halsey Carr

SECRETS TO A HAPPY MARRIAGE

Ali Wentworth1. Have a sense of humor. I am not married to Chris Rock, but George is a great audience. He laughs at everything I say and it seems to work well for us.
2. Have sex. I’ve said to friends before, “We’re all tired, but sex is the one thing you have with your partner and sometimes you have to push yourself a little bit even when you’d rather watch Homeland.
3. Go into marriage with the mentality that you are with this person for the rest of your life. There is no escape hatch. Every time you have a fight or a big issue you don’t go to the “divorce” thought, you go to the “I am in this forever, so how are we going to figure this out?” thought.

(opening image) Iro leather jacket, $1,200 and Vince floral pleated dress, $345, Neiman Marcus, The Westchester, White Plains, NY; Marc Cain sandal, $520, Marc Cain, The Westchester, White Plains, NY; Alexis Bittar necklace, $165, alexisbittar.com

Text by Holly Parmelee
Photographs by Danny Christensen
Styled by Jennifer Greene; Hair by Josue Perez using VoCê/TraceyMattingly.com; Makeup by Julie Harris using Tata Harper/TraceyMattingly.com