Ali Wentworth on parenting across the generation gap

Shondaland Staff

This essay is adapted from the “Generation Gap” chapter of Ali Wentworth’s new book, Ali’s Well That Ends Well: Stories of Despair and a Bit of Inspiration.


It’s a strange change when you become a parent of your parent. The people you feared to upset and disappoint suddenly become those vulnerable people who need your guidance and wisdom. And you no longer have to hide the smell of cigarettes on your breath. It is an abstract version of terrible friday.

For me, it’s very hard to see my parents as fragile. Maybe because deep in the guts of my psychological DNA, I still need their approval. But I think it’s more likely that I just don’t want them to die.

When I had the Covid, I was hit with a sense of mortality, certainly. It wasn’t so much that I thought I was going to die as the tragic death toll we were witnessing globally. I have a visualization trick that I fall back on when I feel panicked about the fragility of life. And it is this: I am a tiny spot on an asteroid flying through space — a spot without any meaning. I am a blip. And that makes me feel better. I am nothing and nothing matters. Hallmark should hire me.

Ali’s Well That Ends Well: Stories of Despair and a Bit of Inspiration

And when it comes to ego and the quest for immortality through your work? I remember gushing about the amazing Mary Tyler Moore, who I adored and my daughters had never heard of. Everything is ephemeral. Even if I won three Oscars and two Golden Globes, decades from now nobody would remember that. A decade. I can’t even remember who won an Oscar last year. However, I would still love the experience of holding the statuettes and sitting on Ryan Reynolds’ lap.

Like so many people my age, I was sandwiched at this time between aging parents and children just starting to grow up. And it’s a painful heart pinch in every way. To be a mother to my daughters, to be a mother to my mother.

And right there, toggling between flipping through catalogs of nursing homes and booking flights to see my daughter through college is the inherent struggle: being the rock.

I don’t believe in parenting books. There is no formula, no single solution. You do the best you can with the children you have, with the person you are raising them with (if there is another person involved), in the circumstances in which you live and the time in which you were born. …Some of the most extraordinary people I know came from the worst circumstances or were unloved, and yet these emotional difficulties can shape some of the most empathetic and phenomenal humans. Chris Rock said his bullying experience was “the defining moment in my life. … It made me who I am. He even credited the pack of boys who regularly “kicked me, spit in my face, and kicked me down the stairs” because those experiences not only helped him think quickly, but also fueled his will to succeed. . That being said, you never wish hardship on your children. I’m not going to drop my girls off in the forest with a Swiss army knife and a can of tuna to see if they find their way to safety. The school of tough love does not naturally suit me.

While my kids are ready to sail, all I can do is love them aside and give them the only advice I have. Whether met by deaf ears is up to them.

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So to my daughter in college and my youngest daughter on her heels, I offer you this:

Slow and steady. Don’t show up in a sparkly halter top and roller skates just because everyone wants to stand out. Stick to your hoodie and jeans. You will end up being seen. By your people.

Don’t judge your roommate. They’re more interesting than you might think, though — particularly if – they come from a place you’ve never been. And they will be your best friend for the first three weeks. You’ll cling to each other, mostly so you don’t have to eat alone in the dining room. Never forget this common goal and treat them with kindness, even if you separate.

When you go to parties, grab a plastic cup of soda and cranberry juice, or vodka, whichever you choose (and never lose sight of the cup), but don’t get so drunk you lose control. And you vomit on a stranger. Or yourself. Be the one they vomit on.

I realize that sex is part of college culture like pizza in Milan. But don’t eat more than one pie a night!

You will never again have the luxury and the time to be educated so freely. Take the course on gender and public policy or the intellectual history of exile. If you want to be a lawyer, take a painting class, and if you want to be a dancer, take a physics class.

Join clubs, sororities, and fraternities if you feel inclined, but don’t let them define you. And reach out to people who don’t run in your pack. Even though we as humans are safer in one tribe, there is so much to learn from other tribes, and this is how we expand our minds. And make better fashion choices.

Lean in discomfort. You grow and develop, which may seem thorny and graceless, but I promise the muscles you can’t see are getting stronger. Contentment does not make you grow; discomfort does.

Take a moment to lay in the grass, climb the mountain, jump in the lake, learn that subway system. Wherever your college is, be part of the ecosystem. And please wear a coat. Even if you are a sexy witch for Halloween twerk-or-treat party.

My mother has always given me such wise advice. “Don’t let the wolf come in through the door.” (Still not sure exactly what that means.) “When you’re down, close your eyes and think about Christmas.” And now I’m the person giving out the advice. I think I’ll always feel like the kid no matter the circumstances, but there’s something satisfying about giving a little wisdom back. I quote Rita Mae Brown to my mother: “Dying isn’t so bad. At least [you] won’t have to answer the phone.

My mother is the strongest, most wonderful person I have ever known. She’s accomplished, yes, but she’s a force that’s always true to herself and impacts everyone she meets. My mother can curtsy to the Queen of England in a Givenchy suit and feathered hat as easily as digging holes for tomato plants in her backyard in rural Maine.

I hope that when my children find themselves straddling the fence of caring for their children and me, they will build on the foundation that my mother and I provided. And that they will pass the plan on to their children.

I have worshiped her all my life. I always wanted to be her when I was growing up. And now I’ve grown. And she’s eighty-six years old.

To my spectacular and mature mother, I offer you this:

To walk. Move your body. You need blood circulation and muscles, otherwise you won’t be able to get to the post office or pick blueberries. And you don’t want to go to the mall with me? (Note to self: Move your body too.)

Hang on to your female friends. As long as you can. Because one day they all died. (You actually told me, I’m recycling it.) Your friends hold the oral history of your life.

Stay in control of your finances as long as you are sane, then legally assign responsibility to someone you trust. Maybe someone outside of the family. But not the one who mows the lawn.

Surround yourself with beauty, even if it’s just a jar of wildflowers. But when the flowers decay and the water in the vase smells of eggs and sewage, you can throw them away.

If you must take Norvasc for blood pressure, take it with a Klondike bar.

Remember your stories. Pass them on. Especially all dirty business.

You get to be the crazy old lady now! Take it to your advantage! Yell at the bratty kids, yell at the geese pooping on your lawn, tell the grocer he should give you the bruised apples for free…

Label your medications. Label your medications. Label your medications.

Tell me your secrets. I know you have them.

There is no reason to shout at television. I swear they can’t hear you.

You don’t have to take your nightgown off…but you really should.

No, you can’t have a puppy.

Stay curious. Keep reading books and being curious about the world. (I promise you I’ll go all the way to the Eleanor Roosevelt biography you sent me. It’s so many pages!)

And finally, no, you’re not driving. Everywhere.

Soon the generational wheel of fortune will turn again. And the arrow will point to me. And I will keep all the wisdom of my mother and be grateful for my daughters who will rock me. I hope that when my children find themselves straddling the fence of caring for their children and me, they will build on the foundation that my mother and I provided. And that they will pass the plan on to their children.


Ali Wentworth is the author of New York Times bestsellers Go ask Ali, Ali in Wonderlandand Fortunately Ali afterwards. She made a name for herself in comedy shows In living color, Seinfeld, Uppercase, nightcapand as a regular on The Oprah Winfrey Show. His film credits include Jerry Maguire, The real blonde, office spaceand It is complicated. She frequently hosts Live with Kelly and Ryan and hosts the Shondaland podcast and iHeartRadio Go ask Ali. Wentworth lives in New York with her husband, George Stephanopoulos; their two daughters; a mixture of dogs; and an obese dachshund.

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