This is 75: 'Happy Grownup' Hal Rubenstein Responds to The Oldster Magazine Questionnaire
"I don’t approach age as if I’m supposed to feel good or bad about it. Since it’s inevitable, why waste time fighting it?"
From the time I was 10, I’ve been obsessed with what it means to grow older. I’m curious about what it means to others, of all ages, and so I invite them to take “The Oldster Magazine Questionnaire.”
Sometimes you’ll find responses from writers, musicians, and artists you’ve heard of—like Kate Pierson, Neko Case, Rosie O’Donnell, Ava Duvernay, Jerry Saltz, Lucy Sante, Ricki Lake, Hilma Wolitzer, Elizabeth Gilbert, Judith Viorst, Cheryl Strayed, Deesha Philyaw, Chloe Caldwell, etc.—but more often it will be people (of all ages) you haven’t heard of, Humans of New York-style. (Check out all the Oldster interviews…)
Here, glossy magazine legend, author, and writer/host of The Happy Grownup newsletter/podcast Hal Rubenstein responds. -Sari Botton
PS If you’re enjoying the work I do here at Oldster, please consider supporting it by becoming a paid subscriber. 🙏
Hal Rubenstein is the creator, writer and host of The Happy Grownup, a weekly newsletter on Substack and bi-weekly podcast on Apple Podcasts and Spotify that celebrates the joy, challenges, discovery, and serenity possible in life after 50. He’s the author of eight books including the best-selling 100 Unforgettable Dresses (HarperCollins), and Paisley Goes with Nothing: A man’s guide to style (Doubleday). His most recent books are Dressing the Part: Television’s Most Stylish Shows and Street Art Icons: The Story of The Wynwood Walls (Assouline) He is one of the founding editors of InStyle Magazine, where he served as its Fashion Director for 15 years. He is the former Men’s Style Director of the New York Times Magazine, one of the founding editors of Details Magazine and 7 Days, founder and Editor-in-Chief of the cult classic Egg Magazine. He was a restaurant critic for both Details (8 years) and New York Magazine (7 years) and Interview (4 years), and a columnist for The New Yorker, Vogue, Elle, Interview, and Ocean Drive. He’s been a design and hospitality consultant for several brands. And he’s won numerous awards including the CFDA (Council of Fashion Designers of America) Lifetime Achievement Award. He is a board member of The Paul Taylor Dance Company.
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How old are you?
75.
Is there another age you associate with yourself in your mind? If so, what is it? And why, do you think?
My brain clicks in at about 47, but I have no problem accepting my age.
Do you feel old for your age? Young for your age? Just right? Are you in step with your peers?
Absolutely not. We grew up with such preconceived, bogus images of what old age feels like. In 1984, I watched Dustin Hoffman playing Willy Loman in Death of a Salesman, walking with such doddering, frailty it was a miracle he made across the stage to the kitchen table. Except Loman is only 63! I was 35 at the time and I remember thinking no way am I going to be like that at 65.
Sure enough, 75 is nothing like you think it’s going to be when you’re young and it’s terrific. However, I don’t approach age as if I’m supposed to feel good or bad about it. Since it’s inevitable, why waste time fighting it? Yeah, it’s a lot, but it’s also pretty darn fascinating to experience. As for my peers, I’m in step with the ones I want to spend time with.
We grew up with such preconceived, bogus images of what old age feels like. In 1984, I watched Dustin Hoffman playing Willy Loman in Death of a Salesman, walking with such doddering, frailty it was a miracle he made across the stage to the kitchen table. Except Loman is only 63! I was 35 at the time and I remember thinking no way am I going to be like that at 65.
What do you like about being your age?
That I’m alive! I love my breadth of knowledge and experience. I’m still more curious than ever, but I relish not having to prove anything. I just enjoy who I am to those who matter to me.

What is difficult about being your age?
Nothing is more delusional about getting older than thinking that you’re going to have time to “take it easy.” You may no longer have to strive in business, but aging well is hard work, demanding nonstop vigilance, awareness and fearlessness, plus you have to deal with a really weird dynamic—always being good to your body while it’s intent on betraying you.
What is surprising about being your age, or different from what you expected, based on what you were told?
I’m delighted by my level of energy, drive, eagerness to learn more, indifference to slowing down. I look at that Cialis ad on TV of a silver-haired couple sitting in soaking tubs, placidly gazing at a sunset and think, Who are these people, and why are they so dull? The reason why I call it “New Aging” at The Happy Grownup is that it is nothing like what we were told.
What has aging given you? Taken away from you?
It’s afforded me serenity, satisfaction, resignation, resolution and confidence. Time has taken away physical freedom, a carefree attitude towards health, friends and loved ones.
How has getting older affected your sense of yourself, or your identity?
Not that much, because I’ve been comfortable with myself for a long time.
I’m delighted by my level of energy, drive, eagerness to learn more, indifference to slowing down. I look at that Cialis ad on TV of a silver-haired couple sitting in soaking tubs, placidly gazing at a sunset and think, Who are these people, and why are they so dull? The reason why I call it “New Aging” at The Happy Grownup is that it is nothing like what we were told.
What are some age-related milestones you are looking forward to? Or ones you “missed,” and might try to reach later, off-schedule, according to our culture and its expectations?
I don’t think milestones have anything to do with age. Seismic events are not related to time as much as they are by curiosity, creativity, work you love to do, and the people you love to be with.
Also, I don’t think you should live your life waiting for “big” moments. One of the best things you learn getting older, is that the moments that move you the most are often “small.” Gestures of kindness, moments of affections, the right touch, hearing a quietly whispered secret that reminds you how lucky you are to have a certain person or people in your life. And as you get older you appreciate them more than anything else.
I’ve had more than my share of “big” moments—marriage, magazines launches, books published, Woodstock, Vietnam war protests, the Millennium, my niece’s graduation, seeing E.T: The Extra-Terrestrial on opening day. Now, life’s more about experiencing what’s so special about every single day. Unfortunately, we’ve directed our culture to believe that everything happens in “big” moments, hence our wrongheaded obsession with turning every occurrence into ‘Breaking News” and setting up endeavors to fulfill “expectations” rather than leaving yourself open to the excitement of whatever happens. “Expectation” may be one of the most dangerous words in the English language and one that should be eliminated from your vocabulary and mindset.


What has been your favorite age so far, and why? Would you go back to this age if you could?
I loved my 40s and 50s. It was an era of high energy, fearlessness, and hunger for the unknown. So many willing to take a risk on a passion.
We’ve kind of squelched that today. We’ve let too much doubt creep into our decisions, and pay attention to too many people sticking their two cents in. Social media has not been a friend to adventurousness. We need to shut out the dispiriting noise and listen to our guts and instincts.
But I don’t believe in going back. Because you can’t. Past events can’t be duplicated. Besides, going back is a perfect example of doing something with expectation. No way. That’s why my favorite time to be alive is right now. Today. I’m still here. If that’s not a reason to celebrate, what is?
I don’t think you should live your life waiting for “big” moments. One of the best things you learn getting older, is that the moments that move you the most are often “small.” Gestures of kindness, moments of affections, the right touch, hearing a quietly whispered secret that reminds you how lucky you are to have a certain person or people in your life. And as you get older you appreciate them more than anything else.
Is there someone who is older than you, who makes growing older inspiring to you? Who is your aging idol and why?
I don’t have idols. Don’t put people on pedestals. That’s not fair to anyone. That said, thanks to a year of podcasts, I’ve met so many incredible New Agers with vibrant lives. Model activist Bethann Hardison, beauty mogul and now best-selling author Anastasia Soare, entrepreneur Daymond John, chef Jean-Georges Vongerichten, journalist and author Linda Ellerbee, designer Norma Kamali, film genius Stephen Spielberg, Broadway composer John Kander who at 96 and still producing shows and seeing his works like Cabaret and Chicago celebrated. It’s an exciting time to be growing older. Now the culture has to catch up and realize that New Agers have so much to give and there’s so much you can learn from us.

What aging-related adjustments have you recently made, style-wise, beauty-wise, health-wise?
You pay close attention daily to all of the above. You must exercise regularly, not to have 18-inch arms, but so that you can move. You have to keep reminding your body that you are in charge and need it to work with you rather than be an ally of gravity.
Take care of that skin, that hair, those teeth! In your youth, your skin is so dewy it practically leaks water. No pill, injection or operation will ever bring that back. So you have to devise a skin routine for yourself. Go online, read, research, talk to your dermatologist, talk to the kids working at Sephora, reach out to gather the information and ammunition you need to maintain the best version of you.
Happily, the options are now greater than ever at every price point. You can spend tens of thousands on surgeries, or hundreds on effective skin care lines like Dr. Sturm, Cible, and Augustinus Bader that work, or so much less on impressive mass brands like No. 7 Beauty. Invest what you can, but make sure you do what you can for your skin to glow.
Enjoy great food and stay away from junk, get a good night’s sleep, drink water, and most importantly, surround yourself with people who lift you up. That’s the best advice anyone can give you for keeping a smile on your face, and sparkle in your eyes.
What age related adjustments do you refuse to make and why?
You have to adjust. You can’t dig your heels in. I guess the only adjustment I refuse to make is declaring “I’m too old” as an excuse for not doing something.
What turn of events had the biggest impact on your life?
There isn’t one defining moment. There are lots of them. My mom bringing my sister home from the hospital on my 4th birthday, which is still my best present ever. My Bar Mitzvah. Coming out at 17. Discovering the paradise that is Fire Island. Disco (I loved it). Being diagnosed as HIV positive. Helping to found Details Magazine, which become the Bible of downtown in the 80’s. Malcom Forbes backing me to create Egg Magazine. Being hired as Men’s Style Director of The New York Times, my first job in fashion. Being a founding editor of InStyle, the industry shaking magazine that made fashion truly accessible, serving as restaurant critic of New York Magazine. Launching a clothing line HSN. Becoming a best-selling author. Winning the CFDA Founder’s Award for a lifetime of devotion to living well. Launching The Happy Grownup. And most importantly, meeting my husband David Nickle 29 years ago in a chatroom on America Online back when no one discussed online hookups above a hush. And there may be so much more to come.
My mom always said that you should leave the house expecting to run into someone you went to high school with. It may initially sound superficial, but always putting your best self out there instills self-worth. Pride is not a sin. Modesty is an overrated virtue. At this point in your life, pop your buttons. Don’t walk into a room. Make an entrance. You’ve earned it.
What is your number one regret in life? If you could do it all over again, what is the biggest thing you’d do differently?
I wish I had learned how to play piano. But except for that, regrets are a waste of energy. Perhaps the results would have been different if I’d had more self-confidence when I was performing. I’m sure there were opportunities I shouldn’t have shied away from, chances that might have been worth taking, but looking back on woulda-shoulda-coulda is fruitless. The only worthy direction you look to is forward.
What is high up on your “bucket list?” What do you hope to achieve, attain, or plain enjoy before you die?
Hate to be contrary but I don’t have a “bucket list.” I’m not looking to bungee jump over Victoria Falls. I’m lucky. I’ve done so much of what I’ve wanted to do, my bucket is pretty full. There are still places I want to travel to, like Angkor Wat, but without sounding arrogant, I’ve been given the opportunities to achieve so much, I have nothing left to prove.
That doesn’t mean there aren’t still things I’m eager to accomplish. I want The Happy Grownup to become a go-to destination for millions of New Agers over 50, offering uplifting, doable advice and insight for celebrating the second half of one’s life. The more you discover how much joy that’s still possible, the better equipped you’ll be to face the challenges that we’ll inevitably face as time now goes breathlessly fast.

Is there a piece of advice you were given, that you live by? If so, what was it, and who offered it to you?
My mom always said that you should leave the house expecting to run into someone you went to high school with. It may initially sound superficial, but always putting your best self out there instills self-worth. Pride is not a sin. Modesty is an overrated virtue. At this point in your life, pop your buttons. Don’t walk into a room. Make an entrance. You’ve earned it.
What are your plans for your body when you’re done using it? Burial? Cremation? Body Farm?
Jews does not supposed to be cremated, though I would prefer it, which means I may be spending eternity at Cedar Park/Beth El Cemetery in Paramus, New Jersey. We will see.
Hate to be contrary but I don’t have a “bucket list.” I’m not looking to bungee jump over Victoria Falls. I’ve done so much of what I’ve wanted to do, my bucket is pretty full. There are still places I want to travel to, like Angkor Wat, but without sounding arrogant, I’ve been given the opportunities to achieve so much, I have nothing left to prove. That doesn’t mean there aren’t still things I’m eager to accomplish. I want The Happy Grownup to become a go-to destination for millions of New Agers over 50, offering uplifting, doable advice and insight for celebrating the second half of one’s life.
What do you expect to happen to your “soul” or “spirit” after you die?
Not surprisingly, I have no expectations about what happens to my soul or spirit, so it will be a surprise, though I do hope I don’t have to learn how to play the harp.
What’s your philosophy on celebrating birthdays as an adult? How do you celebrate yours?
Ignoring your birthday is ridiculous! Why would you do that? It’s not like you’re stopping time by ignoring it. No. No. No. My birthday is MY holiday, my individual Christmas starring ME, and it needs to last at least a week. Bring ‘em on. Keep ‘em coming. And don’t forget to buy yourself a gift.






The best line ever: "I look at that Cialis ad on TV of a silver-haired couple sitting in soaking tubs, placidly gazing at a sunset and think, Who are these people, and why are they so dull?" Bless you, Hal Rubenstein, and amen!
One of my all time Oldster favorites!!
I love your exuberance! About the learning to play piano regret, why not start now? I started learning violin at 68, three years ago. Got a teacher. Practiced some each day. I can actually play with some intention now.