What does it feel like to "lose your looks" to age?
10.06.2025 01:07
My old pictures, even the ones I liked and used for online profiles, are a much heavier version of me. If I ever went out on the dating sites again – I won’t – but if I did, people would be surprised to meet me. “You’re nothing like your photos,” they would say. “I expected you to be… fat.”
Being lighter gives my bounce back. I’ve adopted a new look, Hawaiian shirts and a panama hat. I have a lot of energy for a sick person.
I dated enough drop dead gorgeous (and smart, talented, successful) women in my 20s and 30s to fill a book. Enough for my book at least. One told me in all sweetness and vulnerability that she’d never dated a good looking guy before me and didn’t know what to do. That memory is a page for my book. Years later I showed a picture of my younger self to some guys I was working with and they said something like “wow”. Another snapshot, page 172.
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I was still hanging with kids half my age but these were tech guys, company founders and CEOs, inventors. If you walked into the room you would notice them but not me, not until you thought “who’s that older guy in the corner” and you would probably mistake me for a venture capitalist.
Why should I care how I look?
At this 110-year-old SF spot, the burger is famous but the owner wants to be president trib.al/OT4KS…
I like it, I think I’m looking pretty good now. I don’t know if I really am and frankly I don’t care. I’m at the end of my book and it was a good one… a little shallow at first, a little slow and bleak in the middle, but a nice ending that makes you think. And pictures, lots of wonderful pictures in my book, unforgettable moments.
I can’t tell you what happened but I kind of grew into that look.
My wild years, a long off topic story
I was a shy, bookish, and unnoticeable kid in the 70s and early 80s before there was anything cool about being a nerd. I wasn’t fit, a dweeb with no fashion style. More to the point I was childlike and inoffensive, didn’t know how to talk to men or women. The popular boys and girls considered me “cute”, not a manly man for sure. I sometimes got a kiss on the cheek, but not exactly what they were looking for in a mate or companion. But I played piano was super good at taking tests. “I’ll see you at the Van Cliburn one day” one older woman wrote me.
I observed my father, who in his forties and early 50s had a very smart look or so I thought, in kind of a dignified European businessman way. He approached the world fearlessly – not aggressively but he knew who he was and did not hesitate. Girls behind the register, the bank counter, the museum volunteer station would flirt with him and he would just be himself.
I lost my looks and regained them more than a few times though never all the way fugly or stand-out guapo — sometimes in the space of a day. Haven’t we all?
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By the time I retired from the scene in favor of business and other serious pursuits I was middle aged and fat. Not American-level fat, more like an active plump blob, 50+ pounds overweight. The weight made my face look younger but not in a good way. You can see that in my Quora profile picture, which is about 4 years old now.
One of the benefits of cancer is that you can lose a lot of weight. I’m down 60 pounds, back to the trim body shape I had as a young man. If you squint I look just right. But the chemicals can dry you up, shrivel your skin, make wrinkles and little red spots. And you can feel just awful.
I carried that mojo into my forties, going on a dating spree after a divorce despite gaining a few dozen pounds. A hot and spicy roommate / houseguest of mine said something about plain looking people like me not getting invited to parties unless we had something to offer. Rich guys and cocky posers pretending to be rich would invite her to Marin, Napa, Silicon Valley for town-and-country pool parties, winery openings, band afterparties, rides on boats that never came. She made it clear I wasn’t on the invite list.
Got sick
Earlier, plain
I don’t know, I just didn’t care. I’ve lost a lot of things – loves, family, friends, money, homes, confidence. Religion, meaning, direction in life. And gained new ones, sometimes deeper and more mature things to replace them.
If you know you’re good looking, you are. If you truly don’t care about looks, good for you.
A cocky 20-something guy who was hitting on my roommate at one of these parties asked her “who’s the old guy”, not realizing she and I were the same age. “How old do you think I am,” she asked. I’d never been the old guy before, that hit me hard.
It’s annoying but not the worst thing ever.
The fat years
In that era we called it “the scene” and there was just one of them in San Francisco… or maybe two, one for younger people like us and the other for the old money set. They both intersected every night at the window tables and sidewalks outside a notorious restaurant called the Balboa Cafe.
Looks to me are how you project feelings. It’s about the audience, not an objective thing. To a dog we’re all beautiful; your cat knows you’re ugly but she’ll put up with you. The most important audience is you. Internally it’s all about confidence, poise, claiming your place in the world as a person, taking care of yourself.
(image: I don’t know if he’s good looking but he has the look – Vincent Noiseux has a killer smile and dances like he means it. For the old timers that really is Herb Alpert and his wife of 50 years Lani Hall at the end of the video)
So I’d hustle my network and show up anyway just to see the look on her face to find me sitting on the couch when she arrived. The catered food, DJs, live bands, views out the window, models, designers, paid photographers, butlers in tuxes with trays of pre-poured champagne, cheerleaders from the local sports team, all an added bonus. It wasn’t exactly a burden. The unnecessary drama was. It got old, like me. It felt unreal, like living in a reality show fueled by lots of cocaine and bad behavior, which I observed for my book but did my best not to partake.
I should care because that reflects how I feel about myself. You only have one body in this world and one chance at life. Best you take care of it.