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I moved from Chicago to Los Angeles in my late 60s, hoping for a fresh start. I found it hard to make friends and felt out of place.

August 6, 2025
in News
I moved from Chicago to Los Angeles in my late 60s, hoping for a fresh start. I found it hard to make friends and felt out of place.
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woman stand in front of topa mountain winery welcome sign
Julia Bailey visiting a winery in Ojai.

Courtesy of Julia Bailey

I didn’t decide to move halfway across the country on a whim. I had been thinking about leaving Chicago for the cool vibe, gorgeous weather, and beautiful, sprawling landscape of Los Angeles for many years.

With its sunshine and palm trees, Los Angeles promised a new beginning, and as a freelance writer nearing her 70s, that’s exactly what I was looking for. I hoped for a fresh perspective and maybe even some new clients.

So in 2022, I took the leap and rented a beautiful old Mission-style home in West Hollywood with my daughter and son-in-law.

We arrived just as the purple jacarandas were blooming and the air was soft and fragrant. I spent days writing outside, surrounded by nature, and taking long walks to bookstores and cafés.

It was just as I’d imagined, but then came the culture shocks.

Being in a city of millions felt surprisingly isolating

work space
Bailey’s home office in West Hollywood.

Courtesy of Julia Bailey

I didn’t expect it to be easy to start over at my age, but I also didn’t expect it to feel quite so lonely.

Making new friends in your late 60s and early 70s is like trying to join a book club that’s been meeting for 40 years. Most people my age already have their lives set with established circles and routines.

In Chicago, my friendships had grown slowly and steadily, mostly with people I’d met at the marketing agencies I’d worked for over the years.

Where was I to go to meet new people here, especially without my own car or a built-in community?

The days stretched on. I kept working, walking, hoping to find my people. Los Angeles, however, just was not built for chance encounters, from what I could tell.

I didn’t vibe with the culture in Los Angeles

inside of library looking out over green lawn and west Hollywood landscape
Inside the West Hollywood library, where Bailey sometimes worked.

Courtesy of Julia Bailey

I grew up in the Chicago area where, in my experience, people typically have a no-nonsense attitude, dry wit, and willingness to say what they think. That’s not what I found in Los Angeles, which runs on a kind of curated optimism.

Everywhere I turned, I heard lines like “anything is possible here” or “you can be whoever you want to be.”

That’s fine, but in Chicago, we temper our dreams with dark humor and talk about our struggles like they’re everyone’s business. That attitude can be a social liability in Los Angeles.

And because I’m older and set in my way of thinking, my Midwestern mindset made me feel out of step.

I’d walk past wellness centers and juice bars with “Good Vibes Only” signs, feeling disconnected.

LA’s food scene also left a lot to be desired for me

person with fork and knife in a colorful green and orange vegan salad
Bailey missed deep-dish pizza while living in Los Angeles.

Oscar Wong/Getty Images

When it comes to vegan options, I will give it up for Los Angeles. There are plenty. But pizza? Forget it. You won’t find a decent deep dish anywhere.

I’m not a foodie, but $20 salads and overwrought concepts got old fast for me.

I missed the no-nonsense food culture of Chicago, where nobody judges you for ordering a Polish sausage and nobody serves you one on a gluten-free bun with pickled fennel.

In Los Angeles, food often felt like performance art. I just wanted dinner.

I left Los Angeles shortly after arriving

Eventually, I stopped pretending things were fine, and I stopped blaming myself for not fitting in.

The truth is, Los Angeles and its surroundings can be magical. Wineries, new-age outdoor restaurant venues, and beautiful libraries with exceptional views are just some of its many treasures.

However, for me, the city was also a mirror, reflecting back how much more rooted I feel in Chicago with all kinds of people, attitudes, and seasons.

I didn’t fail at starting over. I just learned that starting over in the right place and with the right people matters more than I thought.

Los Angeles didn’t give me the reboot I expected, but it did give me clarity. And at my age, that’s more than enough.

I’ve since decided to return to Chicago, this time with more self-knowledge and fewer illusions. I’m not retreating. I’m reclaiming what I truly value.

The post I moved from Chicago to Los Angeles in my late 60s, hoping for a fresh start. I found it hard to make friends and felt out of place. appeared first on Business Insider.

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