28 Comments

Hey Kasra, I see many young people (I’m 54) lamenting struggling with friends. A couple things I’ve observed:

-It’s harder to make friends in big cities. With so many options for things to do, meeting with you is just 1 of many options.

-Big cities tend to be more transient. Many people try NY or LA etc because they are definitely exciting places to be but they can be harsh in a variety of ways that causes people to leave.

-Age matters. In your 20s/30s many factors contribute to losing friends: job changes, going back to school, marriage, having kids. This does get better in your 40s as people’s lives stabilize again

-Give up trying to replicate what you had in high school/college dorm. Those were unusual physical proximity/frequency environments that are nearly impossible to replicate as adults

-If you find even one person you REALLY resonate with, put more effort into that person, 1 awesome friend is better than 50 acquaintances. The kind of person you call in an emergency.

-By the time they’re 50, most men do not have any close friends, take this warning seriously, it’s an absolutely miserable feeling realizing that fewer and fewer people would come to your funeral. Invest now because…

-Time spent together matters. You can have one amazing outing but if you only do that once a quarter it doesn’t feel like a friend. I’ve found 2x a month feels like the minimum. In person preferable but call if not.

-Don’t look to marriage to solve loneliness. Your spouse and later kids will become your primary relational world, but many married people are lonely too, plus your spouse can’t meet all your relational needs. You need friends outside the marriage.

I wish you the best,

Dave

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thank you so much for this comment Dave!

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great post as always. and it was published at the *exact* moment I was thinking about how I feel like my time in ny is coming to an end soon—for reasons not yet completely obvious to me, because much like you, ny has been fantastic to me in many ways. maybe it’s just this stage of life (late 20s & early 30s)!

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thanks sundus! looking forward to hearing what you decide and always happy to chat

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Great reflective post! I personally blew up my life in nyc and moved to Miami for a job only to realize that I love NYC more than anything. You're correct that it's a reversible decision for remote workers. I've found for myself that hosting intentionally small gatherings with people I really enjoy has been the most fulfilling solve for the natural loneliness of inhabiting packed spaces of albeit interesting people. Best of luck to you in your new chapter :)

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thank you Elliot! agreed, small gatherings with close friends feels like the right move, planning to do more of that

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Thanks for sharing your thoughts in this piece. Have enjoyed your pieces in my inbox.

FWIW, what you describe wanting 'long-term friendships and stability' is part of why I ended up leaving San Francisco. It's a very transient city. I realize the irony of leaving a transient city haha. Of the group of say 50-70 friends and acquaintances who I knew there in 2011-2013, I think roughly 2-5% of them were still there 5 years later. The ones I know who are still there had to make huge tech money and/or sell a company to be able to buy a house. I'd recommend the east bay if you're looking for somewhere less transient.

But yeah, I can totally relate to having multiple disparate groups of people who don't quite gel. Having to schedule people out for an hour hang 3 weeks ahead of time. etc. I remember reading about the term 'planshopping' in a Tim Ferriss book (who lived in SF for a long while). [Planshopping - That is, deferring committing to any one plan for an evening until you know what all your options are, and then picking the one that’s most likely to be fun/advance your career/have the most girls at it—in other words, treating people like menu options or products in a catalog.]

The East Bay is still fairly transient but people stick around a lot longer. I'm also finding it's easier in my 30s to find people who are down for long chill frequent impromptu and satisfying hangs.

I wish you the best of luck in SF.

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thank you! yea I can really see that dynamic in SF too

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what a profoundly reflective note, Kasra! I haven’t lived in nyc but in my 4ish dipsticks, I’ve felt very similarly about the city. I plan my friend-dates a week in advance, people are mostly double booked and I’ve missed the “hey let’s hang in a few and see where the day takes us?” except on one occasion. The energy and diversity is always fascinating and at times, overwhelming.

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thanks for reading Lakshmi!

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Reading this reminded me of my own almost life-long struggle to find a circle of friends where I truly feel at home—where loneliness isn’t something I carry with me. The way you described your time in New York, being so socially active—with hundreds of friends, events, and communities—only to ultimately find it unfulfilling really resonates with me. It’s disappointing, but not because of you or your journey. Rather, it’s made me reflect on my own situation, and I can’t help but feel embarrassed and upset about where I am in comparison. (with a sigh of sorrow in the end)

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I get you ❤️ but still you've made a lot of valuable friendships over the years, and you've also made some big changes to your life that most people would be too afraid of doing. there's still many decades to make close friends, and the journey never stops :)

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awesome read, I feel like you put into words what I was thinking about for a while.

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Very interesting and relatable. Do you think this is truly inherent to NYC or a symptom of an overall trend in modern life? Do you think it would be possible to "blow up" and start anew in NYC? like any practical advice to make things work there, or just not possible?

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great questions. I definitely think it's a general thing – some cities might be more transient/fast-paced than others, but you'll run into it everywhere, especially for people in their 20s/30s.

one way it's possible to "blow up" and start anew in the same city is just to leave for a while and come back. I'm not sure of other ways – it's hard to overcome inertia in your existing habits and routines without shaking things up a lot.

the main practical advice for NYC (or any city) is just: create (or find) strong social rituals – weekly dinners with the same people, clubs that involve a shared hobby, etc. keep investing in the people who do show up consistently, rather than always going for breadth & novelty

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super crazy! I was *just* about to post a similar story about myself. i lived in nyc for 10+ years and while i made amazing friends, and fun acquaintances, a lot of what you said resonated with me. I recently moved to CT (not quite as far as SF).

My challenge with nyc is there is too much of a cultural focus on being *busy* and *surface* things over depth of conversation. of course, with the right group of people, that can be fun in its own way. however, i’ve really struggled to feel at home.

the fun and excitement was awesome in my 20s, it doesn’t do it in my 30s. Will sign up on your forms for events and hopefully will meet you IRL one day!

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thanks for reading!

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good friends and community can be hard to find all across the world (I'm in New Zealand!) but they are there - sometimes just not exactly how you might want them. I agree with a comment below about how proximity can drive relationships in college/university but I think this is true as we get older as well, such as neighbours or people who live in your suburb as you more often see them over and over again. It can be hard to build such a community when people are so busy. I hope SF continues to work out well.

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thanks Jana!

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miss u <3 u

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Such a great post that made me realize how deep you are in your friendship and definite about what you want in your relationship!

I appreciate your honesty and bravery in your relationship and thinking about life!

Love

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This resonates on so many levels. I similarly yearn for the small friend group that regularly hangs out every week, if not multiple times a week. There's a genuine sense of living life together rather than catching up on life.

Excited for you in this next chapter and looking forward to seeing you in SF soon :)

+1 for blowing up your life - highly recommend

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loved this, thank you for sharing!

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NY sounds like a similar vibe to London, with people scheduling things months out for an hour of conversation.

I find it really frustrating, but wouldn't know where to find something better in the UK, also I do have some communities I would struggle to leave

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it sounds like the type of relationship dynamic you’re looking for is good roommates

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