About us
Hi there! We're Difficult Friends, a community-run arts & humanities club: Website ⟡ Instagram ⟡ Venmo
We empower Austinites to tackle Difficult ideas and projects.
Our core values are:
- creative growth,
- intellectual challenge,
- human connection, and
- civic imagination.
Our events are designed as intellectual workouts! And creative experiments! We host workshops and discussions that push Austin residents to think harder thoughts, make cooler stuff, and connect more deeply across their human differences.
This is not an organization for the faint of heart. As our name suggests, we take pride in being Difficult Friends and in confronting Difficult challenges.
Meaning is Difficult! Embrace the Difficult!
Difficult Friends just launched in April 2026! So we're very excited to see all of y'all here. Welcome to this new group!
Our Philosophy of Friendship
There are things that can only happen between people really being themselves with each other.
Not performing, not managing, not carefully calibrating what they show.
Wholehearted creative collaboration is one of them. Real intellectual encounter is another. The kind of friendship that actually sustains people through difficulty is a third.
We think it’s good to be a Difficult Friend.
Friendship itself is difficult to the degree that it is both genuine and built across difference. You will find our events creatively and intellectually challenging. They will put you in touch with people in ways that are energizing but unfamiliar.
But Difficult Friends are friends worth having.
And please consider donating to us through Venmo or our Meetup page. It really makes a difference.
Statement of Welcome & Inclusivity
We believe everybody can be Difficult. ;-)
Difficult Friends is an inclusive community space, and we particularly seek to protect and welcome our LGBTQIA+, queer, transgender, and nonbinary members. Event attendees may be asked to share their preferred pronouns and will be asked to respect the preferred pronouns shared by other participants. Women, immigrants, people of color, religious minorities, people with disabilities, and neurodivergent folks seeking a diverse community are also especially encouraged to attend!
That said, no particular identity performance is needed, desired, or expected from our Difficult Friends. Come as you are and know you have a seat at our table, no matter how life has brought you into our community.
Our Unique Session-Based Structure
Difficult Friends is a group designed to incubate close creative & intellectual friendships. We run themed short-term and long-term sessions featuring outings, workshops, and discussions connected by a core concept.
It’s like a semester-long class, but shorter (or in some cases, much longer)!
However, each our events is also able to stand on its own! So you should feel free to come by whenever, regardless of your attendance at prior events. We welcome first-timers always. Members are also free to drop in and out of Difficult Friends. We encourage everyone to feel a sense of freedom and lightness while doing as much or as little with the group as they please.
In the interest of being Difficult, we also reserve the right to host occasional random one-off events just for funsies!
Featured event
Drake X Impressionism ⟡ THE BREAKDOWN ⟡ Pop Culture X Art History ⟡ ATX Artists
Join us for THE BREAKDOWN: a bar lecture series where ATX artists explain their favorite artworks, covering everything from deep dives into Renaissance sculpture to nuanced takes on the best of pop culture.
Our Inaugural Set of Topics: Soft Light & Soft Boys ⟡ Understanding The Impressionists & Drake
From June-July, the theme of our arts & humanities club is "The City," Although at first glance, painters like Claude Monet may seem to have little in common with Aubrey Graham, these artists share a deep commitment to portraying urban life and the myriad complexities of being out in the streets.
In Drake's own words:
Shakiness, man, I don't have no time for that
My city too turned up, I'll take the fine for that
This been where you find me at
That's been where you find me at
Come join us to better understand the "Views" of these exceptionally influential modern artists.
Your Presenters For THE BREAKDOWN: Rachel & Sean
Sean Saldaña is a KUT News reporter who has presented his archival research and oral storytelling at venues like Bass Concert Hall, in addition to appearing regularly on Austin's public radio and formerly on NPR. A native Austinite and Texas Ex, Sean moonlights as a stand-up comic and is currently competing in Cap City Comedy Club's 'Funniest Person in Austin' Contest.
Rachel Summer Cheong holds an A.B. in the History of Art and Architecture from Harvard College. A multidisciplinary artist and cultural organizer, her work has been used by magazines like Vox and Verdict, as well as cultural institutions like the New York Philharmonic and local non-profits like Move Texas. She loves taking photos, going dancing, and organizing whimsical free events.
Event Structure
Come join us at Darwin's Pub on Tuesday, June 23 from 7-9 PM for two short lectures on The Impressionists and Drake, followed by audience Q&A and an open mixer with the presenters. Attendees will be provided with post-its on which to doodle during the talks and write down their thoughts from the event.
Audience members will also be able to vote on whose art they appreciate more: The Impressionists... or Drake?
Our Theme for June & July: The City
Every 1-3 months, our group chooses a special theme to explore in our events. This writing workshop is part of our June-July session on "The City." How do we make the decision that it's worthwhile to live or leave somewhere? What does our city owe us and what do we owe it back? What does it mean to "Keep Austin Weird"? How do art and literature expand or limit our sense of civic possibilities? What new kinds of cities and city life can we imagine? And how will we know when this city has become ours?
These are some of the questions we hope to investigate this month, while offering Austinites a creative home in our own arts & humanities community.
About Us
This group is a project by Difficult Friends, a community-run arts & humanities club: Website ⟡ Instagram
We empower Austinites to tackle Difficult ideas and projects.
Our core values are:
- creative growth,
- intellectual challenge,
- human connection, and
- civic imagination.
Our events are designed as fun intellectual workouts and creative experiments. We host workshops and discussions that push Austin residents to think harder thoughts, make cooler stuff, and connect more deeply across their human differences.
This is not an organization for the faint of heart. As our name suggests, we take pride in being Difficult Friends and in confronting Difficult challenges.
Meaning is Difficult! Embrace the Difficult!
Statement of Welcome & Inclusivity
Here at Difficult Friends, we believe everybody can be Difficult. ;-)
Difficult Friends is an inclusive community space, and we particularly seek to protect and welcome our LGBTQIA+, queer, transgender, and nonbinary members. Event attendees may be asked to share their preferred pronouns and will be asked to respect the preferred pronouns shared by other participants. Women, immigrants, people of color, religious minorities, people with disabilities, and neurodivergent folks seeking a diverse community are also especially encouraged to attend!
Photography Policy
The event organizers of this meetup may take photos or videos of our events. By attending this event, you consent to being filmed and photographed. (If it’s Rachel, don’t worry - she will airbrush any blemishes & imperfections xoxo)!
Upcoming events
8
Modern Loneliness ⟡ Philosophy Book Club ⟡ The Need for Roots by Simone Weil
Central Market - North, 4001 N. Lamar Blvd., Austin, TX, US"To be rooted is perhaps the most important and least recognized need of the human soul." – Simone Weil, The Need for Roots
Written in 1943 as a blueprint for postwar reconstruction in France, The Need for Roots argues that the deepest wound of modern life is déracinement (uprootedness). In Weil's view, modern cultures create a profound spiritual void: human beings suffer because they no longer feel they belong anywhere, to any specific place or people.
Urban development sits uneasily within Wei's philosophical worldview, which is why we're reading this book as part of our June-July session on "The City." Weil saw the modern metropolis as one of the great engines of déracinement: pulling people away from the rhythms of the soil, dissolving regional cultures into a thin national soup, reducing workers to interchangeable widgets, and substituting empty transactions in place of the bonds of shared history, craft, and inherited meaning.
But Weil also knew that abstract nostalgia for the village was no answer, and her constructive vision asks something harder of any community, urban or otherwise: that it offer its members concrete obligations, sacred ordinary work, and a culture they can actually inhabit rather than merely consume.
Read against a city like Austin, the book offers us a sharp set of questions rather than a verdict. What would it take for a city re-forming around transplants, remote/gig workers, and rapid turnover to grow roots rather than to dissolve them? What civic institutions—community groups, neighborhoods, organizations, political movements, rituals, friendships—actually root people, and which only simulate rootedness while leaving the underlying alienation untouched?
Weil enriches the vocabulary of contemporary urbanism with language for the needs of the soul. Come join us to read her work and discuss its relevance for Austin.
Our Theme for June & July: The City
Every 1-3 months, our group chooses a special theme to explore in our events. This philosophical book club is part of our June-July session on "The City." What does it mean to "Keep Austin Weird"? What does our city owe us and what do we owe it back? How do art and literature expand or limit our sense of civic possibilities? What new kinds of cities and city life can we imagine? And how will we know when this city has become ours?
These are some of the questions we hope to investigate this month, while offering Austinites a creative home in our own arts & humanities community.
Location
We'll be meeting at Central Market on N. Lamar! Most likely on the upstairs patio accessible through the inside cafe stairs.
About Us
This group is a project by Difficult Friends, a community-run arts & humanities club: Website ⟡ Instagram
We empower Austinites to tackle Difficult ideas and projects.
Our core values are:- creative growth,
- intellectual challenge,
- human connection, and
- civic imagination.
Our events are designed as fun intellectual workouts and creative experiments. We host workshops and discussions that push Austin residents to think harder thoughts, make cooler stuff, and connect more deeply across their human differences.
This is not an organization for the faint of heart. As our name suggests, we take pride in being Difficult Friends and in confronting Difficult challenges.
Meaning is Difficult! Embrace the Difficult!
About Your Host
I'm a writer and photographer living in Austin with my dog, Cookie. You can find out more about me and my work here: https://rachelsummercheong.com
I've been busy working on my first novel, but I hope to get around to doing more with Substack this summer as well. https://substack.com/@rachelsummercheong
— Rachel
Statement of Welcome & Inclusivity
Here at Difficult Friends, we believe everybody can be Difficult. ;-)
Difficult Friends is an inclusive community space, and we particularly seek to protect and welcome our LGBTQIA+, queer, transgender, and nonbinary members. Event attendees may be asked to share their preferred pronouns and will be asked to respect the preferred pronouns shared by other participants. Women, immigrants, people of color, religious minorities, people with disabilities, and neurodivergent folks seeking a diverse community are also especially encouraged to attend!
That said, to quote the progressive labor activist Maurice Mitchell, we do not accept “using one’s identity or personal experience as a justification for a political position. You may hear someone argue, ‘As a working-class, first-generation American, Southern woman…I say we have to vote no.’ What’s implied is that one’s identity is a comprehensive validator of one’s political strategy—that identity is evidence of some intrinsic ideological or strategic legitimacy. Marginalized identity is deployed as a conveyor of a strategic truth that must simply be accepted. Likewise, historically privileged identities are essentialized, flattened, and frequently—for better or worse—dismissed.
To be clear, personal identity and individual experience are important. And while it is true that the ‘personal is political,’ the personal cannot trump strategy nor should it overwhelm the collective interest. Identity is too broad a container to predict one’s politics or the validity of a particular position... One’s racial or gender identity, sex, or membership in any marginalized community is, in and of itself, insufficient information to position someone in leadership or mandate that their perspective be adopted.
People with marginal identities, as human beings, suffer all the frailties, inconsistencies, and failings of any other human. Genuflecting to individuals solely based on their socialized identities or personal stories deprives them of the conditions that sharpen arguments, develop skills, and win debates. We infantilize members of historically marginalized or oppressed groups by seeking to placate or pander instead of being in a right relationship, which requires struggle, debate, disagreement, and hard work. This type of false solidarity is a form of charity that weakens the individual and the collective. Finding authentic alignment and solidarity among diverse voices is serious labor. After all, ‘steel sharpens steel.’”
For a concise summary of my views re: identitarian politics as this meetup’s lead organizer, feel free to refer to his excellent article Building Resilient Organizations.
Photography Policy
The event organizers of this meetup may take photos or videos of our events. By attending this event, you consent to being filmed and photographed. (If it’s Rachel, don’t worry - she will airbrush any blemishes & imperfections xoxo)!11 attendees
Writing Workshop ⟡ Women & Body Horror ⟡ Beginner-Friendly ⟡ Siya & Caroline
Central Market - North, 4001 N. Lamar Blvd., Austin, TX, USWelcome to READ—WRITE—REMIX: a reading club + creative writing workshop + social hour! We read an interesting article, poem, or story, talk about it together, and write about it for 15 minutes. We then "remix" our thoughts by discussing anything we want to share. Then we write for another 15! And after that, we just hang out and chat ☺️🫶🏼📝
In this way, we come to deepen our understanding of the text, ourselves, and each other.
Join us for a beginner-friendly writing workshop featuring works by Austin writers Caroline Costello and Siya Asatkar, as well as an excerpt from Carmen Maria Machado's short story, 'The Husband Stitch.'
All three of these works investigate what horror means in the context of the female body, so prepare for a nuanced—and slightly disturbing—discussion!
Please find our six-page reading packet linked here and read all three works in advance of our Wednesday discussion.
https://docs.google.com/document/d/1sPrZQiKjw2kFETlqOIQucLEQvKANGn07Lyov1CUoAAs/edit?usp=sharing
Highlighting Emerging Austin Writers
In line with our June-July theme of "The City," this writing workshop is part of a series built around supporting young and emerging Austin writers. This is one of the very first events presenting Siya Asatkar and Caroline Costello's literary work to the public. We hope you'll enjoy it as much as we do.
Our Theme for June & July: The City
Every 1-3 months, our group chooses a special theme to explore in our events. This writing workshop is part of our June-July session on "The City." How do we make the decision that it's worthwhile to live or leave somewhere? What does our city owe us and what do we owe it back? What does it mean to "Keep Austin Weird"? How do art and literature expand or limit our sense of civic possibilities? What new kinds of cities and city life can we imagine? And how will we know when this city has become ours?
These are some of the questions we hope to investigate this month, while offering Austinites a creative home in our own arts & humanities community.About Us
This group is a project by Difficult Friends, a community-run arts & humanities club: Website ⟡ Instagram
We empower Austinites to tackle Difficult ideas and projects.
Our core values are:- creative growth,
- intellectual challenge,
- human connection, and
- civic imagination.
Our events are designed as fun intellectual workouts and creative experiments. We host workshops and discussions that push Austin residents to think harder thoughts, make cooler stuff, and connect more deeply across their human differences.
This is not an organization for the faint of heart. As our name suggests, we take pride in being Difficult Friends and in confronting Difficult challenges.
Meaning is Difficult! Embrace the Difficult!
About Your Hosts
Caroline Costello is a speculative fiction writer in Austin. She has a professional background in editing and copywriting, but prefers writing short stories. Her work is framed by dark humor and explores religious and philosophical themes, and the absurdity of the human experience. She enjoys drinking red wine and rescuing large dogs.
Siya Asatkar was born in Austin and never left. She loves to read and hesitates to write. When she does write, she hopes for her stories to communicate the truth and beauty of a bygone era. A few of her favorite authors are Flaubert, Céline, and Baldassare Castiglione.
Statement of Welcome & Inclusivity
Here at Difficult Friends, we believe everybody can be Difficult. ;-)
Difficult Friends is an inclusive community space, and we particularly seek to protect and welcome our LGBTQIA+, queer, transgender, and nonbinary members. Event attendees may be asked to share their preferred pronouns and will be asked to respect the preferred pronouns shared by other participants. Women, immigrants, people of color, religious minorities, people with disabilities, and neurodivergent folks seeking a diverse community are also especially encouraged to attend!
Photography Policy
The event organizers of this meetup may take photos or videos of our events. By attending this event, you consent to being filmed and photographed. (If it’s Rachel, don’t worry - she will airbrush any blemishes & imperfections xoxo)!24 attendees
THE BIG QUESTIONS: Other Cities, Other Lives ⟡ Philosophical Dinner
Arpeggio Grill, 6619 Airport Blvd, Austin, TX, USWelcome to The Big Questions, a casual dinner series that explores the philosophical dilemmas that ground our ordinary lives. There's light reading assigned, but this event is very loosely structured compared to our other workshops - no guided facilitation, exercises, or assigned questions. Just read the article and come prepared to chat about it over dinner!
Our Theme for June & July: The City
Every 1-3 months, our group chooses a special theme to explore in our events. This writing workshop is part of our June-July session on "The City." How do we make the decision that it's worthwhile to live in one particular place, instead of another? What does our city owe us and what do we owe it back? What does it mean to "Keep Austin Weird"? How do art and literature expand or limit our sense of civic possibilities? What new kinds of cities and city life can we imagine? And how will we know when this city has become ours?
These are some of the questions we hope to investigate this month, while offering Austinites a creative home in our own arts & humanities community.
Other Cities, Other Lives ⟡ Assigned Reading
This week over dinner, we'll be exploring how time and space affect our attachments to loved ones, and how those in turn affect our feelings of rootedness in or disenchantment with city life.
Please read the following brief article and two poems ahead of our discussion:
https://waitbutwhy.com/2015/12/the-tail-end.html
https://docs.google.com/document/d/1BOPX5l8RZZeYy3c3e-myD8E5o_5REWXfPZ9LFTryl7s/edit?usp=sharing
Location
We'll be meeting at Arpeggio Grill, a mediterranean restaurant located at 6619 Airport Blvd. https://arpeggiogrill.com/
About Us
This group is a project by Difficult Friends, a community-run arts & humanities club: Website ⟡ Instagram
We empower Austinites to tackle Difficult ideas and projects.
Our core values are:- creative growth,
- intellectual challenge,
- human connection, and
- civic imagination.
Our events are designed as fun intellectual workouts and creative experiments. We host workshops and discussions that push Austin residents to think harder thoughts, make cooler stuff, and connect more deeply across their human differences.
This is not an organization for the faint of heart. As our name suggests, we take pride in being Difficult Friends and in confronting Difficult challenges.
Meaning is Difficult! Embrace the Difficult!
About Your Host
Trung Nguyen is a humanist, urbanist, and a member of Difficult Friends.
Statement of Welcome & Inclusivity
Here at Difficult Friends, we believe everybody can be Difficult. ;-)
Difficult Friends is an inclusive community space, and we particularly seek to protect and welcome our LGBTQIA+, queer, transgender, and nonbinary members. Event attendees may be asked to share their preferred pronouns and will be asked to respect the preferred pronouns shared by other participants. Women, immigrants, people of color, religious minorities, people with disabilities, and neurodivergent folks seeking a diverse community are also especially encouraged to attend!
That said, to quote the progressive labor activist Maurice Mitchell, we do not accept “using one’s identity or personal experience as a justification for a political position. You may hear someone argue, ‘As a working-class, first-generation American, Southern woman…I say we have to vote no.’ What’s implied is that one’s identity is a comprehensive validator of one’s political strategy—that identity is evidence of some intrinsic ideological or strategic legitimacy. Marginalized identity is deployed as a conveyor of a strategic truth that must simply be accepted. Likewise, historically privileged identities are essentialized, flattened, and frequently—for better or worse—dismissed.
To be clear, personal identity and individual experience are important. And while it is true that the ‘personal is political,’ the personal cannot trump strategy nor should it overwhelm the collective interest. Identity is too broad a container to predict one’s politics or the validity of a particular position... One’s racial or gender identity, sex, or membership in any marginalized community is, in and of itself, insufficient information to position someone in leadership or mandate that their perspective be adopted.
People with marginal identities, as human beings, suffer all the frailties, inconsistencies, and failings of any other human. Genuflecting to individuals solely based on their socialized identities or personal stories deprives them of the conditions that sharpen arguments, develop skills, and win debates. We infantilize members of historically marginalized or oppressed groups by seeking to placate or pander instead of being in a right relationship, which requires struggle, debate, disagreement, and hard work. This type of false solidarity is a form of charity that weakens the individual and the collective. Finding authentic alignment and solidarity among diverse voices is serious labor. After all, ‘steel sharpens steel.’”
For a concise summary of my views re: identitarian politics as this meetup’s lead organizer, feel free to refer to his excellent article Building Resilient Organizations.
Photography Policy
The event organizers of this meetup may take photos or videos of our events. By attending this event, you consent to being filmed and photographed. (If it’s Rachel, don’t worry - she will airbrush any blemishes & imperfections xoxo)!15 attendeesDrake X Impressionism ⟡ THE BREAKDOWN ⟡ Pop Culture X Art History ⟡ ATX Artists
Darwin's Pub, 223 E 6th St, Austin, TX, USJoin us for THE BREAKDOWN: a bar lecture series where ATX artists explain their favorite artworks, covering everything from deep dives into Renaissance sculpture to nuanced takes on the best of pop culture.
Our Inaugural Set of Topics: Soft Light & Soft Boys ⟡ Understanding The Impressionists & Drake
From June-July, the theme of our arts & humanities club is "The City," Although at first glance, painters like Claude Monet may seem to have little in common with Aubrey Graham, these artists share a deep commitment to portraying urban life and the myriad complexities of being out in the streets.
In Drake's own words:
Shakiness, man, I don't have no time for that
My city too turned up, I'll take the fine for that
This been where you find me at
That's been where you find me atCome join us to better understand the "Views" of these exceptionally influential modern artists.
Your Presenters For THE BREAKDOWN: Rachel & Sean
Sean Saldaña is a KUT News reporter who has presented his archival research and oral storytelling at venues like Bass Concert Hall, in addition to appearing regularly on Austin's public radio and formerly on NPR. A native Austinite and Texas Ex, Sean moonlights as a stand-up comic and is currently competing in Cap City Comedy Club's 'Funniest Person in Austin' Contest.
Rachel Summer Cheong holds an A.B. in the History of Art and Architecture from Harvard College. A multidisciplinary artist and cultural organizer, her work has been used by magazines like Vox and Verdict, as well as cultural institutions like the New York Philharmonic and local non-profits like Move Texas. She loves taking photos, going dancing, and organizing whimsical free events.
Event Structure
Come join us at Darwin's Pub on Tuesday, June 23 from 7-9 PM for two short lectures on The Impressionists and Drake, followed by audience Q&A and an open mixer with the presenters. Attendees will be provided with post-its on which to doodle during the talks and write down their thoughts from the event.
Audience members will also be able to vote on whose art they appreciate more: The Impressionists... or Drake?
Our Theme for June & July: The City
Every 1-3 months, our group chooses a special theme to explore in our events. This writing workshop is part of our June-July session on "The City." How do we make the decision that it's worthwhile to live or leave somewhere? What does our city owe us and what do we owe it back? What does it mean to "Keep Austin Weird"? How do art and literature expand or limit our sense of civic possibilities? What new kinds of cities and city life can we imagine? And how will we know when this city has become ours?
These are some of the questions we hope to investigate this month, while offering Austinites a creative home in our own arts & humanities community.
About Us
This group is a project by Difficult Friends, a community-run arts & humanities club: Website ⟡ Instagram
We empower Austinites to tackle Difficult ideas and projects.
Our core values are:- creative growth,
- intellectual challenge,
- human connection, and
- civic imagination.
Our events are designed as fun intellectual workouts and creative experiments. We host workshops and discussions that push Austin residents to think harder thoughts, make cooler stuff, and connect more deeply across their human differences.
This is not an organization for the faint of heart. As our name suggests, we take pride in being Difficult Friends and in confronting Difficult challenges.
Meaning is Difficult! Embrace the Difficult!
Statement of Welcome & Inclusivity
Here at Difficult Friends, we believe everybody can be Difficult. ;-)
Difficult Friends is an inclusive community space, and we particularly seek to protect and welcome our LGBTQIA+, queer, transgender, and nonbinary members. Event attendees may be asked to share their preferred pronouns and will be asked to respect the preferred pronouns shared by other participants. Women, immigrants, people of color, religious minorities, people with disabilities, and neurodivergent folks seeking a diverse community are also especially encouraged to attend!
Photography Policy
The event organizers of this meetup may take photos or videos of our events. By attending this event, you consent to being filmed and photographed. (If it’s Rachel, don’t worry - she will airbrush any blemishes & imperfections xoxo)!22 attendees
Past events
14
