How to Host in 2025
Wisdom from Leah Libresco Sargeant
I find hosting confusing.
Are we supposed to do “scruffy hospitality”—inviting people into our homes and lives “as is” rather than all tidied up, offering spaghetti and meatballs on paper plates rather than an elaborate hors d'oeuvres spread? Or is brunch hell and a true dinner party the only acceptable way of having guests over?
If everyone’s so lonely, why does it take so much effort to get anyone to commit and show up for something? Is there any way to avoid the epidemic of last-minute flaking? How can hosting be less exhausting and more sustainable?
To help answer all these questions and more, I reached out to a seasoned host.
“wrote the book” on intentional community. Her 2018 Building the Benedict Option is a practical complement to ’s The Benedict Option. If Dreher was arguing why we need thick, Christian community, Sargeant was telling you how to do it.So I met her at a local coffee shop to pick her brain on hosting and friendship. Her background in philosophical debate (that is, arguing in defense of things she actually believes), theater, and tech start-ups led to unusual, fresh takes on common hosting gripes.
Whether you dream of throwing a party yourself or are merely saddened by the friendship recession, I think you’ll find her advice helpful, optimistic, and entertaining.
And if you want to read more of her work, you can subscribe below.
The Expected Value of a Party
Sargeant worked in two tech start-ups and that start-up mentality comes through in her philosophy of hosting. I asked her why she prefers niche events (she recently hosted a reading of a Dorothy Sayers play) to something more typical like cocktail parties.
She analogized it to her (“nonstandard”) approach to dating:
People prioritize too much, “I want to minimize the downside risk of this encounter” and not maximize the upside risk of it. I think a lot of people go on dates or have conversations at a party with the goal of, “I want to be pleasant. I want this to be nonbothersome for us. I don’t want to get into a conflict.”
And I think for both dates and parties, your goal should be more like, “Wow, I don’t want to miss the best part of this interaction or to learn whether we want to be friends.”
This is a social application of the investment concept of Expected Value (EV). Basically, EV considers the probability of an event along with its upside potential. For a venture capitalist, a 10% chance at a billion dollars is worth more than a 90% chance at a thousand dollars. They build their portfolios expecting a small subset will break through and yield the bulk of their returns.
Likewise, Sargeant didn’t go on a date merely hoping to have a second date. She wanted to increase her chances of finding a husband. Likewise, her parties—from initial concept to execution—aim to increase the chance that this is someone’s favorite event rather than decrease the risk that someone hates it.
She contrasts one of her events with a cocktail party, which is broadly palatable but a little bland. At a cocktail party, “goldfish” conversations reset every fifteen minutes. There are constant introductions and interruptions, but often people are more interested in keeping it light and avoiding awkwardness.
At these sorts of events, she often comes away from an interaction with no opinion of someone. To her, that’s a missed opportunity. It irritates her. She will be driving home and complain to her husband:
Leah: What is anyone doing? I have no sense of what we’re working on! What is our project at this party?
Husband: I don’t think everyone comes to a party with a project, Leah.
Leah: Well then why did they go!
She finds “What do you do?” a boring, dead-end question. She’d rather ask, “What’s something interesting that you’ve read recently,” or better yet, at something focused like her Sayers event: “Tell me where you first came across Dorothy Sayers.”
These sorts of questions are meant to forge meaningful, unanticipated connections between guests, connections Sargeant herself may not be aware of when she gets the group together.
She acknowledges that for some, the energy of a cocktail party is delightful, and a play reading sounds dreadful. Her solution is not for everyone to mimic her. In her perfect world, everyone would be throwing the events they were excited about and many different flowers would bloom.
She imagined a friend might well say, “I hate Leah’s events! I love Ben’s events! When I’m with Ben, I do feel like he sees me and he knows me, but he’s not such an aggro person about it!” And that would be totally fine with her.
I’d love to hear your thoughts on hosting and what’s worked for you!
Watching All the Snakes, Curving All the Flakes
Of course, there’s a couple issues with this seemingly simple solution. For one, to continue the investor analogy, an event that 10% of your friends would LOVE might require a fair amount of rejection at first as you build out your party roster.
And genuinely stepping out is hard.
Social media and the internet are powerful social conformity engines that push us toward least-common-denominator appeals. As Alex Murell documented, from Airbnb to coffee shops to Instagram face, there is a pressure for maximally efficient, minimally offensive design. These things are “unfamiliar but completely recognizable.”
Thus, your Disney Adults party might be a highlight of the year for a few of your friends, but it may sting to get a string of no-replies. There is a safety in low-stakes, typical events. Nevertheless, Sargeant’s life shows what can happen once your hosting moves out of the start-up phase and into the incumbent phase.
After years of events, when she wants to put on a Dorothy Sayers’ reading, she already knows which of her friends might be interested in that sort of thing. With just a few emails, her guest list is filled out, and she can invite a few new acquaintances as well. It may take time for you to build the community that shares your interests and are reliable guests, but it’s not impossible.
To that point, Sargeant urges making hosting fun and sustainable for the host. That way, you enjoy the whole process, not just the distant, abstract reward of “community.” For her, that might mean paper plates or events in the afternoon (so she doesn’t need to make dinner). She is not a tryhard, but she is a planner. She wants maximum output for minimal effort, a highly leveraged approach.
She said that last part with gusto: “Favorable conditions never come!”
One more point on the start-up analogy: Sargeant has major “founder energy.” When I interviewed Nick Gray, the author of The 2 Hour Cocktail Party, like Sargeant, he had a background in theater and start-ups. For a host, it’s undeniable that a willingness to be loud and the center of attention is a boon.
Sargeant believes hosting is far more accessible than most people think and that they are intimidated by the idea of hosting more than the thing itself, but her effervescence certainly gives her an edge. In my observation, the people who are most enthusiastic about hosting and encourage others to do it are also those who are temperamentally inclined toward stereotypical hosting energy.
You certainly can be a more reserved host, just like you can be an unorthodox founder. But it’s easier if you fit the mold, and I don’t want to downplay what Sargeant has going for her.
You Can Just Do Things
Sargeant is a theater fan, and she quoted Stephen Sondheim’s “Being Alive” in Building the Benedict Option:
Somebody need me too much.
Somebody know me too well.
Somebody pull me up short,
And put me through hell,
And give me support
For being alive.
I asked her to elaborate on this idea that things, like hosting or romance, that seem more difficult nowadays might also be the very same things that make you feel “alive.” She told me she’s since found an even better quote for how she faces the headwinds of modern life. This one’s from C.S. Lewis:
If we let ourselves, we shall always be waiting for some distraction or other to end before we can really get down to our work. The only people who achieve much are those who want knowledge so badly that they seek it while the conditions are still unfavorable. Favorable conditions never come.
She said that last part with gusto: “Favorable conditions never come!” It has become a motto in her house for making it work, even with kids and commitments and all the usual excuses. Despite 3 young ones, she read 82 books last year.
When I asked her how she does it, she explained that she sometimes reads her Kindle while holding a baby and cooking (because that way you can read one-handed). No waiting for favorable conditions in her house!
She extended this analogy of wanting knowledge to wanting community, marriage, or kids. The only people who achieve it are those who don’t make excuses, but many young people are well-practiced in blame-shifting. They have entry-level jobs in large systems where they spend all day proving how if things don’t work, it wasn’t their fault.
By contrast, when Sargeant worked on costume crew in college, she knew if she didn’t sew seams on time, the actress goes out naked and everyone knows it. It doesn’t matter if the bobbins were stolen. There would be no, “Oh, you’re right! The bobbins were stolen. There was nothing you could do.” They’d be yelling at her for not figuring it out beforehand!
As the saying goes, “The show must go on,” and if your job doesn’t inculcate the virtue of responsibility, perhaps hosting in your free time would.
Whatever your culprit is for the breakdown of community—phones, social media, housing regulations—you will die lonely if you wait for those structural problems to be solved before you get down to the work of making and maintaining friendships.
Moreover, if you wait until your kids are a certain age or you own your house or whatever arbitrary benchmark you set, you’ll miss out on the sustaining community that you need through all those life stages.
On top of that, as Sargeant writes in her book, Christians believe in a God who orders all things. We have experienced the synchronicities of passing remarks from friends guiding our steps or answering our prayers. We can host things without absolute control over their future or their impact and just offer it up to God in good faith, trusting that He can use and multiply it.
Theater types can seem so irrepressibly confident, I kept probing to see if she ever feels rejected, ever disappointed that her efforts aren’t reciprocated. She immediately answered no. And she elaborated that if you ask someone what’s going on or how you can pray for them, you’ll find any cancellation or lack of reciprocity is almost never personal.
Instead, there’s something real and difficult going on in their lives. She doesn’t want to be a stingy host keeping score of who has invited her back or cancelled the last few times. She wants to be a friend who already knows who is sick, how long they’ve been ill, and all the other things that she should be praying for.
Some people may be net-receivers for a long time, even their whole lives, and that’s okay with her too. As a parent of young kids, she knows what it’s like to receive care from others that you will be unable to reciprocate or pay forward for a long, long time.
Her next book, The Dignity of Dependence, addresses this exact subject and comes out this fall. She wants to create community that is interdependent, intergenerational, and inclusive of infants and the elderly. I find this entirely admirable, though I imagine she would concede that this need not be everyone’s hosting mission.
In your life, maybe you should start a woodworking club, amateur “Chopped” night, or Dance Dance Revolution tournament. Maybe a cocktail party is your ideal format. Maybe you should just throw yourself into a church community. Only you know what niche you can fill.
But you can be certain that favorable conditions will never come and that the world won’t magically become more sociable through sitting around and complaining. So why not take a chance on hosting, reaching out, being alive?
After all, nothing ventured, nothing gained.
I love this SO MUCH. I'm reminded of a great book I read a few years ago called The Art of Gathering. (And now I'm off to order Leah's book.)
I live in a small town where there's not a lot of interesting things going on. There are interesting people though (some, lol), and my husband and I decided that we'll need to have more parties if we are to be able to stand staying here. I love hosting, and I'm a good host. But I'm always tempted to do just what you wrote (and what The Art of Gathering talks about too) and just sort of make sure it all "goes well," instead of being more intense and intentional about what (and who) the party is for.
All to say, I'm inspired. Thanks!
Instead of "project" I go by this line from Father Brown: "Like a true philosopher, Flambeau had no aim in his holiday; but, like a true philosopher, he had an excuse. He had a sort of half purpose, which he took just so seriously that its success would crown the holiday, but just so lightly that its failure would not spoil it."