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What's Love Got To Do With It? A Premise Deep Dating Session

This session is part of our Deep Dating series in Portland, Oregon. This is not a matchmaking experience. Instead, we bring single people together to explore the actual lived experience of being single in the modern world, where dating apps promise infinite choice while delivering exhaustion, where everyone seems to be optimizing for love like it's a career move, and where admitting you're actually okay being single can feel like either radical self acceptance or defensive denial. 


Through shared works of art, we find empathy and understanding for an experience that is often narrated by everyone except those living it.

Being single in a coupled world can feel like standing still while everyone else moves forward on some predetermined track. 


We're told singlehood is a temporary state, a waiting room before "real life" begins. Yet more people are single for longer periods than ever before, and some are choosing to remain so. This raises urgent questions about identity, completeness, and what we're actually seeking when we think we're looking for love.


The single experience is often narrated by others: pitied relatives, well meaning friends, a culture obsessed with romantic completion. But what happens when we examine singlehood from the inside? When we stop treating it as a problem to be solved and start asking what it reveals about our assumptions of happiness, identity, and belonging?


Our conversation will explore:

  • What does the single experience teach us about who we are when we're not defined through partnership?

  • How much of our search for love is actually a search for something else entirely?

  • What stories do we tell ourselves about being single, and whose stories are they?

  • What would change if we saw singlehood as a complete state rather than a lacking one?

What's Love Got To Do With It? A Premise Deep Dating Session

This session is part of our Deep Dating series in Portland, Oregon. This is not a matchmaking experience. Instead, we bring single people together to explore the actual lived experience of being single in the modern world, where dating apps promise infinite choice while delivering exhaustion, where everyone seems to be optimizing for love like it's a career move, and where admitting you're actually okay being single can feel like either radical self acceptance or defensive denial. 


Through shared works of art, we find empathy and understanding for an experience that is often narrated by everyone except those living it.

Being single in a coupled world can feel like standing still while everyone else moves forward on some predetermined track. 


We're told singlehood is a temporary state, a waiting room before "real life" begins. Yet more people are single for longer periods than ever before, and some are choosing to remain so. This raises urgent questions about identity, completeness, and what we're actually seeking when we think we're looking for love.


The single experience is often narrated by others: pitied relatives, well meaning friends, a culture obsessed with romantic completion. But what happens when we examine singlehood from the inside? When we stop treating it as a problem to be solved and start asking what it reveals about our assumptions of happiness, identity, and belonging?


Our conversation will explore:

  • What does the single experience teach us about who we are when we're not defined through partnership?

  • How much of our search for love is actually a search for something else entirely?

  • What stories do we tell ourselves about being single, and whose stories are they?

  • What would change if we saw singlehood as a complete state rather than a lacking one?

Express Interest

This session is part of our Deep Dating series in Portland, Oregon. This is not a matchmaking experience. Instead, we bring single people together to explore the actual lived experience of being single in the modern world, where dating apps promise infinite choice while delivering exhaustion, where everyone seems to be optimizing for love like it's a career move, and where admitting you're actually okay being single can feel like either radical self acceptance or defensive denial. 


Through shared works of art, we find empathy and understanding for an experience that is often narrated by everyone except those living it.

Being single in a coupled world can feel like standing still while everyone else moves forward on some predetermined track. 


We're told singlehood is a temporary state, a waiting room before "real life" begins. Yet more people are single for longer periods than ever before, and some are choosing to remain so. This raises urgent questions about identity, completeness, and what we're actually seeking when we think we're looking for love.


The single experience is often narrated by others: pitied relatives, well meaning friends, a culture obsessed with romantic completion. But what happens when we examine singlehood from the inside? When we stop treating it as a problem to be solved and start asking what it reveals about our assumptions of happiness, identity, and belonging?


Our conversation will explore:

  • What does the single experience teach us about who we are when we're not defined through partnership?

  • How much of our search for love is actually a search for something else entirely?

  • What stories do we tell ourselves about being single, and whose stories are they?

  • What would change if we saw singlehood as a complete state rather than a lacking one?

Conversation Catalysts

At Premise, a Conversation Catalyst is a short story, essay, film, or poem that sparks reflection and connection. It’s the shared reference point that grounds each session and opens the door to meaningful and deep conversation.

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  • "Why You Will Marry the Wrong Person" by Alain de Botton

    New York Times Essay

  • "The Darling" by Anton Chekhov, Short Story

  • "The Unhappiness of Being a Single Man" by Franz Kafka

    Short Prose Piece

  • "Happy Endings" by Margaret Atwood, Metafictional Story

  • "What No One Ever Told You About People Who Are Single" by Bella DePaulo, TED Talk

Preparation: < 1.5 hours

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We examine how philosophy, fiction, and social science reveal the complex truth about single life and our assumptions about what love is supposed to solve.

"Why You Will Marry the Wrong Person" by Alain de Botton New York Times Essay (15 minute read)

De Botton argues that our romantic ideals doom us to disappointment, suggesting we seek impossible perfection rather than "good enough" compatibility. He proposes that the right person is simply "a good teammate for the project of being alive." This reframing asks us to examine what we think love will solve and why we believe another person holds the key to our completion. De Botton's philosophy challenges us to ask: What fantasies do we project onto romantic love? How does the fear of being single drive us toward unsuitable partnerships? What if accepting imperfection in ourselves and others is the starting point, not the compromise?

Ideas for readings or films?

We’d love to hear your suggestions for stories, essays, films, or poems that could spark rich conversation at Premise. Our texts are short (under 3 hours to prepare), substantive enough for deep discussion, and accessible to a wide audience.

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  • "Why You Will Marry the Wrong Person" by Alain de Botton

    New York Times Essay

  • "The Darling" by Anton Chekhov, Short Story

  • "The Unhappiness of Being a Single Man" by Franz Kafka

    Short Prose Piece

  • "Happy Endings" by Margaret Atwood, Metafictional Story

  • "What No One Ever Told You About People Who Are Single" by Bella DePaulo, TED Talk

Preparation: < 1.5 hours

We examine how philosophy, fiction, and social science reveal the complex truth about single life and our assumptions about what love is supposed to solve.

"Why You Will Marry the Wrong Person" by Alain de Botton New York Times Essay (15 minute read)

De Botton argues that our romantic ideals doom us to disappointment, suggesting we seek impossible perfection rather than "good enough" compatibility. He proposes that the right person is simply "a good teammate for the project of being alive." This reframing asks us to examine what we think love will solve and why we believe another person holds the key to our completion. De Botton's philosophy challenges us to ask: What fantasies do we project onto romantic love? How does the fear of being single drive us toward unsuitable partnerships? What if accepting imperfection in ourselves and others is the starting point, not the compromise?

Conversation Catalysts

At Premise, a Conversation Catalyst is a short story, essay, film, or poem that sparks reflection and connection. It’s the shared reference point that grounds each session and opens the door to meaningful and deep conversation.

  • "Why You Will Marry the Wrong Person" by Alain de Botton

    New York Times Essay

  • "The Darling" by Anton Chekhov, Short Story

  • "The Unhappiness of Being a Single Man" by Franz Kafka

    Short Prose Piece

  • "Happy Endings" by Margaret Atwood, Metafictional Story

  • "What No One Ever Told You About People Who Are Single" by Bella DePaulo, TED Talk

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Text Set A

Preparation: < 1.5 hours

Session Description

We examine how philosophy, fiction, and social science reveal the complex truth about single life and our assumptions about what love is supposed to solve.

"Why You Will Marry the Wrong Person" by Alain de Botton New York Times Essay (15 minute read)

De Botton argues that our romantic ideals doom us to disappointment, suggesting we seek impossible perfection rather than "good enough" compatibility. He proposes that the right person is simply "a good teammate for the project of being alive." This reframing asks us to examine what we think love will solve and why we believe another person holds the key to our completion. De Botton's philosophy challenges us to ask: What fantasies do we project onto romantic love? How does the fear of being single drive us toward unsuitable partnerships? What if accepting imperfection in ourselves and others is the starting point, not the compromise?

"The Darling" by Anton Chekhov Short Story (45 minute read)

Olenka, "The Darling," completely transforms herself based on whoever she loves, adopting their opinions, interests, and worries as her own. When alone, she becomes empty, unable to form a single opinion about the weather. Chekhov presents this with both comedy and tragedy, forcing us to ask whether Olenka is pitiable or whether she simply makes visible what we all do more subtly. The story raises essential questions: Who are we when no one is watching? How much of identity is actually performed for or through others? Is the fear of being single really a fear of meeting ourselves without mediation?

"The Unhappiness of Being a Single Man" by Franz Kafka Short Prose Piece (5 minute read)

Kafka's brief, aching meditation imagines coming home alone night after night, building to a crescendo of isolation. Yet the piece also reveals how the single person becomes a projection screen for others' fears about loneliness and incompleteness. Kafka forces us to consider: Is the pain of singlehood inherent or socially constructed? How do we separate actual loneliness from the story we're told about being alone? What's the difference between solitude and isolation?

"Happy Endings" by Margaret Atwood Metafictional Story (10 minute read)

Atwood provides multiple versions of the same romance, all ending in death, cheekily noting that "John and Mary die. John and Mary die. John and Mary die." By showing that all stories have the same ending, she exposes our obsession with middles, with the "how and why" rather than the inevitable what. The story suggests that our focus on achieving the "happy ending" of coupling might be missing the point entirely. Atwood asks us to consider: What narrative are we trying to complete by coupling? Why do we treat finding love as an ending rather than a beginning? What would happen if we focused on the quality of the middle, the living, rather than achieving particular plot points?

"What No One Ever Told You About People Who Are Single" by Bella DePaulo TED Talk (15 minutes)

DePaulo, who coined the term "singlism," dismantles the myths about single people being lonely, selfish, and immature. Her research shows single people are often more connected to communities, maintain stronger friendships, and contribute more to civic life. She argues that "matrimania," our cultural obsession with marriage, blinds us to the richness of single life. DePaulo's research poses vital questions: What if everything we "know" about single unhappiness is wrong? How does matrimania shape even single people's view of themselves? What would society look like if we valued friendship and community connection as much as romantic partnership?

Text Set A

Preparation: < 1.5 hours

Session Description

We examine how philosophy, fiction, and social science reveal the complex truth about single life and our assumptions about what love is supposed to solve.

"Why You Will Marry the Wrong Person" by Alain de Botton New York Times Essay (15 minute read)

De Botton argues that our romantic ideals doom us to disappointment, suggesting we seek impossible perfection rather than "good enough" compatibility. He proposes that the right person is simply "a good teammate for the project of being alive." This reframing asks us to examine what we think love will solve and why we believe another person holds the key to our completion. De Botton's philosophy challenges us to ask: What fantasies do we project onto romantic love? How does the fear of being single drive us toward unsuitable partnerships? What if accepting imperfection in ourselves and others is the starting point, not the compromise?

"The Darling" by Anton Chekhov Short Story (45 minute read)

Olenka, "The Darling," completely transforms herself based on whoever she loves, adopting their opinions, interests, and worries as her own. When alone, she becomes empty, unable to form a single opinion about the weather. Chekhov presents this with both comedy and tragedy, forcing us to ask whether Olenka is pitiable or whether she simply makes visible what we all do more subtly. The story raises essential questions: Who are we when no one is watching? How much of identity is actually performed for or through others? Is the fear of being single really a fear of meeting ourselves without mediation?

"The Unhappiness of Being a Single Man" by Franz Kafka Short Prose Piece (5 minute read)

Kafka's brief, aching meditation imagines coming home alone night after night, building to a crescendo of isolation. Yet the piece also reveals how the single person becomes a projection screen for others' fears about loneliness and incompleteness. Kafka forces us to consider: Is the pain of singlehood inherent or socially constructed? How do we separate actual loneliness from the story we're told about being alone? What's the difference between solitude and isolation?

"Happy Endings" by Margaret Atwood Metafictional Story (10 minute read)

Atwood provides multiple versions of the same romance, all ending in death, cheekily noting that "John and Mary die. John and Mary die. John and Mary die." By showing that all stories have the same ending, she exposes our obsession with middles, with the "how and why" rather than the inevitable what. The story suggests that our focus on achieving the "happy ending" of coupling might be missing the point entirely. Atwood asks us to consider: What narrative are we trying to complete by coupling? Why do we treat finding love as an ending rather than a beginning? What would happen if we focused on the quality of the middle, the living, rather than achieving particular plot points?

"What No One Ever Told You About People Who Are Single" by Bella DePaulo TED Talk (15 minutes)

DePaulo, who coined the term "singlism," dismantles the myths about single people being lonely, selfish, and immature. Her research shows single people are often more connected to communities, maintain stronger friendships, and contribute more to civic life. She argues that "matrimania," our cultural obsession with marriage, blinds us to the richness of single life. DePaulo's research poses vital questions: What if everything we "know" about single unhappiness is wrong? How does matrimania shape even single people's view of themselves? What would society look like if we valued friendship and community connection as much as romantic partnership?

Conversation Catalysts

At Premise, a Conversation Catalyst is a short story, essay, film, or poem that sparks reflection and connection. It’s the shared reference point that grounds each session and opens the door to meaningful and deep conversation.

5.png

Text Set B

Preparation: < 1.5 hours

Session Description

Text Set A

Preparation: < 1.5 hours

Session Description

We examine how philosophy, fiction, and social science reveal the complex truth about single life and our assumptions about what love is supposed to solve.

"Why You Will Marry the Wrong Person" by Alain de Botton New York Times Essay (15 minute read)

De Botton argues that our romantic ideals doom us to disappointment, suggesting we seek impossible perfection rather than "good enough" compatibility. He proposes that the right person is simply "a good teammate for the project of being alive." This reframing asks us to examine what we think love will solve and why we believe another person holds the key to our completion. De Botton's philosophy challenges us to ask: What fantasies do we project onto romantic love? How does the fear of being single drive us toward unsuitable partnerships? What if accepting imperfection in ourselves and others is the starting point, not the compromise?

"The Darling" by Anton Chekhov Short Story (45 minute read)

Olenka, "The Darling," completely transforms herself based on whoever she loves, adopting their opinions, interests, and worries as her own. When alone, she becomes empty, unable to form a single opinion about the weather. Chekhov presents this with both comedy and tragedy, forcing us to ask whether Olenka is pitiable or whether she simply makes visible what we all do more subtly. The story raises essential questions: Who are we when no one is watching? How much of identity is actually performed for or through others? Is the fear of being single really a fear of meeting ourselves without mediation?

"The Unhappiness of Being a Single Man" by Franz Kafka Short Prose Piece (5 minute read)

Kafka's brief, aching meditation imagines coming home alone night after night, building to a crescendo of isolation. Yet the piece also reveals how the single person becomes a projection screen for others' fears about loneliness and incompleteness. Kafka forces us to consider: Is the pain of singlehood inherent or socially constructed? How do we separate actual loneliness from the story we're told about being alone? What's the difference between solitude and isolation?

"Happy Endings" by Margaret Atwood Metafictional Story (10 minute read)

Atwood provides multiple versions of the same romance, all ending in death, cheekily noting that "John and Mary die. John and Mary die. John and Mary die." By showing that all stories have the same ending, she exposes our obsession with middles, with the "how and why" rather than the inevitable what. The story suggests that our focus on achieving the "happy ending" of coupling might be missing the point entirely. Atwood asks us to consider: What narrative are we trying to complete by coupling? Why do we treat finding love as an ending rather than a beginning? What would happen if we focused on the quality of the middle, the living, rather than achieving particular plot points?

"What No One Ever Told You About People Who Are Single" by Bella DePaulo TED Talk (15 minutes)

DePaulo, who coined the term "singlism," dismantles the myths about single people being lonely, selfish, and immature. Her research shows single people are often more connected to communities, maintain stronger friendships, and contribute more to civic life. She argues that "matrimania," our cultural obsession with marriage, blinds us to the richness of single life. DePaulo's research poses vital questions: What if everything we "know" about single unhappiness is wrong? How does matrimania shape even single people's view of themselves? What would society look like if we valued friendship and community connection as much as romantic partnership?

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