Conversation Starters: Would You Rather

The “Would You Rather” Prompt

“Would you rather have pizza for every meal or never eat pizza again?” “Would you rather fly or be invisible?”

These classic “Would You Rather” prompts pose fun dilemmas that spark conversation, laughter, and debate. In educational settings, especially tutoring environments, these prompts can go far beyond small talk—they can be powerful tools for developing students’ communication, listening, and critical thinking skills.

In this type of activity, students are asked to choose between two options, often both appealing or both unappealing, and explain their reasoning. The question format may be playful or tied to content—like math! The beauty lies in the process: students must make a choice, explain their reasoning, and listen actively to others.

“Would You Rather” fosters mathematical thinking by encouraging students to make comparisons, estimate, justify, and defend their choices—all foundational skills in problem-solving. It shifts the focus from “What’s the answer?” to “What do you think—and why?”

Voice Matters in Math: Fostering SEL Competencies Through “Would You Rather”

“Would You Rather” nurtures a safe space for students to express themselves, reflect, and build confidence. The activity aligns naturally with key Social and Emotional Learning (SEL) competencies like:

Self-awareness

Students reflect on their own preferences and decision-making processes.

Social awareness and relationship skills

Students practice listening respectfully and understanding others’ viewpoints.

Responsible decision-making

Students learn to weigh options and communicate the reasoning behind their choices.

In math, where students may feel pressure to “get it right,” the “Would You Rather” activity flips the script: there’s no single correct answer. Every student has a voice. Every explanation matters.

Would You Rather: Math as a Subject vs. Math as an Experience

Focus on Understanding, Not Just Memorizing

Traditional math instruction often emphasizes memorization and right answers. But “Would You Rather” fosters mathematical thinking by encouraging students to make comparisons, estimate, justify, and defend their choices—all foundational skills in problem-solving. It shifts the focus from “What’s the answer?” to “What do you think—and why?”

Real-World Applications

Dilemma-based prompts can connect math to real life. For example:

“Would you rather buy a $15 movie ticket with a $10 snack combo, or a $20 unlimited viewing pass with one free snack per visit?”

This kind of prompt gets students thinking about budgeting, value, and trade-offs—essential life math skills with real-world relevance.

Collaboration and Communication

As students share and discuss their answers, they develop skills essential for group work and collaboration—skills that extend far beyond the math classroom. According to The Math Project, discussing math helps build time management, organization, and communication skills. These are life-long assets, not just classroom goals.

Math as a Tool

When students engage in playful, low-stakes math talk through tasks like “Would You Rather,” they begin to see math as a tool for decision-making, reasoning, and connection—not just as numbers on a page.

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Math as a Community

When everyone participates, even quietly with a show of hands, students begin to see math as a shared experience. “Would You Rather” builds community by validating all voices and showing that every perspective has value.

How to Facilitate “Would You Rather”

  1. Tutor presents a question and a visual prompt.
    1. Students view two options side-by-side, such as a graph, image, or brief description.
  2. Tutor gives students time to think or write responses.
    1. Students consider both choices and reflect on their reasoning.
  3. Tutor invites students to share and elaborate.
    1. Students take turns explaining their answers, with the option to pass if they prefer not to speak.
  4. Tutor shares their own answer and models reasoning.
    1. Students connect the tutor’s thinking to their own ideas and feel affirmed through thoughtful reflection and inclusive discussion.

Validate student responses by making connections to your own thinking or highlighting interesting reasoning.

Tips for Using “Would You Rather” Effectively

  • Use visuals to lower barriers and help students visualize the choices.
  • Tailor questions to your students’ interests and cultural context.
  • Avoid overly personal or sensitive topics. Keep the environment inclusive.
  • Use hand signals (e.g., hold up one or two fingers) for students who prefer not to speak aloud.

Whether you’re aiming to build SEL skills, encourage discussion, or make math more engaging, “Would You Rather” is a simple yet powerful opening activity. It helps students find their voice, listen with curiosity, and develop the critical thinking skills that translate seamlessly to solving problems—both in math and in life.

Social-Emotional Learning Reflection Prompts

"Choose One" Conversation Starter

Stay tuned for more activities and techniques in our “Conversation Starters” series to enhance your high-impact tutoring sessions. 

Integrate “Would You Rather” and other conversation starters to your math curriculum.