About Us
At Questions to Ask Me, we believe the best conversations aren’t built on perfect answers—they start with thoughtful questions. Not to quiz or impress, but to connect.
Whether it’s a quick exchange that warms up the first five minutes of meeting someone new, or the kind of late-night talk that lingers in your memory, questions have a quiet power. They spark laughter, build trust, and open doors to understanding—both of others and of ourselves.
We’re here to make that power accessible to anyone, anywhere. You won’t find recycled lists or stale icebreakers. Instead, we offer prompts that are designed to live beyond the screen—rooted in psychology, shaped by storytelling, and infused with emotional intelligence.
Every question we share is made for real conversations in real moments, helping you go beyond small talk into something that feels authentic and alive.
Better Questions, Brighter Conversations.
Questions to Ask Me is your go-to source for conversation-ready prompts that feel natural, thoughtful, and meaningful. Each one is designed to spark curiosity, reflection, and real talk.
What You’ll Find Here
We don’t just create prompts. We create opportunities—for insight, reflection, connection, and belonging. Our questions fall into three main categories:
Icebreakers & Fun Questions
Playful, lighthearted, and designed to dissolve awkwardness without forcing anything. From clever “would-you-rather” prompts to creative “what-if” scenarios, these are perfect for game nights, new friendships, team events, road trips, or simply filling those small silences with something memorable.
Deep & Meaningful Questions
Gentle, intentional prompts that invite openness without pressure. They’re perfect for late-night chats, reflective journaling, therapy sessions, or anytime you want to move past surface-level small talk and toward deeper understanding.
Relationships & Self-Discovery
Prompts designed to help you explore love, identity, values, and personal growth. Whether you’re strengthening a relationship, navigating change, or getting to know yourself on a new level, these questions create space for clarity and connection.
Meet the Team
Callister Reef
Editor-in-Chief & Founder
Callister started Questions to Ask Me after a friend confessed, “I never know what to say anymore.” A former columnist and conversation designer, Callister has spent 12+ years crafting content that makes people feel seen, heard, and curious again.
Charlie Turcotte
Relationships & Self-Discovery Editor
A certified relationship educator and longtime workshop facilitator, Charlie has spent over a decade helping people explore their emotional world. Her work is informed by attachment theory, communication science, and lived experience. She brings warmth, clarity, and quiet wisdom to every question she crafts.
Amber Henry
Lifestyle Researcher
Amber blends a background in psychology and education to create questions that feel intuitive and human. She’s worked on learning platforms and wellness apps, always driven by one question: how do we get people to open up without shutting down?
Wesley Chen
Social Flow Contributor
Wesley is a communication coach with a background in performance improv and community building. He’s spent years teaching teams, friends, and total strangers how to connect faster—without the small talk trap.
Why We’re Here
We live in a world full of noise. But here, we’re carving out space for signal—for real human connection. A good question doesn’t need to be deep or brilliant. It just needs to be true to the moment.
Whether you’re meeting someone new, reconnecting with someone familiar, or sitting quietly with yourself—we hope our questions help you say something that matters.