Everyday Connection
What’s something small that made you smile recently?
Who in your life do you wish you talked to more often?
What does feeling “seen” look like for you in daily life?
When was the last time someone surprised you with kindness?
How do you usually show people you care about them?
What’s a moment from today or this week you’d like to keep?
Is there a little habit or ritual that helps you feel grounded?
What’s something most people don’t know you appreciate?
Who’s someone that always brings you back to yourself?
What’s a phrase or gesture that always feels warm to receive?
What do you wish people asked you more often?
When do you feel most connected to others during your day?
Dating & Romance
What’s something small someone once did that turned you on?
How do you usually flirt — bold moves or subtle signals?
What kind of moments make you feel most desired?
What’s your love language… or your flirting language?
What kind of date makes you think, “I want more of this”?
What’s a romantic scene or gesture that stuck with you?
What does “emotional chemistry” feel like in your body?
When do you feel sexiest? (And what helps get you there?)
What’s a turn-on that’s more about connection than touch?
If someone really saw the soft side of you, what would they notice?
What helps you go from “this is fun” to “this could be something”?
What’s one thing you’re craving more of in your romantic life?
Play & Imagination
If your inner child had the mic right now, what would they shout?
What would your dream treehouse or secret hideout include?
If you had to wear one outfit for an imaginary adventure, what would it be?
What game, toy, or activity made you lose track of time as a kid?
If you could magically master any playful skillwhat would you pick?
What would your alter ego’s name be, and what’s their vibe?
If your life were a fantasy story what role would you play?
What's a rule you’d love to break in a totally harmless, fun way?
If we had to make up a silly ritual right now, what would it be?
What’s the most imaginative compliment you could give someone right now?
If you had a magic remote that paused the world, what’s the first thing you’d do?
What’s something totally weird or playful you secretly wish more adults did?
Family Roots
What’s a tradition or ritual from your family that you secretly love?
What’s a food that brings you back to your childhood?
What’s one lesson someone in your family taught you that stuck?
How are you similar to someone in your family in a way that surprises you?
What’s something about your background or upbringing you feel proud of?
What stories or values do you hope continue in the next generation?
What’s a family story that gets told over and over, and why do you think it lives on?
What’s something you’ve learned to do differently from how you were raised?
What role did you tend to play in your family growing up?
Is there a family mystery, legend, or inside joke that still lives on?
What’s something you wish you could ask an ancestor, if you had the chance?
Groups & Icebreakers
What’s a fun fact about you that most people don’t expect?
What’s your go-to karaoke or car singalong song?
If you could instantly become great at one random thing, what would it be?
What’s the weirdest or most unexpected job you’ve ever had?
What’s something you’ve tried once and would totally do again?
If your mood right now were a weather report, what would it say?
What’s a smell that instantly makes you feel at home?
If you had to swap lives with a cartoon character for a day, who would you pick?
What’s one small joy that never gets old?
If you had to give your current vibe a movie title, what would it be?
What’s something simple that always makes you laugh?
What’s a made-up holiday you think the world really needs?
Family Roots
What’s something you’ve healed from that shaped who you are today?
How do you know when someone truly understands you?
What kind of love or care feels hardest for you to receive, and why?
What’s something you’ve never said out loud but think about often?
When do you feel most safe being fully vulnerable?
What’s a part of you that’s still becoming, and what support helps it grow?
How do you handle distance or disconnection in relationships you care about?
What do you want more of in your emotional or intimate life right now?
What’s one experience from your past that you wish someone had witnessed with you?
How do you tend to show love when words don’t feel like enough?
What would deepen trust between us even more?
What’s a hope you hold close that feels a little scary to share?
Life Stories
What’s a moment in your life that changed how you see the world?
What’s a risk you took that you’re glad you didn’t skip?
Who believed in you at a time when you really needed it?
What’s a childhood memory that still feels vivid today?
What’s a place that holds a piece of your story, and why?
What chapter of your life taught you the most about resilience?
When was a time you surprised yourself — in a good way?
What’s something you used to believe that you’ve since outgrown?
What’s one decision you look back on as a turning point?
Who has had the biggest influence on the person you are now?
What’s a story from your life you don’t tell often, but wish more people knew?
If your life were a book, what would this current chapter be called?
Grief & Tender Times
Who or what do you still carry with you?
What helped you feel less alone during a hard time?
What do you wish people understood better about grief?
When you're tender, what kind of comfort works for you?
What does healing feel like for you right now?
Was there any beauty that surprised you during loss?
How do you honor someone or something you’ve lost?
Is there a song, phrase, or item that brings you peace?
What does it mean to be held when you're hurting?
Who shows up for you, and how do they do it?
What have you learned about yourself through grief?
Celebrations & Milestones
What’s something you’re proud of that deserves a little celebration?
What personal win have you quietly carried?
What moment recently made you feel truly alive?
Who showed up for you when it really counted?
What milestone did you reach that felt especially meaningful?
What’s something you’ve done that younger you would cheer for?
What do you want to pause and appreciate before moving forward?
What’s a joyful memory you love to replay in your mind?
What small step ended up making a big difference?
Who do you wish you could celebrate something with right now?
What does celebration look like for you — loud or quiet?
What’s something worth toasting to, right here, right now?