CROSSTALK · FREE CONVERSATION QUESTIONS
Past the first date and into the good stuff.
Start with Warm Up and see where the conversation takes you. Ask one question, listen to the answer, and ask it back. Anyone can pass at any time. There is no rush to go deeper.
Warm Up
- What is something you are weirdly good at?
- What did you want to be at ten, and how close did you get?
- What does a perfect Sunday look like for you?
- What would your walk-up song be?
- Two truths and a lie. Go.
- What is your go-to karaoke song?
- If you could master any skill overnight, what would it be?
- What is the most spontaneous thing you have ever done?
- What is your comfort movie or show?
- What is on your bucket list that surprises people?
Get Real
- Who in your life knows you best?
- How do you know when someone cares about you?
- How do you like to be comforted on a hard day?
- What has a past relationship taught you about yourself?
- What is something you have changed your mind about in the last few years?
- Do you recharge with people or alone?
- When you are upset, do you want to talk right away or need space first?
- What small gesture means a lot to you?
- What did the relationships you grew up around teach you about love?
- What is a green flag you look for in people?
Go Deep
- What are you looking for right now: something casual, something serious, or still figuring it out?
- What is a dealbreaker you learned the hard way?
- What does a healthy argument look like to you?
- What do you want your next relationship to have that your last ones did not?
- What would make you feel secure with someone?
- What does commitment mean to you?
- How do you handle money in a relationship: split, share, or it depends?
- What do you need from a partner when life gets hard?
- What does your ideal balance of together time and alone time look like?
- How do you show up for someone you are committed to?
Found a question you want to ask someone? Send them this page.