You don’t have to go on a spendy vacation or all-out on date night to reconnect with your partner (although those things are great and you should consider this permission to do that if it works for you!). All you really need is intentional quality time, which can also look like a phones-down dinner at home, a walk outside together, or a relationship check-in where you chat about your dynamic, what’s working, and what’s not. One way to help you open up and get talking is to have a list of deep conversation starters that get to the heart of your specific ‘ship—questions that touch on the past, present, and future of not just your dynamic, but who your partner is as an individual. Because even though you might think you know everything there is to know about them—their goals, likes and dislikes, favorite memories—people change! And keeping in constant, evolving conversation can be instrumental in helping you grow together.
It’s also not totally necessary to be in an exclusive relationship to ask deep questions. Having meaningful conversations is a great way to really get to know someone, whether it’s your first date or your casual partner. Enter: Our master list of meaningful, deep conversation starters and questions to ask the people in your life, from your friends to your date to your long-term exclusive partner. Keep this list bookmarked, copy and paste if you’re chatting over text, and pull them out when the occasion best calls for it. Ensure that you and the other person are both in the right mindset, at peace, and excited to get to know each other better for optimal bonding. And when you’re done, you might just find that you feel more close and comfortable with this person than before. Now go forth, and get talking.
Deep Conversation Starters for Someone New
- If you could live anywhere in the world, where would you live?
- If money were no object, what would you do for a living?
- Is your current job what you always dreamed of doing?
- What’s your relationship like with your parents?
- Do you have any siblings? What’s your relationship like with them?
- Who is your hero?
- Who do you think knows you better than anyone else?
- If you could invite any three people over for dinner, living or dead, who would you invite?
- Who is your best friend? How did you meet them?
- What’s your happiest memory?
- What’s the most beautiful place you’ve ever been to?
- Tell me about your most embarrassing moment.
- What are your hobbies, and why do they matter to you?
- What’s your most prized possession and why?
- Have you ever seen a movie or TV show, or read a book that you really identified with? Why?
Deep Conversation Starters for a Date
- What kind of relationship are you looking for?
- What about me made you want to swipe right? (Or ask me out—depending on how you met.)
- Tell me about your last relationship.
- Why did your last relationship end?
- What qualities do you think make a good partner?
- Tell me about the best date you’ve ever been on. What about the worst?
- Where do you see yourself in five years?
- What are your thoughts on marriage?
- What about children?
- What’s your love language?
- What do you think makes us compatible?
- Tell me about your first kiss.
- Who was your first crush?
- Have you ever cheated or been cheated on?
- Are there any questions you’re too nervous to ask me?
Deep Conversation Starters for a Partner
- What do you love best about me?
- When did you first realize you were in love with me?
- What do you love most about our life together?
- What is your favorite date we’ve ever been on?
- Is there anything about our relationship that you wish were different?
- How do you feel when we fight?
- How do you feel about our communication habits?
- What can I do to be a better partner to you?
- Are we still aligned on our vision for the future?
- Is there anything you wish I knew or understood better about you?
- What’s the hardest thing we’ve gone through together?
- How do you see our relationship changing in the next five years?
- Is there anything you learned from your parents or relatives about love and family?
- Are you happy with our sex life?
- Is there anything we haven’t tried in the bedroom that you’d want to?
Deep Conversation Starters for a Friend
- What do you love most about our friendship?
- When did you know we’d be great friends?
- Is there anything about our friendship that you would change?
- Have I ever done anything to upset you that you didn’t address with me at the time?
- How can I be a better friend to you?
- What’s the happiest memory you have of our friendship?
- Do you feel like I really listen to you?
- What do you think makes us so compatible as friends?
- What moment between us has made you laugh the most?
- Have there been any moments between us that have ever made you sad?
- How do you describe our friendship to others?
- Is there anything you’ve learned from me?
- How do you see our friendship changing in the next five years?
- Do you think we’d be as close as we are now if we had met at a different time in our lives?
Deep Conversation Starters to Resolve an Argument
- What about this situation makes you angry?
- What prompted this argument?
- What are you really trying to say?
- What do you need from me to make you feel supported and heard?
- This issue is important to me too. How can we reach a compromise?
- Do you feel like we’ve been in this situation before?
- What can we do to resolve this once and for all?
- Is there something we can do long-term to solve this issue?
- Is there anything I can do to communicate better when we argue?
- Is there something we can do on a regular basis to improve our communication habits?
- Is there anything we haven’t addressed or gotten out right now?
