Has the cat got your tongue? Lost for words? Here are 50 questions that you can ask to get to know someone better, these are conversation starters and deep questions which will strengthen connections.
By Wendy Rose Gould
SHOWING curiosity and genuine interest in others is one of the quickest ways you can build a connection with someone. This is true whether it’s the first time meeting a new person or in long-term relationships. What’s more, science has told us over and again that friendships, social connections, and meaningful partnerships make us happier and can improve our mental well-being.
Taking time to invest in these relationships is worth your while, and sometimes all it takes is a simple question. Whether you’re putting yourself out there in new social situations or hoping to nourish existing connections, these 50 platonic and romantic questions can help you get to know someone better and help strengthen your relationships.
10 Basic Questions to Break the Ice
Maybe you’re new to the office, are on a first date, or are heading to a meetup for the first time. These scenarios can feel intimidating and some conversations can even turn a bit awkward, and that’s perfectly normal.
These ice breaker questions can help lighten things up and get the conversation rolling:
- What’s your idea of a perfect vacation?
- Have you watched any TV shows or movies recently that you’d recommend?
- What’s one food you’ve tried but would never eat again?
- What’s the ideal way you like to spend a wide-open weekend?
- What’s the most recent book or article you’ve read that captured your interest?
- Have you ever won an award or contest?
- If you could have dinner with anybody in the world from across history, who would it be and why?
- If you could have any superpower, what would it be?
- Alive or passed—and money no issue—which musician would you love to see perform live?
- What’s the cheesiest joke you’ve ever heard?
10 Questions to Spark Further Conversation
These questions are perfect in scenarios whether you’re just getting to know someone or you’ve chatted here and there and want to get to know them even better. They’re a bit deeper than the questions in our ice breaker section, and can technically work in all kinds of scenarios:
- Where’s your favorite place you’ve ever traveled?
- What’s the best advice you’ve ever received?
- If you could give a 10-minute presentation on any subject, what would it be?
- What’s the best compliment you’ve ever received from someone?
- What’s the number one thing you wish more people knew about you?
- Has a random stranger ever made a really big impact on you?
- Do you have an evening or morning ritual? Why are these steps important to you?
- What’s the most exciting thing you’ve done recently?
- Do you speak any other languages? If so, how did you learn it? If not, which would you pick to learn first?
- Who has the biggest influence on you in your life right now?
10 Questions About Hopes, Dreams, & Fears
Asking people about their hopes, dreams, and fears taps into a part of them that they may seldom talk about with others. It also gives you a chance to get to know them better, and even serves them, in a way, since it invites them to ponder deeper questions:
- What’s the number one priority for your lifetime?
- What’s your best advice on how to deal with failure?
- How do you motivate yourself when you’re feeling stuck?
- What’s a flaw you see in yourself that you’re currently working on?
- What’s something that scares you, but you do it anyway?
- Do you see yourself living somewhere else in the future? Where and why this place?
- What’s a mistake you made in the past that you’ve learned from?
- What’s something you’ve accomplished that you’re extremely proud of?
- What is something you fear the most in life?
- How have your goals or dreams changed over time?
10 Questions to Strengthen Friendships
Even after a friendship is established, it’s important to remain curious about the other person and make sure you’re tapped into each other’s lives. This is true whether your friend lives in town or across the country.
These questions can help strengthen your friendship and keep dialogue pathways open:
- I love spending time with you. Do you want to get together soon?
- How can I be a better friend to you?
- When you’re sharing something hard that you’re going through, do you prefer that I just listen or offer advice?
- What was your first impression of me, and how has it changed?
- Do you feel like you can be your full self when we’re hanging out?
- What do you value most about our friendship?
- What’s a short or long-term goal you’re working toward right now? Can I help in any way?
- Do you feel like you can always trust me to be there for you?
- Is there anything creating a lot of stress in your life right right now? Do you want to talk about it?
- What do you think is the key to a meaningful, life-long friendship?
10 Questions to Foster a Deeper Romantic Connection
Romantic relationships have a tendency to burn hot and then cool a bit as we get used to each other.
This cooling is actually beautiful, and shows that we’ve become comfortable with the other person.
Still, it’s important to maintain open dialogue and make a consistent effort to spark romance:
- Is there anything I can do to better support you and help you grow?
- What attracted you to me in the beginning?
- What’s something I’ve done that has pushed you away or made you feel like creating distance between us?
- What’s your favorite form of physical intimacy? Are you receiving enough of it?
- When have you felt the most loved by me?
- When we’re together, what makes you feel your sexiest?
- When were you the most proud of me?
- What romantic or sexual fantasies do you have?
- Is there anything I do that upsets you, and what do you need from me instead?
- If you could relive any moment from our past again, what would it be and why?
Whether a first meeting, burgeoning friendship, or established relationships, sometimes a simple question can make all the difference. Use these questions to help foster stronger connections with the people in your life and reap the rewards of deeper connection and meaningful, life-long relationships.
