From lighthearted prompts to deeper topics, here’s how to build a connection from the very first conversation
On a first date with someone you like—perhaps even a potential partner—the right questions can help break the ice, spark conversation, and open the door to getting to know a new person. According to psychologists, the best questions are open-ended ones that encourage more than a simple yes or no answer. On a first date, that matters most.
How to Choose the Right Questions for a First Date
Choosing your questions thoughtfully can help you understand the other person’s personality, values, and interests. It also helps the conversation flow naturally and leaves a strong first impression. Regardless of personality differences, these psychologist-approved tips can help you break the ice and create a genuine connection.
Fun and Light Questions
What’s your favorite food?
What does your ideal weekend look like?
What’s the most fun thing you’ve done recently?
How do you like to relax after a long day?
Who is your favorite celebrity?
What was your dream job as a child?
What kind of music do you listen to?
What’s your favorite book, movie, series, or podcast?
Do you prefer being outdoors or staying in?
What’s the best trip you’ve ever taken?
What’s the strangest dream you’ve ever had?
What’s one thing you never leave the house without?
What’s your favorite place in the world?
What’s the most embarrassing nickname you’ve ever had?
What’s the biggest adventure you’d like to experience?
What’s the funniest thing that’s ever happened to you on vacation?
What’s your hidden talent?
What’s the most unusual food combination you’ve tried that turned out to be surprisingly good?
Do you have a favorite word?
What’s the most unbelievable fact you know that always amazes people?
Questions About Traits, Values, and Personality
What do you think is your best quality?
What’s your biggest weakness?
What does “home” mean to you?
What’s your favorite childhood memory?
Who are your role models?
What’s your relationship like with your family?
How do you define happiness?
Where do you see yourself in five years?
What goal are you currently working toward?
What’s the biggest challenge you’re facing right now?
How do you imagine retirement?
What skill or quality would you like to develop in yourself?
Have you ever had a moment that changed your perspective on life?
What do you consider your greatest achievement so far?
What’s the hardest thing you’ve ever gone through?
How do you cope with stress or sadness?
What are you most grateful for?
What’s the best advice you’ve ever received?
What’s your worst habit?
If you could change one thing about yourself, what would it be?
These questions can help you get to know each other better and foster a sense of closeness. Research and real-life experience show that people feel more connected through deeper conversations rather than surface-level small talk.
Questions to Keep the Conversation Going if It Stalls
If the conversation slows down, hypothetical questions can help get things moving again:
If you had a superpower, which one would you choose?
If you could travel anywhere in the world right now, where would you go?
If you could switch places with someone for a day, who would it be?
If you had three wishes, what would you wish for?
If you could witness any historical event, which would you choose?
If you could have dinner with anyone (living or dead), who would it be?
If you could invent something right now, what would it be?
If you could befriend any animal, which one would it be?
Which movie best represents your life?
Which actor or actress would you choose to play you in a sitcom about your life?
Studies show that while long pauses can feel awkward early on, they don’t prevent a conversation from developing well later. The right questions can help turn those moments into natural pauses for shared reflection.
Other Helpful Questions
Many great questions will arise naturally during the conversation. At times, you may want to ask about things that matter to you in terms of compatibility—just be mindful of boundaries and privacy.
What do you value most in a friendship or relationship?
Are there any topics or causes that are especially important to you?
What are you looking for in a relationship—casual, serious, long-term?
Do you prefer calling your partner or texting?
How do you maintain a balance between work and personal life?
What do you enjoy doing when you want to unwind?
Tips for a Successful First Date
A first date can be both exciting and nerve-racking—and that’s completely normal.
“Feeling nervous before a first date is perfectly natural,” says Sabrina Romanoff, a clinical psychologist specializing in relationships.
She also shares a few practical tips:
Keep a small list of conversation topics: Even having it saved on your phone can help you relax.
Listen actively: Show interest, ask follow-up questions, and avoid prying.
Don’t make it feel like an interview: Focus on interests, values, and experiences—not a résumé.
Aim to genuinely get to know the person: Discover what makes them happy.
Look for common ground: Shared interests naturally deepen conversation.
Avoid unrealistic expectations: See the first date as a chance to decide if you want a second one—not a compatibility test.
Don’t try to prove yourself: You’re there to choose as much as to be chosen. Let the conversation unfold naturally.
With the right questions and mindset, a first date can be not just memorable—but meaningful.
