46 Fresh Conversation Starters To Try on Your Next Date
Are you tired of going on dates and having the same conversations over and over again about food, drinks, travel, your favorite sports teams, hiking, etc.? Do you feel like you're just stuck on the same date again and again – even though the people are different?
Hey, listen, I realize that these topics make for decent icebreakers (and some people have genuine passion in these areas). I don't mind starting with these topics to warm up to someone new. But wouldn't you prefer to dive into more stimulating topics that help you really get to know your date and discover their endearing qualities and quirks?
I know I do.
As a curious and impatient person, I dislike having small talk for too long. I've cultivated a practice of asking people specific, open-ended questions that help me get to know a person beyond the surface level and increase the odds of having genuinely enjoyable conversations.
This practice of asking open-ended questions deliberately and then intently listening is highly beneficial in the dating text. It helps you figure out whether you’re talking to someone who wants a real relationship or is wasting your time. It will also help you build a stronger bond with your date (after all, people love talking about themselves and feel seen, heard, and understood when someone takes the time to ask them thoughtful questions and listen).
Below, I've listed my favorite questions to ask someone on a date by key topic areas. I’ve also provided my take on the insights you can gain about a person from these questions – so you become a good judge of character. I hope you find your favorites that bring more fun, bonding, and meaning to your dates.
Caveat: My lived experiences inform my perspective on dating. I am a college-educated Chinese-American woman who lived in coastal cities in the U.S. for all her adult life. My advice may be less relevant for those dating in very different contexts from mine. If you disagree with certain opinions of mine, discard that part and take what's helpful from the rest.
Hobbies and interests
Questions to ask:
If you could be the world champion of any hobby without having to do any of the hard work to get there, what hobby would you choose and why? Would you wear a sparkly “Champion” belt for it?
What hobby have you always wanted to try but haven't had the chance to yet?
Are there any particular skills you’re currently trying to improve?
What’s a memorable trip or adventure you’ve been on recently?
Do you have a favorite way to unwind after a busy week?
Do you have a favorite local spot for [activity they enjoy]?
Is there a hobby or activity you enjoy that surprises people when you tell them about it?
What’s something you’re looking forward to in the coming months?
Have you been to any exciting events or concerts lately?
Have you watched any great movies, listened to great podcasts, or read any good books recently?
What you’re looking to learn: Does this person have any hobbies and interests outside of work? Do they know how to relax? Do you have enough shared interests with this person to sustain a relationship? Will any of their hobbies lead them to an early death? Are they a hobby “snob” (e.g., someone who won’t take you seriously if you don’t spend $50K trekking the South Pole for your vacation)?
When to get concerned:
When someone says they have specific hobbies but haven't done them in a long time because they've been so focused/busy at work. While it's okay for someone to talk about their work, if work is the topic mentioned more than anything else, this is a sign that they likely prioritize work above all else in their life and aren't willing to make enough time to spend with you (I learned this lesson after dating two workaholics).
When someone has hazardous hobbies and is unwilling to compromise even if their family expresses concerns for their safety (e.g., race-car driving, hang-gliding, etc.)
Vision, Life Goals, and Core Values
Questions to ask:
If you could choose a theme song that plays every time you walk into a room, what song would it be, and why would this be your theme song?
Are there any causes or social issues that you feel strongly about?
What’s something you’re really passionate about and why?
How do you define success, and do you think you've found it?
What does your future life look like regarding your career, lifestyle, or personal achievements?
What’s something you’d like to change about the world, and why?
What book/movie/TV show has significantly influenced your thinking?
What was the last big, important decision you made? How do you usually make important decisions?
What dream have you had for a long time, and what are you doing to achieve it?
What would you do with it if you were given $10 million?
What you're looking to learn: Does this person have a vision for their life? Do they know what's most important to them? What drives them to pursue the things they pursue? Does their outlook on life and core values generally align with yours? Is this someone who wants the same things as you in life? Are they totally content living in their parent's basement for the rest of their life?
When to get concerned:
When someone seems to pursue a goal with such a singular focus (e.g., getting rich), they're willing to neglect all the other aspects of their life (e.g., friends, family, exercise, etc.).
When you are puzzled by what someone truly cares about because they've said conflicting things (e.g., they may not know their priorities or be lying to you).
When someone (over 21) seems completely aimless in life and has no plans to ever move out of their parents/grandparents’ basement.
Influential Figures and Family Upbringing
Questions to ask:
Of your family members, who are you closest to and why?
Is there a favorite family tradition that you enjoyed growing up?
How would you describe your family in three words?
Share a place that holds special meaning for you and your family, then ask: Is there a place with special meaning for you and your family?
What is one of your favorite childhood memories?
Were there any hobbies or activities you did often with your family growing up?
What's something you'd like to thank your parents (or guardians) for teaching you?
Who has been the most significant influence on you, and why?
What you’re looking to learn: Who has been most influential in their life? How close are they with family members? Is raising a family of vital importance? Did they have any extremely challenging/complex/traumatic experiences in their family? Are they thoughtfully choosing a partner, or just looking to marry the hotter/younger version of their mother?
When to get concerned:
When someone is not close to even one member of their family.
When they have negative relationships with most or all of their family members.
When someone absolutely values having a large family, you want zero kids.
When someone insists that their elderly mother/father will live in your shared home when you value having distance between yourself and the in-laws (and your own parents).
Romantic Relationship History
Some people are not willing to discuss their relationship history with someone they just met. Wade in the water slowly by starting with the light-hearted questions (“What’s the most bizarre date you’ve ever been on?”). Save the more serious questions (“How do you like to show affection in a relationship?”) for later, once you’ve established a rapport with someone.
Questions to ask:
What’s the most bizarre/funniest date you’ve ever been on?
What’s the most ridiculous reason why you ended a relationship?
How do you think your experiences in love have shaped your views on relationships?
If you could give your younger self one piece of dating advice, what would it be?
In your opinion, what are the key ingredients to a successful relationship?
How do you like to show affection in a relationship?
What's something you feel is essential to maintain in a relationship?
Do you think your ideas about love and relationships have evolved over the years?
Looking back, what would you say you’re most grateful for from your past relationships?
How do you approach conflicts or disagreements in a relationship?
If your love life was a movie, what genre would it be and who would play you?
What you want to learn: How does this person define a successful relationship? Does this person have the capacity for self-reflection and growth? Can they take responsibility for their role in the messes they made? Can they work with their partner through conflicts? Do they feel optimistic/believe that a healthy relationship is possible? Do they have a victim mentality? Did they have trouble getting along with all people of your gender (e.g., their exes, mom, boss, etc.) in their lives, except for you?
When to get concerned:
If you hear someone blaming and bad-mouthing all of their exes, never admitting to a single mistake in their past relationships, and not thinking they've learned anything from their exes.
If this person says they haven't been in any relationships because "all they've had is bad luck."
If you start to get their sense that this person lacks respect for all people of your gender.
Finances
Since money can be a particularly sensitive topic for people to discuss, you may get better results by sharing first and then asking your date the same question.
Questions to ask:
What’s the best piece of financial advice you’ve ever received? Do you have any favorite budgeting apps or tools that you use?
Have you ever had a side hustle (or side project that also helps you earn extra cash)?
[Lead with sharing first]. How do you balance saving for the future with enjoying the present?
What would you do with the money if you won a small lottery?
What’s something you’d like to learn that might also be a good investment in yourself?
How do you approach large purchases? Are you a planner or more of an impulse buyer?
Do you have a cause or charity you’re passionate about and like to support?
What you want to learn: Do you and this person have wildly divergent views on earning, saving, and spending money? Do they have good money sense? What, if any, values/meaning are they attaching to cash? How much money is enough for them to be happy? Are they running up credit card debt because they can't stop buying clothing for their avatar in a VR game?
Now, you may get along great with someone with a different outlook on finances than you. But at a minimum, you need to understand the truth of the situation and be alright with their approach to money. For dating-related expenses, both sides should agree on how much it is okay to spend on a date and how the bill gets settled.
When to get concerned:
When someone wants to spend a lot more money on luxury dates than you are comfortable with and won’t compromise on doing activities that are within your budget.
If someone is a penny-pincher and constantly complains about everything being too expensive.
If you get the sense that the person spends more than their earnings on material things to impress others.
When someone likes to brag about how much they make.
If you get the sense this person is pursuing wealth at the expense of everything else (e.g., health and good relationships).
Tips On Using These Questions Successfully
Use your best judgment on when to broach a sensitive topic like finances. For instance, I personally choose to avoid the subject of finances on a first date. Also, make sure to work these questions naturally into your conversation. Don’t act like it’s an interrogation or job interview, and show genuine interest in their responses by asking follow-up questions when appropriate.
With this, I am signing off. I’d love to hear your experience with trying these questions on a date.