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What To Talk About on a First Date

Do you remember your first date? The excitement, the preparation, stressing out over what to wear…. I think it’s safe to say that most of us have had that experience.

My client—let’s call her Brenda—remembers her first date quite well. Not because it was full of romantic moments that led to a great love story, but because she panicked in the middle of dinner, excusing herself to call her friends. “There I was, sitting in a bathroom stall,” she recalls, “clutching my cell phone and begging for advice on how to talk to this guy.” Brenda had spent hours making sure she looked her best, only to find herself unprepared for the challenges of starting a conversation, asking questions, or communicating effectively with the person sitting across the table.

I’ve heard plenty of plenty of stories to know that a first date can go pretty well if the energy is right and chemistry is in the air. But not everyone has that luxury. That’s why I always make sure my clients are fully prepared before meeting a potential life partner.

For those struggling to find first date conversation topics, I’ve devised a few starters to ease the pressure and allow you to get to know each other better.

Here are nine questions and topics to discuss on a first date:

1. What were you like as a child? Share some interesting and exciting memories with me.

You’d be surprised how many people love to share stories from their childhood. You’d also be surprised how many people never ask about them on a first date. In addition to being a fun conversation starter, sharing memories provides insight into someone’s personality, level of maturity and self-reflection, and life goals.

Just remember that you’ll be expected to answer the question as well, so be sure to have something interesting to share in return. Whether it’s a fun prank you pulled in school or what you and your friends used to do during the summer, make it fun and memorable. Of course, not everyone had a happy childhood. If that’s you, and you’re still dealing with the trauma of your past, treat the first date as an opportunity to show far you’ve come.

This is also a perfect moment to share some of the nicknames you had growing up. Don’t worry if it’s a little embarrassing; we all have those moments. You’ll also show a willingness to reveal sides of yourself that most people don’t get to see.

2. What’s on your bucket list? What would you like to do and where would you like to go next?

You can learn many things about someone by asking them about their dreams and aspirations. Whether you’re spontaneous or like to plan things down to the minute, you probably have a bucket list of your own.

Asking your date about their bucket list will unveil hidden qualities and passions you wouldn’t have been able to guess otherwise. Maybe they want to start their own restaurant or shop, swim with sharks in the Maldives, or build a school for underprivileged children in India. Ask the question and really listen to the answers; you’re sure to learn many things about your date.

3. What’s your favorite hobby?

man surfing as a form of hobby
This may sound like a cliché question, but it’s a vital one to ask. More than in icebreaker, it will also shine a light on your date’s interests and talents. Ask what books they read last, their favorite sport, and whether they prefer movies or TV shows. Find out what genres they prefer, too.

Asking about hobbies is an easy way to see whether you and your date have shared interests. It might even give you some creative ideas about what to do on a second date…or a third. Are you both into action movies? Do you both love hiking on weekends? The only way to find out is to ask.

4. Tell me more about your family.

Most people love talking about family and reminiscing about their childhood. This particular conversation starter can reveal much about your date’s parents, siblings (if they have any), and home life. If they’re not close to their families, talk about that instead. Either way, be sensitive.

Family is important, so pay attention to how the conversation goes. Devote some time to discussing family trips, unforgettable moments, and favorite memories. The answers will help you better understand your date by giving insight into the people who raised and shaped them.

5. If you won the lottery tomorrow, where would you go or what would you do?

This is a super fun question and will give you an idea about what’s important to your date. You’ll find out whether they’re adventurous, sensible, or intelligent. It will also reveal how close their life is to the one they dream of having. If they’re successful and happy with their current lifestyle, they probably won’t want to make any drastic changes.

While it seems like a basic question, you might be surprised by some of the answers you hear. Consider how your date reacts and what they think about the future. I guarantee you’ll learn a lot about their character.

6. Do you have any fears? What are you most afraid of?

snake in a hand of a person
These are more personal questions and excellent conversation starters, especially when you want to connect with your date on a deeper level. You may get the usual answers, such as heights, spiders, snakes, tight spaces, or the dark. If the conversation is going well, you could get a more intimate response related to childhood, career, or a present struggle.

For example, your date might tell you they’re afraid of getting fired or not living their life to the fullest. Asking about fears is also an effective way to gauge the comfort level you’re building with your date. Depending on the mood of the conversation, you might find yourself revealing some things you’ve never admitted to anyone.

You can also share some fears you’ve had in the past and how you’ve overcome them to become a stronger person, thus showing your ability to adapt and learn from life’s hardships. By talking about such things, you might even help each other overcome a mutual fear.

7. Name three things you can’t live without.

If at any point you find the conversation lagging, try asking your date to reveal three things they can’t live without. It’s a quirky question that will show your fun side and put the person across from you on the spot in a positive way. Not only will you discover what they appreciate most in their lives; you’ll also learn how their minds work, how quick they are to respond, and how creative they can be on the spot.

To be sure, this is a far more interesting question than asking your date about what they do for a living. A question like this will make you laugh and bring out a more playful side in both of you. And when it comes time to answer the question yourself, avoid giving any cliché answers, such as “my phone” or “lipstick.” This is an ideal moment to step outside your comfort zone a bit and show your date a different side to who you are.

8. What are the little things that boost your mood?

Whether it’s dancing to a favorite song, making comfort food, or simply walking around the park, we all have little routines that make our days better.

Start by telling your date about the things you did today. If you already feel a connection, you can share more personal details or emotions. For example, you can talk about what you sing while in the shower and maybe even belt out a few lines to make the conversation even more enjoyable. Don’t be shy. If you want your date to go well, try to be as relaxed as possible. If your date seems introverted, try to ease the pressure by being open and non-judgmental. They might be more nervous than you!

9. If you could go out to dinner with someone, living or not living, who would it be?

This is the classic dinner question, and some would say it’s outdated. I disagree. You’ll learn a lot about your date and whether they have love and appreciation for history, are familiar with famous singers and actors, or had a strong relationship with a lost family member.

Ask them why they chose the person they did and what questions they would ask. Would they go to a restaurant or would they cook dinner at home? What kind of food would they eat? Italian, sushi, or Mexican? The answers are endless and will lead to in-depth conversations, allowing you to learn more about what interests them. Don’t forget to answer the question yourself and be as creative as possible.

First dates don’t have to be uncomfortable or embarrassing. Every person you go on a date with has something to share. Even if your date doesn’t turn out to be a home run, it’s worth listening to every word. Enjoy the conversation and have a good time. Ask some of the questions above and see where they take you.