52 Interesting Things to Talk About on a Date Breaking The Ice

52 Interesting Things to Talk About on a Date: Breaking The Ice

Written by: Casey Bennett

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Time to read 17 min

Perhaps you went on a date like this where the conversation dragged on forever? Maybe. That’s as much fun as watching paint dry, isn’t it? However, it doesn't have to be thus. With a few tricks up your sleeve and a bit of charm, you can transform a potentially awkward situation into an enjoyable chat-fest.


So, what's the big secret? It's all really rather straightforward. Basically, if you have a number of fascinating things to talk about on a date, your audience will be riveted. And you know what, I've got 52 of these awesome subjects right here for you. Yes, that's right-52! New topics for a chat through dinner, drinks, or a rendezvous under the moon.


Now, you might be thinking, "52 topics? That's a lot to remember!" Never fear, I'm here to help you out. We'll start with some casual conversation starters and work up to the really juicy stuff. By the end of this guide, you'll be ready to strike with lightning-fast conversational one-liners, just waiting for the next time you go out on a date.

Why Is Good Conversation So Important?

Okay, let's get real for a minute. Why should you worry about having good conversation on a date? For starters, it's better than sitting in tense silence, racking your brains trying to think of something - anything - to say.

But on top of that, good conversation is like the secret seasoning of dating. This is what it will do for you:

  • Help you decide if this is someone you really click with

  • Create an atmosphere that's easy-going and fun

  • Show the world what kind of an awesome person you are

  • Actually make it fun for you (imagine that!)

Just like that, and to be totally honest, if you can carry on an excellent conversation then you are already a step ahead of half the field when it comes to dating. It is a skill you will be happy to possess, no matter if this is your first date or your fiftieth.

What type of ice cream flavor would you like the most

Breaking the Ice

Let's kick things off with some light-hearted questions to break the ice and set a fun tone for your date.

1. What type of ice cream flavor would you like the most?

This quirky question can reveal a lot about a person's personality and sense of humor. Are they a classic vanilla, a bold Rocky Road, or an adventurous lavender honey? Their answer might surprise you!

Suggested follow-up: "That's interesting! What made you choose that flavor?"

2. If zombies rushed in right now, what would be the first thing you'd grab as a weapon?

Nothing brings people together like planning for the zombie apocalypse, right? This question not only sparks creativity but can also lead to fun discussions about survival skills or favorite zombie movies.

Suggested follow-up: "Good choice! Have you ever thought about what you'd do in a real emergency?"

3. What's your perfect day?

This question gives insight into what your date values and enjoys. It's a great way to discover shared interests or learn about new activities you might want to try.

Suggested follow-up: "That sounds amazing! What's stopping you from having more days like that?"

4. Are you an early bird or a night owl?

A simple question that can reveal a lot about daily habits and lifestyle preferences. It might even help you plan future date ideas!

Suggested follow-up: "I'm curious, has this always been the case for you, or did it change over time?"

5. If you could have one superpower, what would it be?

Who doesn't love a bit of fantasy? This question taps into imagination and can lead to fun discussions about superhero movies or comic books.

Suggested follow-up: "That's a cool power! How would you use it in everyday life?"

6. What's something weird or embarrassing you did as a kid?

Sharing funny childhood stories is a great way to bond and show vulnerability. Plus, it usually leads to lots of laughter!

Suggested follow-up: "That's hilarious! Did you get caught?"


Remember, the key to using these questions effectively is to listen actively to your date's responses and ask follow-up questions. This shows that you're genuinely interested in what they have to say and helps keep the conversation flowing naturally.


Now that we've broken the ice, let's dive deeper into some engaging topics that will help you and your date really get to know each other. In my experience, discussing childhood memories, personal passions, and travel adventures can lead to some of the most interesting conversations on a date. Ready to explore?

What was your favorite subject in school

Childhood and Family

Our childhood experiences shape who we are. By asking about your date's early years, you can gain insight into their background and values. Here are some questions to get you started:

1. What's your best childhood memory?

This question often brings up heartwarming stories and can reveal what your date values most from their past.

Suggested follow-up: "That sounds wonderful! How do you think that experience shaped you?"

2. What was your favorite subject in school?

Their answer might hint at their natural talents or interests that have carried into adulthood.

Suggested follow-up: "Interesting! Do you still pursue that subject as a hobby or in your career?"

3. What did you want to be when you grew up?

This can lead to fun discussions about childhood dreams and how they compare to current realities.

Suggested follow-up: "How does that compare to what you're doing now? Are you happy with where you ended up?"

Who

4. Who's the funniest person in your family and why?

This question invites your date to share a lighthearted story about their family while giving you insight into their sense of humor and family dynamics. It's a fun way to learn about their relatives without diving too deep too quickly.

Suggested follow-up: "That sounds hilarious! Do you have a favorite funny moment with them you can share?"

5. Do you have any siblings?

Sibling relationships can be a goldmine for funny stories and insights into your date's personality.

Suggested follow-up: "What was it like growing up with them? Were you close?"

6. What was your childhood home like?

This question can reveal a lot about your date's upbringing and the environment that shaped them.

Suggested follow-up: "That's fascinating! Do you think where you grew up influenced who you are today?"

Are you reading anything interesting at the moment

Passions and Interests

Talking about passions is a great way to see your date's eyes light up. It's also an opportunity to find common interests. Here are some questions to explore:

1. What are you really good at?

This question allows your date to showcase their talents and feel good about themselves.

Suggested follow-up: "That's impressive! How did you discover this talent?"

2. What do you do to keep growing in [their area of interest]?

This shows you're interested in their personal development and can lead to discussions about goals and aspirations.

Suggested follow-up: "That's a great approach. Have you ever considered teaching others about this?"

3. Do you have any hobbies that you've recently started?

New hobbies can be exciting to talk about and might even give you ideas for future dates.

Suggested follow-up: "What made you decide to try that? How are you finding it so far?"

4. What's your favorite way to spend a day off work?

This question can reveal a lot about their lifestyle and what they value in their free time.

Suggested follow-up: "That sounds perfect! When was the last time you had a day like that?"

5. Are you reading anything interesting at the moment?

Book discussions can lead to deep conversations about ideas, beliefs, and worldviews.

Suggested follow-up: "What do you think of it so far? Has it changed your perspective on anything?"

6. Do you have any unique hobbies?

This question might uncover fascinating interests that you wouldn't have thought to ask about otherwise.

Suggested follow-up: "Wow, I've never heard of that before! How did you get into it?"

What

Travel and Adventure

Travel stories can be some of the most interesting things to talk about on a date. They reveal a person's sense of adventure, cultural interests, and life experiences. Let's dive in:

1. What's your dream destination?

This question can spark conversations about bucket lists and future plans.

Suggested follow-up: "That sounds amazing! What draws you to that place?"

2. Have you ever been camping? What was your favorite part?

Camping stories can be fun and reveal how comfortable they are with nature and roughing it.

Suggested follow-up: "I love that! Would you be up for a camping trip in the future?"

3. Would you rather spend a week in New York City or Los Angeles?

This can lead to discussions about preferences for big city life, east coast vs. west coast, or urban vs. rural settings.

Suggested follow-up: "Interesting choice! What do you think you'd do there for a week?"

4. What kind of trips are your favorite?

Their answer can reveal a lot about their travel style and preferences.

Suggested follow-up: "That sounds like my kind of trip too! What's been your best experience with that type of travel?"

5. What's the most interesting place you've traveled?

This often leads to fascinating stories and insights about different cultures.

Suggested follow-up: "Wow, I'd love to hear more about that! What was the biggest surprise about visiting there?"

6. What's the most amazing adventure you've been on?

Adventure means different things to different people. Their answer can reveal a lot about their risk tolerance and what excites them.

Suggested follow-up: "That sounds incredible! How did that experience change you?"


Remember, the key to making these questions work is genuine interest and active listening. Use their answers as springboards for further conversation, and don't be afraid to share your own experiences too. After all, the best dates feel less like interviews and more like the start of a great friendship... or maybe something more!


As we continue our journey through engaging date conversations, let's explore some lighter topics that can reveal a lot about a person's tastes and imagination. In my experience, discussing entertainment, food, and hypothetical scenarios can lead to some of the most interesting and fun conversations on a date. Ready to dive in?

What

Entertainment and Pop Culture

Entertainment preferences can tell you a lot about a person's personality and interests. Here are some questions to spark engaging discussions:

1. What TV shows are you watching right now?

This can reveal their current interests and potentially lead to recommendations you both might enjoy.

Suggested follow-up: "That sounds intriguing! What do you like most about it?"

2. What's your all-time favorite book?

Books often hold a special place in people's hearts and can lead to deep conversations about ideas and emotions.

Suggested follow-up: "Interesting choice! How has that book influenced you?"

3. What's the best live music show you've ever been to?

Music experiences can be incredibly personal and memorable. This question often leads to exciting stories.

Suggested follow-up: "Wow, that must have been amazing! What made it so special?"

4. Which movie could you watch over and over again?

This can reveal a lot about their taste in stories, humor, or even their comfort films.

Suggested follow-up: "I love that movie too! What's your favorite scene?"

5. If you could be a character from a hit television show, who would you pick?

This question allows for some fun role-playing and can reveal which character traits they admire.

Suggested follow-up: "Great choice! What do you like most about that character?"

6. What's your go-to karaoke song?

Even if they don't like karaoke, this can lead to discussions about favorite songs or amusing anecdotes.

Suggested follow-up: "I'd love to hear that! Do you have any funny karaoke stories?"

Are you a good cook

Food and Culinary Experiences

Food is not just sustenance; it's an experience that can bring people together. Here are some questions to explore your date's culinary preferences:

1. What food is your guilty pleasure?

This light-hearted question can reveal a fun, indulgent side of your date.

Suggested follow-up: "That sounds delicious! Do you have a favorite place to get it?"

2. What's the best meal you've ever had?

Great meals often come with great stories, whether it's about the food, the company, or the location.

Suggested follow-up: "That sounds incredible! What made it so special?"

3. Are you a good cook?

This can lead to discussions about favorite recipes, cooking disasters, or potential future date ideas.

Suggested follow-up: "I'd love to try your cooking sometime! What's your signature dish?"

4. Do you prefer sweet or savory dishes?

A simple question that can reveal a lot about their palate and potentially lead to favorite recipe exchanges.

Suggested follow-up: "Interesting! What's your absolute favorite [sweet/savory] dish?"

If zombies attacked, what would be your plan

Hypotheticals and Imaginative Scenarios

Hypothetical questions can be some of the most interesting things to talk about on a date. They reveal how a person thinks and what they value. Let's explore some thought-provoking scenarios:

1. If you could live to 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?

This question can lead to deep discussions about aging, health, and what we value most in life.

Suggested follow-up: "That's a fascinating choice! How do you think that would change your life?"

2. If you could wake up tomorrow having gained any one quality or ability, what would it be?

This reveals aspirations and values, and can lead to interesting conversations about self-improvement.

Suggested follow-up: "That's a great choice! How would you use that ability in your daily life?"

3. If zombies attacked, what would be your plan?

A fun, lighthearted question that can reveal problem-solving skills and teamwork abilities.

Suggested follow-up: "I like your strategy! Where did you learn those survival skills?"

4. If you could time travel, which era would you visit?

This can lead to discussions about history, scientific curiosity, or even fashion preferences.

Suggested follow-up: "Interesting choice! What would you hope to see or experience there?"

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

Their answer can reveal a lot about their values, dreams, and financial mindset.

Suggested follow-up: "That sounds amazing! How do you think that would change your life?"

6. If you could make one book or movie a reality, which would you choose?

This can lead to fun discussions about favorite stories and how they might play out in real life.


Suggested follow-up: "Great choice! What role would you want to play in that world?"

Remember, the key to making these questions work is to listen actively and share your own thoughts too. The best conversations on a date are those where both people are engaged and building on each other's ideas.


These topics - from entertainment preferences to culinary experiences and imaginative scenarios - offer a mix of light-hearted fun and potential for deeper connection. They're designed to help you and your date relax, laugh, and maybe even dream a little together.


In my experience, discussing values, playing fun psychological games, and talking about future plans can lead to some of the most interesting and meaningful conversations on a date. Are you ready to take your date conversation to the next level?

Is there a cause you

Values and Life Philosophy

Understanding someone's values and life philosophy can give you great insight into who they are at their core. Here are some thought-provoking questions to explore:

1. What inspires you to better yourself?

This question can reveal a person's motivations and what they consider important in life.

Suggested follow-up: "That's really admirable. How has that inspiration changed your life so far?"

2. If you could correct one problem in the world, what would you fix?

Their answer can show you what issues they're passionate about and how they view global challenges.

Suggested follow-up: "That's a great choice. How do you think we could start addressing that problem?"

3. What are some life goals of yours?

This question helps you understand their ambitions and what they're working towards.

Suggested follow-up: "Those are exciting goals! What steps are you taking to achieve them?"

4. What values are important to you?

Understanding someone's core values can give you insight into their decision-making process and what they prioritize in life.

Suggested follow-up: "I respect those values. Can you share an example of how they've guided you in a difficult situation?"

5. Are you a pessimist or an optimist? An idealist or a realist?

This question can lead to interesting discussions about their outlook on life and how they approach challenges.

Suggested follow-up: "Interesting perspective! How do you think that outlook has shaped your life experiences?"

6. Is there a cause you're particularly passionate about?

Their answer can reveal what they care deeply about and potentially lead to discussions about volunteer work or activism.

Suggested follow-up: "That's a worthy cause. Have you ever considered getting more involved with it?"

The "Psychological Test" Game

Now, let's try something a little different. This game can be a playful way to explore your date's self-perception and relationship views. Remember, it's just for fun, so keep it light-hearted!

Instructions:

Tell your date you have a little psychological test for them. Ask these three questions:

  1. What's your favorite animal? Describe it in detail.

  2. What's your favorite color? Describe it in detail.

  3. What's your ideal body of water? Describe it in detail.

After they answer, share the "meanings" behind their choices:

  • The animal represents how they'd like others to view them.

  • The color represents how they view themselves.

  • The body of water represents how they think about their romantic life.

Suggested follow-up: "What do you think about these interpretations? Do you feel they're accurate for you?"

This game often leads to laughter and can open up conversations about self-perception, aspirations, and views on relationships. It's one of the most interesting things to talk about on a date because it combines fun with potential for deeper discussion.

What

Looking to the Future

As your date winds down, these questions can help you gauge your connection and potentially set the stage for future meetings.

1. What's the most incredible experience you can remember?

This question allows your date to share a cherished memory and can give you insight into what they value in life experiences.

Suggested follow-up: "That sounds amazing! Would you like to have more experiences like that in the future?"

2. If we were sitting here two years from now, what would have happened in your life for you to say things are really good?

This question can reveal their hopes and dreams for the near future, and how you might fit into that picture.


Suggested follow-up: "Those are great aspirations. How do you plan to work towards them?"

3. Are you doing anything fun next weekend?

This casual question can be a natural way to gauge their interest in seeing you again.


Suggested follow-up: If they're not busy, you could say, "I know this great [cafe/park/activity] if you'd like to check it out together?"


Remember, the goal of these questions is not just to get answers, but to start conversations. Listen actively to your date's responses, share your own thoughts, and let the conversation flow naturally. These interesting things to talk about on a date are just starting points - the real magic happens in the organic discussion that follows.


As you use these questions, pay attention to how your date responds. Are they enthusiastic and engaged? Do they ask you questions in return? Their level of interest in the conversation can be a good indicator of how well you're connecting.

We'll also wrap up with some key takeaways and address common questions about date conversations. Ready to become a master of meaningful date dialogue?

If you could change anything about the way you were raised, what would it be

Arthur Aron's 36 Questions - The Fast Track to Intimacy

Have you ever wondered if there's a scientifically proven way to create a deep connection with someone? Well, psychologist Arthur Aron developed a set of 36 questions that, when discussed with a partner, can potentially accelerate intimacy. While we won't list all 36 here, I'll share a few that I find particularly intriguing:

  1. Given the choice of anyone in the world, whom would you want as a dinner guest?

  2. Before making a telephone call, do you ever rehearse what you are going to say? Why?

  3. If you could change anything about the way you were raised, what would it be?

  4. If you could wake up tomorrow having gained any one quality or ability, what would it be?

How to use these questions: Take turns answering each question. Listen actively and share openly. Remember, vulnerability often leads to deeper connections.

Suggested follow-up: After discussing a few questions, you might ask, "How do you feel these questions are affecting our conversation? Are you comfortable continuing?"

Mastering the Art of Date Conversation

As we wrap up our journey through 52 interesting things to talk about on a date, let's recap some key points:

  • Active listening is crucial: It's not just about asking questions, but genuinely engaging with the answers.

  • Be open and authentic: Sharing your own thoughts and experiences can encourage your date to do the same.

  • Follow the flow: While these questions are great starters, let the conversation evolve naturally.

  • Read the room: Pay attention to your date's comfort level and adjust your questions accordingly.

Remember, the goal is to connect, not to interrogate. Use these questions as a guide, but trust your instincts and enjoy the process of getting to know someone new.


Bonus Tip: Want to commemorate a great first date? Consider our Custom Embroidered Hoodies For Couples with Roman Numerals of your first date. It's a unique way to remember the day you first connected over these interesting conversations!

FAQs About Interesting Things to Talk About On A Date

1. What if my date isn't very talkative?

Start with lighter topics and gradually move to more personal ones. Give them time to open up and don't be afraid of comfortable silences.

2. Should I avoid certain topics on a first date?

Generally, it's best to avoid heavy topics like politics, religion, or past relationships unless they come up naturally and both parties are comfortable discussing them.

3. How can I tell if the date is going well based on our conversation?

Look for signs of engagement: Are they asking you questions in return? Laughing? Making eye contact? These are usually good indicators.

4. What if we run out of things to talk about?

Don't panic! You can always return to earlier topics and ask follow-up questions, or try one of the hypothetical scenarios we discussed.

5. Is it okay to disagree with my date on certain topics?

Absolutely! Respectful disagreement can lead to interesting discussions. The key is to remain open-minded and avoid becoming argumentative.

Casey Bennett

Casey Bennett

Casey Bennett is a Content Writer at Custommatchingcouple LLC, where she creates engaging articles and social media content to foster emotional connections with readers. With a Bachelor's degree in English Literature from UC Berkeley and four years of experience in digital storytelling, Casey specializes in crafting compelling narratives that resonate with diverse audiences. When not weaving words, Casey indulges her passion for photography and hiking, activities that fuel her creativity and provide fresh perspectives for her writing endeavors.

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