20 Questions To Ask When Online Dating

20 Questions To Ask When Online Dating

In the era of online dating, asking the right questions can be the key to finding your perfect match. 

Questions can reveal values, interests, and lifestyles, providing a sneak peek into what a future with someone might look like. Moreover, asking good questions keeps the conversation engaging, making you stand out in a sea of "hey" and "how's it going?" messages. 

As you navigate the vibrant world of dating apps, you'll want a companion that helps ensure your online dating experience is safe and secure. Enter the Burner app

Burner gives you the freedom to explore connections while maintaining your privacy, so you can focus on the exciting task of getting to know your potential partner.

What Is Online Dating and How Does It Work?

Online dating is a modern approach to finding romantic partners by connecting with them through the internet. 

Individuals can use various digital platforms like dating sites and apps to present themselves to potential partners based on shared interests, geographic proximity, age, and other criteria. These platforms have revolutionized how we meet and interact with potential partners, making it possible to connect with people outside of our immediate social circles.

Here's a simple breakdown of how it works:

  • Profile Creation: The first step is creating your profile, whether you're using a dating app like Tinder or Bumble or a dating site like OKCupid or eHarmony. This includes providing basic information about yourself — like age, location, and interests — and uploading pictures. Some sites might also include personality tests to help match you with compatible users.
  • Browsing and Matching: Once your profile is set up, you can browse other profiles based on your preferred criteria. Many apps use a “swipe” system: Swipe right if you're interested, left if you're not. When both individuals swipe right, it's a match, and a conversation can start.
  • Communicating: After matching, you can begin communicating with your match through in-app messaging. This is where you can ask questions, share more about yourself, and gauge whether you'd like to meet in person.
  • Meeting in Person: Once both parties feel comfortable, they can choose to meet in person, moving the relationship from the digital realm to the real world.

Online dating has made meeting new people easier, especially those with busy schedules or limited social circles. However, it's important to use these platforms safely and responsibly, ensuring your privacy and security while navigating the journey to find a potential partner.

What Questions Should I Ask When Dating Online?

Once you’ve matched with someone online, it’s time to get to know each other. Here are 20 different questions broken down into four categories that you can ask the person you matched with during your conversations:

Light-Hearted Icebreaker Questions

When you've just met someone online on a dating app, sparking a fun conversation is an effective icebreaker. This strategy helps create positive vibes right from the start and gives an insight into the person's sense of humor. Also, it helps set the tone for more in-depth conversations later on. 

Here are five light-hearted questions to kick-start your online chat:

1. If you could have any superpower, what would it be and why?

This question is a playful and imaginative way to learn more about the other person's desires, values, and personal philosophy. It gives them the opportunity to think outside the box and share something interesting about themselves. 

Plus, it's a fun question that can lighten the mood. A potential follow-up question could be, "How would you use that superpower in your everyday life?"

2. What's your favorite emoji, and how often do you use it?

Emojis have become a language of their own in the age of social media. The answer can reveal whether they're a jovial, more light-hearted individual, an introvert, or someone more expressive and colorful in their communication.

3. What's a nickname you've had in the past, and what's the story behind it?

Nicknames often have funny or interesting stories attached to them. This question is a great way to share a laugh and learn something unique about their past. 

A thoughtful follow-up question might be, "Do your friends or family still call you by that nickname?"

4. What's the best TV show you've binge-watched on Netflix recently?

This fun way to initiate conversation not only helps determine their taste in TV shows, but their answers could also open doors for a more in-depth discussion on pop culture, favorite genres, and even the trending shows on Netflix. 

A follow-up question could be, "What did you like most about the show?"

5. Would you rather be a night owl or an early bird?

This question can give you an idea about their daily routine and lifestyle. It's a fun yet insightful conversation starter that could lead to discussions about productivity, leisure activities, or even work habits.

Remember, the purpose of these questions is to create a good conversation, not to make it feel like a job interview. They can help you get a first impression and spot potential red flags. For example, if their favorite TV show is all about manipulation or deceit, or their desired superpower is mind control, it might be worth probing into their values and outlook.

Feel free to tailor these questions based on what you've gleaned from their online dating profile. Your next step could be to ask about their favorite book, place, or movie. The best dating experiences often start with great questions, so don't hesitate to get creative. A unique question might just be the key to unlocking a meaningful conversation and a potentially perfect date.

Questions About Personal Preferences and Lifestyle 

Understanding someone's preferences and lifestyle is vital to online dating. It can help you identify shared interests, lifestyle habits, and potential areas of compatibility or conflict. This information can assist you in deciding if there is enough common ground to warrant a face-to-face meeting

Here are five questions that can provide a deeper understanding of someone's personal preferences and lifestyle:

6. Do you prefer spending your free time indoors or outdoors?

Knowing their preferred setting can provide insights into their lifestyle and hobbies. If they enjoy the outdoors, they might be adventurous and enjoy activities like hiking or biking. They might enjoy reading, watching movies, or cooking if they prefer staying indoors. 

A follow-up question could be, "What's your favorite indoor/outdoor activity?"

7. What's your favorite place you've ever visited, and what made it special?

This question can reveal a lot about their interests and experiences. It can also provide a glimpse into their background, values, and what they enjoy doing. 

A follow-up question might be, "Where do you plan to go next, and why?"

8. Do you have a favorite cuisine or dish?

Food preferences can say a lot about a person. This question could reveal whether they're adventurous eaters, foodies, or have dietary restrictions. It's also a great way to find common ground if you both share a love for the same cuisine. 

You could follow up by asking, "Have you ever tried making it at home?"

9. What kind of music do you enjoy?

Musical preferences can be an indicator of personality and can also provide potential ideas for dates, like concerts or music festivals. 

You could follow up with, "Who's your favorite artist, and have you seen them live?"

10. What's your favorite movie, and why do you love it?

This question is a classic conversation starter that can give you insights into their taste in film, their values, or their emotional depth. The reason behind their choice can be more revealing than the choice itself. 

You might follow up with, "Is there a particular scene or character you relate to?"

Remember, people enjoy talking about themselves, especially about their likes and dislikes. Asking questions about personal preferences can lead to longer, more engaging conversations. These questions are not exclusive to dating sites; you can also ask them during your first date, leading to more personal and deep connections.

What Are Deeper Questions I Can Ask About the Past and Future?

Once you've established a good rapport, delving deeper is important. Asking more profound questions about someone's past and future can help you better understand their personality, values, and life goals. This can be invaluable for assessing your compatibility and understanding if a first date, or even a future together, could be on the horizon. 

Here are five questions that provide more in-depth insight:

11. What’s on your bucket list?

This question can help you gauge if your future goals and desired adventures align. It can provide a sense of whether they're an adventurous spirit or prefer more simple pleasures. 

A great follow-up question could be, "What's stopping you from ticking off those items?"

12. What’s the most significant accomplishment you’re proud of?

This online dating question is an opportunity for your potential partner to shine. It allows you to understand what they value most in life and what motivates them. It also opens the door to discussing their future ambitions.

13. What’s your favorite thing about the place you live?

This question can tell you a lot about what they value in a living situation. It gives insights into their lifestyle and can even hint at planning a potential first date. 

You could follow up with, "If you could live anywhere else, where would it be?"

14. Can you tell me about your last relationship?

While it's essential to tread carefully with this question, it can provide valuable insights into their past relationships. Understanding why their last relationship ended can help you identify any potential deal breakers or recurring issues. 

A sensitive follow-up might be, "What did you learn from that experience?"

15. What’s your biggest pet peeve in a relationship?

This question is a subtle way to understand their deal breakers in a relationship. Their answer will provide insights into their expectations and non-negotiables in a relationship.

 You can follow up by asking, "How would you handle that situation if it arose in a relationship?"

Remember, asking these questions can easily feel like a natural progression from your initial conversation starters. Pay attention to how they answer. Do they answer willingly, or do they seem uncomfortable? It's important to respect their boundaries as you learn about each other.

These deeper questions can help you transition from simply someone you merely met online to a potential partner. Still, online dating is a gradual process. As you progress, these good questions aid in building a stronger connection and a potentially successful relationship.

Flirty and Fun Questions To Build Chemistry

While getting to know your potential partner is crucial, you also want to keep the spark alive. Flirty and fun questions can help create chemistry, build excitement, and keep the conversation lively. These questions can give your conversation a playful twist, moving it beyond formalities and helping you both see if there’s an emotional connection. 

Here are five fun and flirty questions to ignite that spark:

16. Do you believe in love at first sight, or should I pass by again?

This is a cheeky, flirty question that can lighten the mood. It can also lead to a conversation about their feelings on instant connections and their romantic ideals.

17. What’s the most spontaneous thing you’ve ever done?

This question can bring out stories about thrilling experiences and crazy adventures. It adds a dash of excitement to the conversation and allows you to see their adventurous side. 

As a follow-up question, you can ask them, "Would you do it again?"

18. What's your idea of a perfect date?

This question flirts with the possibility of a future date, and their answer will provide valuable information about what they value and enjoy. 

You could follow this question with, "What's the best date you've ever been on?"

19. If we were at home, cuddling on a lazy Sunday morning, what would we have for breakfast? a) Bacon and eggs, b) Pancakes, c) Cereal, d) Something else?

This question flirts with the idea of you two together and reveals insights about their lifestyle and preferences. 

Keep the fun going by following up with, "Who would be the one cooking?"

20. If you could dedicate a song to our potential relationship, which one would it be and why?

This question is flirty and helps you gauge their musical taste and how they perceive the potential relationship. The reason behind their song choice can tell you more about their feelings and thoughts. 

As a follow-up question, you can ask, "What's your all-time favorite song and why?" It's a fun way to explore each other's musical landscape and can lead to deeper conversations.

The goal of these flirty questions is to lighten the conversation and infuse it with fun while providing an opportunity for both of you to express your personalities and senses of humor. 

These questions can help take your conversation to the next level, whether on dating sites or your first face-to-face date. However, always be mindful of the other person’s comfort level with the playfulness and flirtation in your conversation.

From Online Conversations to Real-World Dates

Asking the right questions in online dating is more than a quest for information; it's a journey toward understanding, connection, and possibly love. Engaging inquiries can turn routine exchanges into meaningful conversations, which can pave the way to a real-world date and potentially a long-term relationship. 

By focusing on varied questions, like light-hearted icebreakers, queries about personal preferences, deeper inquiries about past and future, and flirty, fun questions, you can foster an engaging, intriguing dialogue that helps both you and your match move forward confidently. 

As you make the leap from online conversation to meeting in person, remember to prioritize your privacy and safety with tools like the Burner app. At the end of the day, online dating should be about connecting with others while feeling secure and comfortable. 

Download the Burner app today to start your free seven-day trial and keep your personal information private. Happy dating, and good luck!


The Five Years That Changed Dating | The Atlantic

The Importance of Humor in Long-Term Relationships | Psychology Today

Emojis Are Language Too: A Linguist Says Internet-Speak Isn’t Such a Bad Thing | The New York Times

9 Things That Your Food Might Say About Your Personality | Psychology Today

The Neuroscience of Everybody's Favorite Topic | Scientific American

Ready to start calling & texting with a shiny new number?

Get Burner

Scan to download Burner