Best Questions To Ask on Dating Apps
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79 Best Questions To Ask on Dating Apps (2024)

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Ask your match these questions to start an engaging conversation and see if your chemistry is off the charts.

Starting conversations on online dating apps can be a fun yet overwhelming (and sometimes kind of awkward) experience. The key to breaking the ice and cultivating a deeper connection lies in the art of asking thoughtful questions that will spark engaging conversations.

Discover a treasure trove of thought-provoking questions for your dating app conversations. Uncover the depths of your potential match with these engaging and flirtatious conversation starters. From playful banter to deep discussions, ignite meaningful connections through captivating dialogue.

Whether you’re Looking for love, companionship, or new connections; these questions will guide your conversation towards true understanding and shared interests.

Good Online Dating Questions to Ask

With the help of dating experts and a lot of research, I’ve curated a list of the best questions to ask on a dating app, that will take your online dating conversations from novice to pro!

RELATED: 40+ Icebreaker Questions for Tinder

Intriguing Icebreaker Questions

An Icebreaker question is always a great way to start a conversation, whether you’re meeting someone new or looking to deepen existing relationships. Here are some intriguing icebreaker questions for a dating app; designed to spark curiosity, laughter, and thoughtful exchanges.

  1. What’s an unexpected hobby or interest you have?
  2. If you could live in any era, which one would it be and why?
  3. What’s the most spontaneous thing you’ve ever done?
  4. What song best describes your life right now?
  5. What’s one book that has profoundly affected you?

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Relationship Compatibility Questions

Assessing compatibility on a dating app is crucial for building a strong, lasting relationship. Here are questions designed to explore various dimensions of compatibility, including values, lifestyle choices, and future aspirations.

  1. What kind of music, movies or books do you enjoy? 
  2. Do you have any pets?
  3. How do you like to spend your weekends?
  4. Are there any causes or social issues that are important to you? 
  5. What are your goals for the future?

Avoiding Red Flags and Deal-Breakers

Navigating the online dating world requires awareness of one’s own boundaries and the ability to identify potential red flags and deal-breakers in relationships. Ask a question from the list below to better recognize deal-breakers and avoid red flags.

  1. Can you tell me about a life-changing experience or event?
  2. How do you handle challenges or setbacks in life?
  3. What are some long-term goals or aspirations that drive you?
  4. How do you define success in a relationship?
  5. What role does communication play in your ideal relationship?

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Get-to-Know-You Questions

Getting to know someone new can be an exciting journey, filled with discoveries and shared stories. Here are some engaging get-to-know-you questions designed to reveal insights about personality, preferences, and life experiences.

  1. What’s one thing you’re looking forward to in the next month?
  2. If you could learn one new skill overnight, what would it be?
  3. What’s a passion project you’re currently working on?
  4. How do you like to spend a rainy day?
  5. What’s a tradition you love in your family?

Unique Childhood Questions

Exploring someone’s childhood through questions can offer unique insights into their formative years, highlighting experiences and memories that have contributed to their current self. Here are thoughtfully crafted questions to uncover those childhood treasures.

  1. What was your most treasured possession as a child?
  2. Did you have a childhood dream that you still remember vividly?
  3. What childhood game were you unbeatable at?
  4. Who was your childhood hero, and why?
  5. What’s a funny or embarrassing childhood story you’re willing to share?

Deep Personal Questions

Delving into deep personal questions can significantly enhance understanding and connection, revealing core beliefs, values, and experiences that shape a person. Here are some questions designed to facilitate profound conversations and foster intimacy.

  1. What does your ideal day look like from dawn to dusk?
  2. What’s a challenge you’ve overcome that you’re proud of?
  3. What’s a belief you once held strongly but have since changed?
  4. How do you find peace or relaxation in stressful times?
  5. What’s one thing you’ve done that pushed you out of your comfort zone?

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Fresh Dating History Questions

Discussing dating history freshly and constructively can offer insights into preferences, relationship patterns, and what one is looking for in a partner. Here are some thoughtful questions designed to explore dating history without delving into uncomfortable territory.

  1. What’s a lesson you’ve learned from a past relationship?
  2. How do you think your closest friends would describe your approach to relationships?
  3. What’s something small that matters to you in a relationship?
  4. How do you feel about making the first move?
  5. What’s a relationship deal-breaker for you?

Light-Hearted Fun Questions

Injecting a dose of humor and light-heartedness into conversations can make interactions more enjoyable and memorable. Here are some fun questions designed to spark laughter, share amusing thoughts, and keep the mood upbeat.

  1. If you could instantly become an expert in something, what would it be?
  2. What’s the worst fashion trend you participated in?
  3. If you could have dinner with any fictional character, who would it be and why?
  4. What’s a silly fear you have?
  5. What’s the most unusual food you’ve tried and liked?

Personality-Revealing Questions

Understanding someone’s personality can offer profound insights into their thoughts, behaviors, and preferences. Here are some questions designed to reveal deeper aspects of a person’s character, fostering a closer connection and better understanding.

  1. How do you unwind after a long day?
  2. What’s a small thing that can make your day better?
  3. What are you currently curious about?
  4. What personality trait do you value most in others?
  5. How do you express creativity in your life?

Discovering “Favorites” Questions

Discovering someone’s favorites is a delightful way to learn about their tastes, preferences, and even some aspects of their personality. Here’s a list of questions that aim to uncover the favorites of someone you’re getting to know, sparking engaging and often revealing conversations.

  1. What’s a movie you can quote from start to finish?
  2. Who’s an artist or band you think deserves more recognition?
  3. What’s an adventure you’re dying to go on?
  4. What’s a dish you can cook that you’re proud of?
  5. What’s a recent discovery you’ve made that you’re excited about?

Engaging Deep Questions

Engaging in deep conversations can significantly strengthen the bond between two people, offering insights into each other’s values, beliefs, and aspirations. Here are some thought-provoking questions designed to encourage profound reflection and meaningful connections.

  1. If you could witness any event past, present, or future, what would it be?
  2. What’s something you believe everyone should try at least once?
  3. What does success mean to you?
  4. What’s a piece of advice you’ve received that has stuck with you?
  5. How do you hope to make a difference in the world?

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Flirty and Fun Questions

Injecting a bit of flirtation and fun into conversations can elevate the mood and bring you closer to someone you’re interested in. Here are some flirty and playful questions designed to spark a bit of chemistry and laughter.

  1. What’s something you find irresistible in a person?
  2. How would you describe your flirting style?
  3. What’s something you’re good at that might surprise me?
  4. If we were on a deserted island, what’s one thing you’d bring to impress me?
  5. What’s a compliment that you’ve received that made you blush?

Ask “Would You Rather?” Questions

“Would You Rather?” questions are a fantastic way to break the ice, spark creativity, and delve into the preferences and thought processes of someone you’re getting to know.

  1. Would you rather have the ability to talk to animals or speak all foreign languages?
  2. Would you rather live in a treehouse or a cave house?
  3. Would you rather travel to space or explore the depths of the ocean?
  4. Would you rather have a rewind button or a pause button on your life?
  5. Would you rather experience life in the future or relive a part of the past?

Intimacy-Building Questions

Building intimacy in a relationship goes beyond physical closeness, touching on emotional connection, mutual understanding, and shared vulnerability. These questions are designed to encourage deeper intimacy, allowing you both to explore each other’s thoughts, feelings, and desires in a meaningful way.

  1. What makes you feel appreciated and loved in a relationship?
  2. How do you express affection and love?
  3. How do you communicate your needs in a relationship?
  4. What are some ways we can build trust and deepen our connection?
  5. What’s something you feel is key to maintaining passion over time?

Trust-Building Questions

Building trust in any relationship, whether new or established, is crucial for a deep and lasting connection. Asking thoughtful and open-ended questions can significantly contribute to this process, encouraging openness and vulnerability. Here are the top trust-building questions for online dating.

  1. How do you feel trust is best built and maintained?
  2. Can you share a time when your trust was broken and how you dealt with it?
  3. How do you prefer to resolve conflicts or misunderstandings?
  4. In what ways do you show someone you trust them?
  5. Is there something you’ve never shared because you were afraid of being judged?

Dating History Questions

Navigating discussions about past relationships requires sensitivity and timing, ensuring both parties feel comfortable and respected. Here are additional questions that tread thoughtfully into the realm of dating history, designed to foster understanding and connection without overstepping boundaries:

  1. What’s one lesson you’ve learned from your dating experiences?
  2. Is there a trait or behavior you’ve found you’re particularly compatible or incompatible with?
  3. In retrospect, is there anything you would have done differently in your past relationships?
  4. Can you share a moment from a past relationship that was particularly meaningful to you?
  5. How do you know when you’re truly compatible with someone?

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Ask an Open-Ended Question

An open-ended question is a powerful way to spark meaningful conversation, allowing for in-depth responses and a deeper understanding of one another. Here are some thoughtfully crafted open-ended questions to ask that encourage sharing, reflection, and connection:

  1. “Can you share a moment or decision that significantly changed your life’s direction?”
  2. “What’s something you’ve always wanted to do but haven’t, and what’s holding you back?”
  3. “Can you tell me about a person who has been a significant influence in your life?”
  4. “How do you recharge or take care of yourself after a stressful period?”
  5. “What are some dreams or goals you’re working towards right now?”

Questions to Get to Know a Guy

Getting to know a guy you’re interested in can be an enriching experience. The key to unlocking the depths of his personality, interests, and values lies in asking him the right questions. Here are the best online dating questions to ask him.

  1. What qualities do you look for in a woman?
  2. Who are the most important women in your life currently?
  3. Who is your biggest celebrity girl crush?
  4. What’s your biggest turnoff?
  5. If women were cars, what would be your favorite manufacturer and model?

To truly connect with someone on a dating app, you need to dive into meaningful conversations. 

Ask about their favorite travel destination or most unforgettable concert. Explore love at first sight and what they look for in a partner.

These thought-provoking questions will ignite captivating discussions that transcend surface-level chitchat. No more relying solely on profile pictures and bios – it’s time to find genuine connections. 


Hayley’s Expert Advice

It’s important to remember that questions aren’t the only way to build a connection with someone. Sharing statements, and talking about yourself, your hobbies, interests, and passions can build a lot of trust. It can also help to generate a naturally flowing conversation. So make sure all your interactions are balanced between asking the person questions and also actively sharing information about yourself.

In regards to asking questions, my advice would be to only ask questions you care about knowing the answer to. For example, don’t waste time asking a load of questions about pets, if you’re not a pet person. Instead, consider what would make you more attracted to and excited about the person, and let that guide the questions you ask.

Hayley Quinn

Hayley Quinn

London’s Expert Dating Coach


Mastering Your Conversations

Engaging in meaningful conversations on dating apps goes beyond just asking good questions. Here are some expert tips to help you truly connect with someone:

  • Be fully present and eliminate distractions when chatting on a dating app.
  • Show genuine curiosity by asking follow-up questions based on their responses.
  • Avoid generic replies and share personal anecdotes or experiences related to the topic at hand.
  • Use humor appropriately, aligning your jokes with both your and your match’s sense of humor.
  • Share personal stories to encourage your match to do the same, fostering trust and vulnerability.
  • Be respectful in every interaction, treating everyone with kindness and courtesy.
  • Take turns asking questions and showing curiosity about your match’s life experiences.
  • Listen actively, paying close attention to not only what they say but also how they say it.

By following these expert tips, you can elevate your conversations on dating apps and increase your chances of forming genuine connections. Remember, it’s not just about asking good questions; it’s also about actively engaging with the other person and showing them that you’re interested in getting to know them better.


Strategies for Keeping Conversations Going on Dating Apps

StrategyDescriptionTips
Show Genuine InterestAsk questions based on their profile or messages to demonstrate your attentiveness and interest in them.Focus on details they’ve shared to formulate thoughtful questions.
Share About YourselfBalance asking questions by sharing your own experiences and thoughts, inviting a two-way exchange.Share stories or experiences related to the topic at hand to deepen the connection.
Be CuriousUse open-ended questions to encourage more detailed responses and keep the dialogue flowing.Avoid yes/no questions; instead, ask “How?” “Why?” or “What are your thoughts on…?”
Use HumorLight-hearted jokes or playful comments can make the conversation more enjoyable and less formal.Keep it respectful and appropriate, ensuring it aligns with the tone of the conversation.
Find Common GroundIdentify and expand on shared interests, values, or experiences to create a sense of connection and provide more topics to discuss.Mention any hobbies, passions, or experiences you both share and explore these further.
Keep It PositiveMaintain an overall positive tone to make the conversation more enjoyable and engaging.Share positive experiences or uplifting thoughts, but be authentic.
Be ResponsiveShow engagement by replying in a timely manner, which encourages a dynamic exchange.Aim for timely responses but also respect each other’s time and availability.
Suggest PlansIf the conversation is going well, suggesting a related activity can move the connection from online to in-person.Propose a casual, low-pressure activity that relates to your shared interests.
Stay OpenBe open to discussing a wide range of topics, even unexpected ones, to discover new areas of compatibility.Embrace the natural flow of the conversation, even if it takes an unexpected turn.
Respect BoundariesUnderstand and respect when they are not comfortable discussing certain topics, and adjust the conversation accordingly.If they indicate discomfort with a topic, gracefully change the subject.

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