Unlock his heart: Top Online Dating Questions to Ask Him

Unlock His Heart: Top Online Dating Questions to Ask Him

online dating questions to ask him

Despite many people using online dating, it’s still intimidating for most of us. So, we have mixed and matched the top online dating questions to ask him during the first date.

We know that there’s always uncertainty regarding the identity of the person on the other end of the screen and whether a genuine connection will occur during an in-person meeting. Nevertheless, there are ways to gain insight into the person before deciding to meet in person.

One of the advantages of online dating is the ability to have a conversation with someone before meeting them in person. By maintaining an open and straightforward dialogue, you can determine whether the person is someone you can have a good time with and establish a safe and enjoyable dating experience.

However, the effectiveness of online dating conversations depends on the type of questions asked before the first date.

Online Dating Questions to Ask Him

Women frequently have the desire to cut to the chase and ask men direct questions to avoid wasting time. However, men don’t see it that way. They tend to feel uncomfortable and interrogated in such cases.

That is why it is crucial to maintain a relaxed and cheerful demeanor while keeping your approach subtle.

The online dating questions to ask him below will help you make a positive first impression and eliminate the need for awkward conversation fillers. So, continue scrolling and take a look at these insightful and engaging questions.

Questions to check if you vibe together

”We share the same vibe” – That’s one of the first things you say to your best friend when telling him about the guy you started talking to online.

You and your match can hit it off right from the start of your conversation. However, there may be times when it takes several conversations to feel like you’re heading in the right direction.

To be able to vibe with someone depends primarily on your personality. Therefore, you would know and “feel” it best throughout the conversation if you share the same vibe with someone.

To initiate the conversation, you can use some of the following basic questions:

  1. What kind of music do you like?
  2. What channels or videos do you watch on YouTube?
  3. Would you describe yourself as more of an introvert or extrovert? 
  4. Which is your 2023 / go-to Meme?
  5. Are you a mountain or beach kind of person?

Sharing the same vibe with someone can be the spark of something special. These simple questions can help determine if he might be your special someone who will know what you’re thinking without having to say it out loud.

Questions To Find Out What He Does For Fun

Questions To Find Out What He Does For Fun

Starting the conversation with light-hearted questions is an excellent approach. At the same time, you get to find out if he is a person you’d enjoy spending all your free time with.

Asking about his favorite hobbies, movies, or TV shows can reveal a lot about a person’s personality and what they like to do in their free time. For instance, if he loves hiking, it could indicate he is adventurous and enjoys the outdoors. Or, if he is into romantic comedies, it might suggest he has a sensitive side and appreciates humor.

Some of the funny online dating questions to ask him are:

  1. If you could spend all day doing something fun, what would you do?
  2. What is your favorite thing to do on your days off?
  3. What are you watching on Netflix these days?
  4. What does a perfect weekend look like for you?
  5. Ideally, how would you spend your birthday?

It’s also essential to keep in mind that compatibility goes beyond shared interests. Questions that reveal your match’s values, beliefs, and goals can provide more insight into whether you have a genuine connection.

However, asking about their life goals, what they are passionate about, or what they are looking for in a relationship can give you a glimpse into their mindset and compatibility potential.

Questions About Values and Beliefs

Establishing a friendly atmosphere is key when talking online to someone new, but it’s also important to take time and get below the surface level if you’re looking for a life partner.

Therefore, to establish a lasting connection you must delve deeper and determine if an emotional, intellectual, and spiritual aspect is compatible.

You can ask some of the below questions to find out his values and beliefs:

  1. Do you believe in God? 
  2. Do you believe people are inherently good? 
  3. What are your core values and principles?
  4. What are your beliefs about life and its purpose?
  5. What are your thoughts on *add a topic close to your heart*?

Engaging in deep conversations is an excellent way to initiate a genuine and meaningful connection with someone.

Questions About Values and Beliefs

When you ask thought-provoking questions, you show an interest in the other person’s thoughts, feelings, and beliefs, which can create a foundation of trust and understanding. Such conversations can help you learn more about the person, including their values, interests, and experiences. As you share your perspectives and listen to theirs, you can discover commonalities and differences that may strengthen the relationship.

Deep conversations can also create a comfortable atmosphere where people feel safe to share their vulnerabilities, which can help deepen the connection even further. So if you’re looking to build a more meaningful relationship with him, don’t be afraid to ask deep questions.

Questions About Life Experiences and Adventures

When it comes to online dating questions to ask him, asking about their sense of adventure is a must. Our life experiences and adventures shape who we are, and to truly understand a person, it’s important to delve deep into his life through thoughtful questioning. This will allow you to gain a comprehensive understanding of their personality.

While there are many different questions out there, you can ask some of the below questions that would help you to get a better understanding of his character:

  1. What is the most challenging thing you’ve ever done?
  2. What was the best vacation you ever took and why?
  3. What is your biggest fear in life? 
  4. If you could relive one day in your life, what day would it be and why?
  5. What’s one thing you wish you could unhear\unsee? 

Each question you ask is like taking a step closer to uncovering the essence of their heart and discovering what truly matters to them. Therefore, take the time to ask deep, thought-provoking questions that can lead to meaningful conversations and reveal whether he is the right partner for you.

Questions About Life Experiences and Adventures

Questions About Personal Growth and Self-Improvement

Forming a successful relationship doesn’t require just finding someone to connect with. It’s also important to find an individual who is dedicated, confident, and motivated to grow. Taking the time for self-improvement can have positive impacts on both parties, allowing you and your partner to progress together and be successful through life’s journey.

Some of the questions you can ask him regarding this aspect are:

  1. What’s an essential part of your daily routine?
  2. Which habit are you proudest of breaking?
  3. What are you learning these days?
  4. Which aspect of your personality do you think needs improvement?
  5. Do you wake up in the morning ready to go or hit the snooze button 5 times? 

By asking these seemingly simple questions, you can gain valuable insight into his current actions and efforts to improve themselves. You may get responses that are hopeful hopes that a person strives towards, but it’s crucial to only consider the reality of what he’s doing now to genuinely achieve those aspirations.

Questions About Personal Growth and Self-Improvement

Questions to Find Out His Views On Money

Studies have revealed that financial differences are often a make-or-break factor for couples, with 30% of those between 35 and 49, and 28% of the 25 to 34 year old’s splitting due to money issues.

These statistics suggest that financial compatibility is an essential factor in any romantic relationship. When couples have differing attitudes toward money management, it can lead to conflicts over spending habits, savings goals, and financial priorities. This can create a significant strain on the relationship, particularly if the issues persist over time.

That is why it is important to find out his views on money right from the start so that you avoid any headaches later on.

Some of the questions you can open as a topic to see his perspective on money are:

  1. Do you budget your income?
  2. What do you waste money on?
  3. What is your opinion on debt?
  4. If you won 100K right now, what would be the first thing you’d do?
  5. Do you have a Savings Fund? 

Asking these questions can provide valuable insights into your potential partner’s financial outlook and help you determine if you are a good match when it comes to managing money.

Questions to Find Out His Views On Money

Questions About Dating and Relationships

You may wonder as to why we’ve left this important part for the end. It’s essential to remember that relationship compatibility should not be a starting point. Instead, take the time to get to know someone as an individual first – their character and personality traits are key elements in ultimately discovering if you two can thrive together romantically.

Some of the questions to ask someone you met online are:

  1. What do you look for in a partner?
  2. What do you think is the biggest challenge in a relationship?
  3. What are your weaknesses in a relationship?
  4. What is the most important quality of a partner?
  5. What is your philosophy on love and relationships?

As a final note on this part – although you may be tempted to ask him about past relationships when getting to know him, it’s important to be mindful of the other person’s feelings and boundaries. While there is no inherent mistake in asking about someone’s past relationships, it’s important to remember that everyone has different comfort levels when it comes to discussing their personal history.

To avoid making him feel uncomfortable or pressured, it’s often best to refrain from asking about past relationships unless they bring it up themselves.

Questions about the future

  • What are your long-term goals and aspirations? How do you envision your life in the next five or ten years?
  • How do you think advancements in technology will shape our daily lives in the future? Are there any particular technological developments you’re excited about or concerned about?
  • Climate change is a critical issue facing our planet. How do you feel about environmental sustainability, and what steps do you think individuals and societies should take to address it in the coming years?
  • If you could travel to any point in the future, what time would you choose and why? What do you hope to see or experience during that journey?
  • As the world becomes more interconnected, cultural diversity and understanding become essential. How do you see yourself contributing to promoting tolerance and inclusivity in the future?


In conclusion, asking the right questions when getting to know someone through online dating can be a game-changer.

By engaging in meaningful conversations, you can evaluate if they are someone who shares the same values and qualities that match what you are looking for in your relationship.

Keep in mind that everyone has their unique experiences and perspectives, so don’t judge their responses without fully understanding where they are coming from.

Also, remember that online dating is just a starting point, and the ultimate goal is to move towards building a real-life connection with your potential partner with a first date. Therefore, once you’ve established a level of comfort and rapport, it’s essential to move beyond online communication and plan to meet in person.

In summary, use these top online dating questions to guide your conversations and get a sense of whether you and your potential partner have the compatibility and chemistry to pursue a healthy relationship.



More articles: