20 must-ask questions to reveal a guy’s true intentions (without making it awkward)

Woman getting to know his intentions
Woman getting to know his intentions
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He walked into the room, his smile disarming, but his intentions? A mystery. That’s when I realized the importance of asking the right questions to truly understand where a guy’s head—and heart—might be. Figuring out questions to ask a guy to know his intentions isn’t just about ticking boxes; it’s about sparking conversations that reveal his values, his dreams, and yes, his deal breakers.

I’ll share a story about my best friend, who almost missed the signals with someone she thought was perfect. It taught us both that the right questions can turn uncertainty into clarity.

I’m Claire Delli Santi, and if there’s one thing I’ve learned, it’s that curiosity—handled gracefully—can change everything.

And, if understanding his intentions intrigues you, you’ll love learning how to make a man chase you effortlessly—don’t miss it!

Key Nuggets


Getting Started: Setting the Foundation

Before diving into the questions, it’s essential to establish a solid foundation for open communication. Building trust and establishing a comfortable environment will encourage your partner to share their true intentions. Here are some tips to keep in mind:

  1. Create a Safe Space: Ensure that your partner feels comfortable expressing their thoughts and emotions without fear of judgment or rejection.
  2. Be Honest and Vulnerable: Open up about your own intentions and desires, which will encourage your partner to reciprocate.
  3. Choose the Right Timing: Timing is crucial when asking personal questions. Wait until you’ve established a deeper connection before delving into more intimate topics.
  4. Active Listening: Pay attention to not only what your partner says but also how they say it. Non-verbal cues can provide valuable insights into their true intentions.

With these foundational principles in mind, let’s explore the best questions to ask a man to know his intentions.




Which Questions Should You Ask a Guy to Know His Intentions?

When it comes to questions to ask a guy to know his intentions, it depends on the stage of your relationship. In the early stages, it’s important to ask about his interests and goals.

As your relationship progresses, you can ask about his values and long-term plans. Be wary of red flags such as reluctance to commit and inconsistent behavior.

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Just-Started Dating Questions: Gauging Interest

When you’re in the early stages of dating, it’s important to keep the questions light and casual. You want to get to know your partner without overwhelming them with intense inquiries.

Here are some questions to gauge his interest and understand what he’s looking for:

1. What are you looking for in a partner?

By asking about his relationship goals, you can gauge if they align with yours. It’s crucial to pay attention to his response and see if it matches what you desire in a committed partnership. To delve even further into his intentions, consider asking deeper questions about his life goals and aspirations.

For example, you could ask him about his career ambitions or what he hopes to achieve in the next five years. This will help you understand him on a deeper level and determine if he’s a compatible romantic partner.

2. Where do you see yourself in three or five years?

Asking about future plans can provide insights into his long-term goals and priorities. If he mentions marriage and starting a family, it’s a positive sign that he’s open to a committed relationship.

However, if his plans involve extensive travel or personal pursuits, it may indicate that he’s not ready to settle down. Understanding a person’s aspirations can help determine if their intentions align with yours and if a deep connection is possible.

For instance, if he expresses his desire to build a stable and loving home, it suggests that he values a serious commitment and is looking for more than just a casual relationship. Additionally, by asking this question, you can gain a better understanding of his biggest fear, whether it’s failure, loneliness, or something else entirely.

3. Are you seeing anyone else?

This question is crucial in understanding his dating habits and the level of commitment he has towards you. By asking this question, you can gauge if he is casually dating or looking for something more serious.

It also helps establish boundaries and avoids any potential awkwardness or confusion down the line. For example, if he responds by saying he’s exclusively seeing you, it’s a positive sign that he views you as a potential partner and is not interested in pursuing other relationships simultaneously.

4. What are your main priorities in life?

By asking this question, you can gain insight into his values and what he deems significant. If he mentions family, career, or personal growth, it shows that he is dedicated to creating a stable and fulfilling life.

This alignment could be crucial if you’re looking for a quality time partner who shares your aspirations. Knowing his priorities ensures that you’re both on the same page, setting the foundation for a potential exclusive relationship.

For example, if he expresses regret in life for not pursuing his passion for music, it reveals his desire for real-life experiences and adds depth to your conversation.

5. What’s your stance on long-term relationships and marriage?

By discussing his views on long-term relationships and marriage, you can uncover his beliefs about commitment. If he expresses a positive outlook on long-term partnerships and values the institution of marriage, it suggests he’s open to a committed relationship.

On the other hand, if he dismisses the idea of marriage, it may indicate that he’s not looking for a long-term commitment. Understanding his perspective on this topic can provide insight into his intentions regarding romantic relationships. Follow-up questions can include asking about his ideal woman and what he envisions in a long-term partnership.

For a deeper conversation, you can inquire about his thoughts on personal growth within a relationship and how he navigates challenges. For example, you can ask, “Have you ever been in a relationship where you had to overcome some major issues? How did you handle it?”

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6. Have you ever been in love before?

Asking about his past experiences with love can provide valuable insights into his emotional attraction and reveal his intentions when it comes to relationships. By inquiring about his history, you can gauge his openness and capacity for deep connections.

If he willingly shares details about previous relationships and expresses a genuine desire to find love again, it’s a positive sign that he’s ready for a committed partnership. On the other hand, if he avoids the topic or dismisses the notion entirely, it could indicate a preference for casual dating or a lack of emotional readiness.

A similar question may be: “Tell me about a time when you were truly in love and how it shaped your perspective on relationships.”

7. What was your last relationship like?

Understanding his past relationships can provide insight into his emotional maturity and approach to romantic partnerships. By asking this question, you can gauge how he handles conflicts, communicates, and resolves issues within a relationship.

It can also reveal his biggest regret or relationship deal breaker. For example, he might share that his last relationship ended because of a lack of trust or a fundamental disagreement on future goals.

This question allows you to explore his past experiences in a non-judgmental manner, giving you a better understanding of his intentions and compatibility.

8. If you could have three wishes for the next year, what would they be?

This lighthearted question can provide valuable insights into a guy’s aspirations and desires, shedding light on his future plans and priorities.

By actively listening to his response, you can gauge whether his wishes align with your own goals and values, which is crucial for a successful relationship. For instance, if he wishes for personal growth, a stable career path, and a loving relationship, it indicates a positive mindset and a desire for personal and professional growth.

On the other hand, if his wishes revolve around material possessions or involve harmful intentions, it might be a red flag indicating bad intent.

9. Are a lot of your friends in serious relationships?

This question can provide valuable insight when getting to know a guy’s intentions. By exploring his social circle, you can gather clues about his attitude towards commitment.

If you notice that many of his friends are in committed relationships, it indicates that he values long-term partnerships and may be more inclined to pursue a serious relationship himself. This can be a positive sign if you’re looking for a partner who is ready for a committed and lasting connection.

For example, if he shares stories about how his friends go out of their way to plan romantic gestures for their partners or engage in deep conversations about their future together, it shows that he is surrounded by individuals who prioritize love and dedication in their relationships.

10. Do you have any deal-breakers when it comes to relationships?

Understanding his deal-breakers can help you gauge his compatibility and identify any potential red flags. It’s crucial to discuss your own deal-breakers as well to ensure a healthy and fulfilling relationship.

The # 1 Secret When Attracting a Man?

Here comes a powerful yet little-known principle. Men’s primal instinct, known as the “hero instinct“, refers to a powerful innate drive within men to feel like “heroes” in their relationships (I’m not talking about superheroes here, of course). It is a deep-rooted desire to protect, provide, and be needed by their partners.

By understanding and triggering this instinct, you can create an intense emotional connection with your man and make him crave you on a deeper level. Relationship coach James Bauer, best-selling author of “His Secret Obsession,” has developed a simple, science-based principle that taps into this instinct, but many women are unaware of its existence.

Thankfully, James Bauer offers a brief instructional video that explains this principle in an engaging and easy-to-understand manner. By watching this video, you can gain valuable insights into how to trigger your man’s hero instinct and make him truly desire you.

With James Bauer’s guidance, you can attract the man you always wanted, strengthen your relationship and create a lasting bond based on mutual love and admiration.

Click here to play the video

Deepening the Connection: Questions for Established Relationships

Once you’ve passed the initial dating phase and are in a more established relationship, it’s essential to have deeper conversations to gauge long-term compatibility. Here are some questions to ask a guy to know his intentions in a committed relationship:

11. Where do you see our relationship headed?

This direct question allows you to understand his thoughts and expectations for the future of your relationship. It’s important to have open and honest communication to ensure both partners are on the same page.

12. How do you feel about the current status of our relationship?

Asking about his feelings regarding the relationship provides an opportunity for open dialogue and understanding. It allows both partners to express their needs and desires, fostering a stronger emotional connection.

13. How do you feel about marriage?

If marriage is a goal for you, it’s crucial to discuss this topic with your partner. Understanding his thoughts and feelings about marriage will help determine if your relationship aligns with your long-term goals.

14. What are your long-term goals and aspirations?

Discussing long-term goals and aspirations can help you understand if your partner’s vision for the future aligns with yours. It allows you to assess compatibility and determine if you can build a life together.

15. Have you introduced me to your friends and family?

Introducing your partner to friends and family is a significant step in a committed relationship. If he hasn’t introduced you to his loved ones, it’s essential to discuss his reasons and understand his level of commitment.

16. What are your thoughts on starting a family?

If starting a family is important to you, discussing this topic is crucial. Understanding his thoughts and desires regarding children will help you determine if you’re compatible in the long term.

17. How do you handle conflict in relationships?

Understanding his approach to conflict resolution is essential for a healthy and successful relationship. Discussing this topic allows you to assess his emotional intelligence and ability to communicate effectively.

18. What are your financial goals for the future?

Discussing financial goals can help you determine if you’re aligned in your approach to money and long-term financial planning. It allows you to assess compatibility in one of the most critical aspects of a committed relationship.

19. Do you have any fears or insecurities in relationships?

Opening up about fears and insecurities can foster deeper emotional connection and understanding. It allows both partners to support each other and work through any challenges that may arise.

20. What is your ultimate relationship goal?

Asking about his ideal vision of a long-term, committed relationship can provide valuable insights into his intentions and desires. It allows you to assess if his goals align with yours and if you’re both striving for a similar future.

You may like: 7 Steps to Attract a High Value Man Into Your Life, Plus 5 Red Flags to Watch Out For

Questions to Absolutely Avoid

Here are five “deadly” questions you should absolutely avoid asking when getting to know a guy’s intentions while in the early stages of dating:

  1. “Are you just looking for a casual fling?” – This question may put pressure on the person and make them feel judged. It’s best to let the relationship develop naturally without assuming their intentions.
  2. “Why haven’t you settled down yet?” – Asking this question can come across as judgmental and may make the person feel defensive or inadequate. It’s important to respect their personal journey and not make them feel pressured.
  3. “What are your plans for marriage and kids?” – This question can be seen as intrusive and may make the person feel like they’re being interrogated. It’s best to let these topics come up naturally in conversation rather than forcing them.
  4. “Do you see a future with me?” – Asking this question too early in a relationship can create unnecessary pressure and make the person feel trapped. It’s best to focus on building a connection and enjoying the present moment.
  5. “Are you seeing other people?” – While it’s natural to be curious about exclusivity, asking this question too soon can make the person feel like they’re being interrogated. It’s important to give the relationship time to develop before discussing exclusivity.

My Take

A few years ago, my friend—a fiery, creative spirit working in marketing—found herself swept off her feet by a man who seemed perfect on paper. They’d met at an art gallery, bonded over their shared love for abstract expressionism, and the chemistry was palpable. But weeks in, she was left wondering where things were headed. That’s when she turned to me, asking, “How do I figure out what he really wants without sounding, you know… too much?”

We brainstormed questions to ask a guy to know his intentions—gentle yet revealing. The magic lay in tone and timing, not interrogation. One evening over wine, she casually asked about his five-year vision. His vague, non-committal response hinted that his life was more about the moment than the long haul. That realization helped her make an empowered choice, moving on with clarity instead of false hope.

This reminded me of James Bauer’s His Secret Obsession guide and his hero instinct theory. It’s genius for understanding what drives men emotionally—especially for those looking for actionable results. I always recommend it to women seeking deeper connection, minus the costly coaching sessions. Because sometimes, the right questions can save your heart and your time.