96 Questions to Ask a Guy to Know His Intentions

So you’ve met a man and you fancy him. But what are his intentions? Is he just looking for something casual, or does he want something serious? If you’re not sure, it can be really frustrating to figure out. Luckily, this list of questions can help you get a better idea of his intentions!

Relationship Views

  1. How do you define a successful relationship?
  2. What does your ideal relationship look like?
  3. How important is exclusivity to you in dating?
  4. In what ways do you think a good relationship contributes to your life?
  5. What lessons have past relationships taught you?
  6. What role does communication play in your relationships?
  7. Do you believe in labels concerning relationships? Why or why not?
  8. What are your thoughts on online dating versus traditional dating?
  9. How long do you prefer to know someone before calling it a relationship?
  10. What importance do you place on physical attraction vs. emotional connection?
  11. What’s your take on compromise in a relationship?
  12. Are there certain things you’re unwilling to tolerate in a relationship?
  13. How do you handle disagreements in a relationship?
  14. What signifies a healthy boundary to you in a relationship?
  15. How do you maintain your individuality while in a relationship?
  16. What does partnership mean to you in the context of a romantic relationship?

Interest Level

  1. What inspired you to want to get to know me better?
  2. Are you looking for a serious commitment right now or just having fun?
  3. What qualities do you find most appealing in a partner?
  4. How much time are you willing to invest in a new relationship?
  5. Do you enjoy spending a lot of time together, or do you value personal space?
  6. How do you show interest in someone you’re dating?
  7. What type of romantic gestures do you appreciate or enjoy?
  8. Can you describe what being ‘ready for a relationship’ means to you?
  9. How do you typically pursue someone you’re interested in?
  10. What made you decide to continue dating me after our first meeting?
  11. How much does a shared interest/hobby matter to you in a dating scenario?
  12. What is your typical style of flirtation? Direct or subtle?
  13. How long does it usually take you to decide if you’re interested in someone?
  14. Are there certain traits that immediately capture your attention?
  15. When you think about someone you like, how do you envision spending time together?
  16. In what ways do you prioritize the person you’re dating in your life?

Future Intentions

  1. Where do you see yourself in the next five years?
  2. Are you open to the idea of marriage or a long-term partnership?
  3. How do you feel about having children in the future?
  4. Do you have any geographical preferences for settling down?
  5. What are your career aspirations, and how do they align with your personal life?
  6. Do you foresee your dating intentions changing in the near future?
  7. How do you approach the concept of sharing a life with someone?
  8. What kind of timeline do you have in mind for significant relationship milestones?
  9. How important is it for you to have your partner’s support in achieving your dreams?
  10. Do you have any reservations about cohabitation before marriage, if at all?
  11. How does a significant other fit into your vision of your future?
  12. What steps do you take when planning a future with someone?
  13. Are you someone who wants to make decisions jointly with a partner?
  14. In terms of future planning, how proactive are you in a relationship?
  15. Do financial aspirations or plans play a role when considering a long-term partner?
  16. What changes are you willing to make for a relationship in the long run?

Core Values

  1. What values do you consider most important in life?
  2. How do your values influence your decisions in your personal and dating life?
  3. What are your thoughts on honesty and transparency in a relationship?
  4. How does your culture or background shape your values regarding relationships?
  5. Do you have spiritual or religious beliefs that are significant to you in a relationship?
  6. How do you handle conflict based on differing values?
  7. In what ways do you incorporate empathy and understanding in your relationships?
  8. What is your stance on the importance of mutual respect in a relationship?
  9. How do you balance personal growth with a partner’s needs?
  10. Can you share a value you’d never compromise on, even for someone you love?
  11. What are your views on equality within a relationship?
  12. How strongly do you adhere to your ethical or moral standards?
  13. What role does generosity play in your life and relationships?
  14. How do you navigate differences in political or social views with a partner?
  15. What values do you hope to share with your partner?
  16. How do you demonstrate commitment and loyalty in a relationship?

Red Flags

  1. Have you ever noticed patterns in your behavior that you’re actively trying to change?
  2. Can you talk about a past mistake that you’ve learned from in dating?
  3. What signs make you rethink continuing to date someone?
  4. How do you deal with jealousy or insecurity within a relationship?
  5. Are there specific things that you consider deal-breakers in a relationship?
  6. How do you respond to criticism or feedback in relationships?
  7. What behaviors do you find unacceptable from a partner?
  8. Have you ever had trust issues in a relationship, and how did you handle them?
  9. Do you think it’s important to maintain privacy in certain aspects of a relationship?
  10. How do you recognize if you’re not the right fit for someone you’re dating?
  11. What’s your approach to resolving conflicts that might be deal-breakers?
  12. Can you share a situation where you had to end a relationship due to a red flag?
  13. How do you identify and communicate your own boundaries?
  14. What actions do you consider unforgivable in a relationship?
  15. How do you ensure you don’t ignore red flags in a relationship?
  16. In what ways do you address potential red flags you see in yourself?


  1. How have you changed the most in the past few years?
  2. What aspects of your character are you currently working to improve?
  3. How do you foresee yourself evolving in the context of a relationship?
  4. What kind of personal challenges have you overcome that you’re proud of?
  5. Are you the type to reflect on your feelings regularly, or do you tend to keep busy?
  6. What experiences have shaped your perspective on love and relationships?
  7. Have your priorities shifted regarding what you’re looking for in a partner?
  8. How do you balance self-improvement with self-acceptance?
  9. What does self-care look like for you, and how do you prioritize it?
  10. How do you take ownership of your actions in a relationship?
  11. In what ways do you contribute to the growth of a relationship?
  12. What part of your life are you most content with, and why?
  13. How does your dating life reflect the person you are trying to become?
  14. What are your coping mechanisms when you face personal or relational stress?
  15. Can you discuss a time when self-reflection led to a breakthrough in your dating life?
  16. How does taking care of your mental health impact your relationships?

Frequently Asked Questions

How can you tell a man’s true intentions?

One way to determine if a man is interested in a serious relationship or just a casual fling is to look at how he behaves around you. If he always makes an effort to be around you, compliments you, and tries to strike up a conversation with you, then he’s probably interested in more than just a casual relationship.

On the other hand, if he seems rather aloof or doesn’t make much of an effort to spend time with you, then it’s probably safe to assume that he’s not looking for anything serious.

How can you tell that a man is leading you on?

It can be difficult to tell if a man is leading you on, but there are some signs to look for. If he seems genuinely interested in getting to know you but doesn’t follow through with his plans or disappears after a few conversations, he could be leading you.

If he’s always finding excuses not to meet in person or only wants to talk via text or online, that’s another sign he’s not interested in a real relationship. If you’re not sure if a man is leading you on or not, it’s best to ask him directly. If he’s honest and tells you he’s not interested, you can move on and find someone who is.

What to do when a man is unsure about you?

If a man is unsure about you, he may not be sure if he wants to pursue a relationship with you. If that’s the case, it’s best to give him some space and let him figure things out. If he does get back in touch and expresses interest in you, take things slowly and don’t rush things.

Ultimately, the decision on whether or not to pursue a relationship with this man is up to you. If you aren’t sure if he’s the one for you, it may be best to move on.

Final Thoughts

Asking these questions can really help you understand what he’s looking for. If he doesn’t want to talk about the serious stuff, it might mean he’s not thinking long-term. But if he’s open and answers everything, that’s a good sign he’s into something more serious.

Just don’t forget to watch how he acts and the way he talks—sometimes, these things can tell you even more than his words. At the end of the day, it’s all about having a real chat and seeing where things go without jumping to conclusions too fast.

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Jessa Claire is a registered healthcare provider. Music lover. Daydreamer. Thalassophile. Foodie. A hardworking Capricorn. Most days, an incurable empath. An old soul. Down-to-earth. Vibrant. When she's not writing, she can be seen relaxing with headphones on or engrossed in her favorite fan fiction book.