17 Questions to Ask a Guy (Know His Intentions)

Key Takeaways:

• Discuss long-term goals early
• Learn his values for deeper insight
• Understand his conflict resolution style
• Address sensitive topics thoughtfully
• Gauge compatibility through open dialogue

Ever wondered what goes on in a guy's mind when you're getting to know each other? Maybe you've felt that gut-wrenching uncertainty, wondering if he's in it for the long haul or just enjoying a casual fling. Trust me, we've all been there. Our instincts tell us to protect ourselves while trying to build something meaningful. But how do you decode someone's true intentions without sounding like you're giving them the third degree?

Communication experts emphasize the power of asking the right questions. As Dr. John Gottman, renowned for his work on relationships, says, “What makes relationships work is surprisingly simple: understanding your partner.” So let's dive into these essential questions that can help you get to the heart of his intentions while building a deeper, more authentic connection.

17 questions to ask a guy to know his intentions

Let's face it: understanding a guy's true intentions can feel like deciphering a complex code. One moment he's all in, and the next, you're questioning what his words even mean. The key here is to approach conversations thoughtfully. Yes, that means asking the right questions, the kind that don't just scratch the surface but genuinely explore what's driving him. This doesn't mean interrogating him but rather creating space for an open, authentic exchange. Let's explore.

1. What are your long-term goals?

Long-term goals can reveal so much about a person. When you ask this question, pay attention not only to what he says but also to his excitement—or lack of it—when discussing the future. Maybe he dreams of traveling the world, or perhaps he's focused on climbing the corporate ladder. Either way, knowing his aspirations gives you insight into whether your paths might align or if they're destined to diverge.

Psychologically, a person's vision for the future can indicate their level of maturity and readiness for commitment. If he struggles to articulate any goals, he might not be ready for something serious. On the flip side, hearing him speak passionately about his dreams could reveal that he's someone with a plan—and hopefully, room in it for a significant other.

2. What do you value most in a relationship?

Values are the bedrock of any strong connection. Maybe he values honesty above all else or places a high priority on quality time. Asking about his core relationship values helps you understand how he views partnerships and whether those views are compatible with yours.

Think about this: If you deeply value communication but he brushes off its importance, there might be a disconnect. Relationship therapist Esther Perel notes, “Our values guide our actions, and understanding them is crucial to relational alignment.” This question isn't about judging him; it's about clarity. When two people's values sync, the foundation becomes rock solid.

3. How do you handle conflict?

Every couple fights. The difference between thriving relationships and toxic ones often comes down to how conflicts get resolved. This question will help you understand his emotional toolkit. Does he lash out or shut down, or is he committed to finding solutions and moving forward?

Conflict resolution reveals emotional intelligence. Research by Dr. Gottman highlights that successful relationships thrive on repair attempts and the willingness to de-escalate tensions. If he acknowledges the importance of working through issues constructively, it's a sign of relational maturity. And if he admits he's still learning? That's okay too, as long as he's open to growth.

4. What's your perspective on commitment?

Commitment: it's a loaded word, and it means different things to different people. For some, commitment represents marriage and a lifelong partnership. For others, it's about emotional exclusivity. Asking about his view helps you understand what he envisions in a committed relationship.

Notice his body language when he answers. Does he look uneasy or speak confidently about the idea of a committed future? If he's upfront about wanting something casual, that's a red flag if you're seeking long-term love. And if he's enthusiastic about building a life together someday, well, you might just be on the same page.

5. What do you like to do in your free time?

Sometimes, it's the seemingly small questions that reveal a person's true essence. Asking what he enjoys in his free time can unveil his passions and the things that make him feel most alive. Maybe he loves hiking up rugged trails, losing himself in nature. Or perhaps he's more of a homebody who finds comfort in cozy movie nights and long books.

Discovering how he spends his time outside of responsibilities can also hint at your potential compatibility. If your ideal weekend involves adventuring across new cities, but he's happiest binge-watching TV shows, it's something to consider. However, differences aren't deal-breakers. What matters is how willing you both are to embrace each other's interests.

6. How do you see us in the future?

This one can feel nerve-wracking to ask, especially if the relationship is still budding. But understanding his vision of your future together is crucial. Listen carefully to his response. Does he mention you as part of his long-term plans, or does he speak about himself exclusively?

Sometimes, we hesitate to ask this question out of fear of sounding too eager. Yet, knowing if he sees a shared future allows you to decide if you're investing your time in the right place. A vague or evasive answer might indicate uncertainty. On the other hand, if he speaks with sincerity about building a life together, it's a sign that you might be aligned.

7. What are your family and friends like?

People often say that you can learn a lot about someone by observing the company they keep. Asking about his family and friends gives you a glimpse into his world. What kind of relationships does he have with them? Are they supportive and close-knit, or does he prefer keeping a distance?

Family dynamics and friendships shape us more than we sometimes realize. If he talks lovingly about his mom or describes weekly get-togethers with friends, it shows a sense of community. If he's more reserved about his connections, it doesn't necessarily mean something negative, but it's an opening to discuss the role of relationships in his life.

8. How do you handle stressful situations?

We all experience stress. It's how we manage it that often defines our ability to maintain healthy relationships. When you ask this, don't just focus on his answer but how he feels about his approach to stress. Does he say he needs alone time to decompress, or does he prefer hashing things out with friends?

Psychologists often highlight the importance of stress management strategies. If he acknowledges areas where he's trying to improve, that's a good sign. None of us have it all figured out, but the willingness to handle pressure thoughtfully speaks volumes. You'll want to know whether his way of coping complements or clashes with yours.

9. What's your take on personal growth?

Personal growth isn't just a trendy buzzword; it's about striving to become the best version of yourself. When you ask him this question, listen for signs of self-awareness. Does he believe in continual learning and self-improvement, or does he feel content coasting through life as is?

Someone invested in personal growth is often open to evolving and embracing change. Whether it's through reading, therapy, or taking up new hobbies, a growth-oriented mindset can make a relationship more dynamic. If he values personal development, chances are he'll also support you in your journey. This could be a strong indication that he's willing to put in the work for a thriving partnership.

10. What's your perspective on finances?

Talking about money can be awkward, but it's necessary. A person's financial philosophy can significantly impact a relationship. Is he a spender, a saver, or somewhere in between? Does he have a strategic plan for his financial future or prefer living spontaneously without much planning?

Money conversations are less about exact numbers and more about attitudes and compatibility. If he's adamant about joint accounts while you're fiercely independent with your finances, you may need to have deeper discussions down the line. Financial stress is one of the most common sources of relationship conflict. Being on the same page—or at least open to compromise—can make a world of difference.

11. How do you define trust and honesty?

Trust and honesty form the core of any meaningful relationship. This question might seem obvious, but his answer can give you profound insights into how he operates in a partnership. Maybe for him, trust is built slowly, brick by brick. Or perhaps he's someone who gives it freely until it's broken.

Ask for examples of what trust means to him. Does he equate honesty with brutal, unfiltered truth, or does he believe in sparing feelings sometimes? Trust is nuanced, and his perspective will either reassure you or raise some red flags. Ultimately, understanding his beliefs about honesty and loyalty sets expectations and minimizes misunderstandings.

12. What's your approach to intimacy?

Let's talk about intimacy. This subject is about more than just physical connection. It's about emotional closeness and vulnerability. When you ask this question, you're exploring what makes him feel bonded in a relationship. Is intimacy something he prioritizes or struggles to express?

Discussing intimacy openly can foster a deeper sense of understanding. If he feels uncomfortable or dismisses its importance, it might signal difficulty in building a truly connected partnership. On the flip side, if he's eager to talk about creating an intimate space—emotionally and physically—it shows that he's in touch with what makes a relationship thrive.

13. How do you prioritize work-life balance?

In today's hustle culture, work-life balance can be a serious challenge. Understanding his stance on this can reveal a lot about what daily life with him might look like. Does he believe in shutting off work at a reasonable hour to spend quality time together, or is he glued to his laptop even at dinner?

Healthy work-life boundaries can strengthen a relationship. If he's career-driven but also carves out time for self-care and loved ones, that's a great sign. But if work dominates his life and leaves little room for a relationship, it could be a warning sign, especially if you value shared time and experiences.

14. What are your past relationship experiences?

Asking about past relationships isn't about being nosy or digging up skeletons. It's about understanding what he's learned and how he's grown. Maybe he had a long-term partner who taught him the importance of communication. Or perhaps he's been through heartbreak that made him wary but wiser.

Talking about exes and previous dynamics can be revealing. Does he speak respectfully about his past partners or blame them entirely for failed relationships? His narrative will show you whether he's taken accountability and learned from his experiences. Growth often comes from reflecting on the past, and the way he shares his stories can give you insight into his emotional readiness.

15. How do you apologize when you're wrong?

Let's be real: apologizing when you're wrong isn't always easy. It requires humility and vulnerability. This question gives you a window into his accountability. Does he own up to his mistakes, or does he brush them off, hoping they'll disappear on their own?

A sincere apology includes acknowledging the impact of one's actions, expressing genuine remorse, and making amends. If he talks about how he strives to make things right, it's a sign of emotional maturity. On the other hand, if he gets defensive or struggles to admit wrongdoing, it could spell trouble for future disagreements. Healthy conflict resolution often starts with a heartfelt, authentic apology.

16. What's your definition of love?

Ah, love. It's one of those words that means something different to everyone. Asking for his definition can reveal how he thinks, feels, and acts in a relationship. Some may describe love as unconditional support, while others highlight partnership and shared values.

Is love, to him, about grand romantic gestures or the quiet, everyday moments? Does he believe love grows over time or that it strikes instantly, like lightning? His perspective matters, especially if you're trying to understand if you both want the same kind of bond. Knowing how he defines and demonstrates love helps set the tone for your relationship journey.

Commonly asked questions

We've covered a lot, but you might still have lingering concerns. Here are some common questions that come up when trying to gauge a guy's intentions. Let's break them down for more clarity.

How soon should I ask about a guy's intentions?

The timing of this conversation depends on how your connection unfolds. Typically, it's best to bring up intentions after a few meaningful dates, once you feel comfortable and a level of trust is forming. However, if the relationship seems to be progressing rapidly, don't hesitate to address your concerns sooner.

Remember, it's not about pressuring him but understanding where you both stand. The sooner you know his intentions, the sooner you can make decisions that are right for you.

What if he avoids answering questions about his intentions?

It's normal to feel uneasy if he dodges your questions. Avoidance can sometimes signal uncertainty or a reluctance to commit. If he repeatedly sidesteps discussions about the future or his goals, take it as valuable information. You deserve clarity.

Approach the situation with grace but stay firm about your needs. If he's unwilling to be transparent, it might be time to reconsider whether the relationship aligns with what you're looking for. Your peace of mind matters.

Are these questions suitable for casual dating?

It depends on the nature of your casual dating. If you're just having fun and keeping things light, some of these questions might feel out of place or too intense. However, if your version of casual dating involves genuine emotional connection and you're hoping for some form of exclusivity, it's okay to ask a few of these.

Be mindful of the energy in your conversations. Asking about trust and values, for instance, can help you understand if the two of you are on the same page, even if it's a short-term situation. Keep it conversational and avoid making it feel like an interview. A natural flow keeps things comfortable and engaging.

Should I ask about past relationships in early conversations?

Bringing up past relationships too soon can be a double-edged sword. On one hand, understanding his relationship history gives you a glimpse into what shaped him and how he's evolved. On the other hand, diving in too early could make things feel heavy before a strong foundation is built.

If you decide to ask, frame it in a way that feels supportive, not probing. Instead of asking for every detail, you might say, “Have your past relationships taught you anything about what you want for the future?” This way, you keep the focus forward-looking and avoid making him uncomfortable.

How do I bring up sensitive topics without making him uncomfortable?

Bringing up sensitive subjects can feel like walking a tightrope, but it doesn't have to be daunting. Timing and tone matter. Choose a relaxed setting where both of you feel safe and at ease. You might start by using “I” statements, which focus on your feelings and experiences rather than placing blame or making assumptions.

For example, you can say, “I'd love to understand more about your thoughts on…” instead of, “Why don't you ever talk about…” This invites dialogue rather than defensiveness. Empathy and active listening are key. Being considerate of his comfort doesn't mean you should tiptoe around your needs. It's all about balance.

Summing up

Getting to the bottom of a guy's intentions can feel overwhelming, but open and thoughtful communication goes a long way. These questions are designed to foster deeper understanding and connection, helping you make informed choices about your relationship. Remember, it's perfectly okay to seek clarity and set boundaries that work for you.

Relationships thrive on mutual respect and open dialogue. Don't be afraid to ask for what you need, but also remain receptive to his answers, even if they don't align with what you hoped to hear. It's all about finding the right fit, one conversation at a time.

Recommended Resources

• The Seven Principles for Making Marriage Work by Dr. John Gottman
• Mating in Captivity by Esther Perel
• Attached: The New Science of Adult Attachment by Dr. Amir Levine and Rachel Heller