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100 Deep Questions To Ask A Guy: Know Him Better
- Yaw Amoateng
- 2 days ago
- 4 min read
What is in this article?
You’ve met this wonderful guy. The conversations flow easily, and there’s definitely a connection, but something tells you there’s more beneath the surface. You can sense there are layers he hasn’t yet shared, pieces of his story still untold.
If you want to move beyond casual talk and truly understand who he is, his values, past experiences, fears, dreams, and what makes him him, then asking the right questions is key. In this article, we’ll explore powerful and thoughtful questions to ask a guy to know him deeper and build a more meaningful connection.
100 Questions To Ask Him To Him Deeper
Here are 100 deep questions to ask a guy if you truly want to know who he is beyond the surface. These questions go beyond small talk, they’re designed to help you uncover his values, fears, dreams, past experiences, and how he really thinks about love, relationships, and life.
Emotional Maturity & Vulnerability
How do you usually handle conflict in your life?
What’s something you’ve learned from a past heartbreak?
How do you show love to someone you care about?
What does vulnerability mean to you?
When was the last time you cried, and why?
How do you react when someone challenges your opinion?
What makes you feel emotionally safe with someone?
Do you find it easy or difficult to express your feelings?
What’s something you’re still healing from?
How do you deal with stress or feeling overwhelmed?
Understanding His Mindset
Do you consider yourself more of a thinker or a sharer?
What’s something people misunderstand about you?
What makes you feel misunderstood in relationships?
What beliefs do you hold about love and relationships?
What do you wish more women understood about men?
What’s your idea of a mature man?
Do you believe men and women handle emotions differently?
What makes you feel respected?
How do you usually deal with rejection?
Have you ever struggled with self-worth?
Purpose & Direction
What’s your biggest passion in life?
Do you feel like you’re living your purpose?
What motivates you to keep going on tough days?
What kind of legacy do you want to leave behind?
What does success mean to you?
Do you believe money can bring happiness or peace?
What role does work play in your life?
Have you ever felt lost or directionless?
What’s a personal goal you're working toward right now?
Do you think a relationship should support individual goals?
Past Relationships & Experience
What did your last relationship teach you?
Have you ever been truly in love?
What ended your last serious relationship?
Have you ever been the one to walk away? Why?
What kind of partner brings out the best in you?
Do you believe in second chances?
What’s the most romantic thing you’ve ever done?
Do you still keep in touch with your exes?
How did your parents' relationship influence your own views?
What’s one red flag you’ve learned to never ignore?
Love, Trust, and Commitment
What does commitment mean to you?
Are you a “right now” or “long-term” type of guy?
Do you believe love is a choice or a feeling?
What makes you feel loved?
How do you rebuild trust when it’s broken?
Have you ever had a fear of commitment?
What makes a relationship worth fighting for?
What are your relationship dealbreakers?
How do you know when it’s time to let someone go?
What kind of emotional connection do you need from a partner?
Communication & Understanding
Do you prefer to talk things out immediately or take space?
What’s the best way for someone to communicate a need to you?
Have you ever struggled to ask for help or support?
How do you usually express anger or frustration?
Do you feel heard in most of your relationships?
What’s something you’re afraid to say but want someone to know?
How do you react when someone gives you honest feedback?
What’s something you wish you could say to your younger self?
Do you think men are taught to suppress emotions?
What’s the hardest truth you’ve had to accept?
Intimacy & Sex
What does a healthy sex life mean to you?
How do you feel about discussing sexual desires with a partner?
Do you think emotional intimacy is more important than physical?
How do you handle dry spells or low desire phases?
Have you ever felt judged for your fantasies or desires?
What helps you feel most connected during intimacy?
What’s something new you’d like to try with a partner?
How important is physical touch in your relationships?
Do you believe sex can fix a broken relationship?
How do you initiate sex when you’re in the mood?
Growth, Change & Self-Awareness
What’s something you’re actively working on within yourself?
Have you ever been in therapy or considered it?
What’s your biggest fear about relationships?
What does personal growth look like to you?
Do you reflect on your past to learn from it?
What triggers you and how do you manage it?
What’s one habit you’d like to break?
How do you define emotional intelligence?
What does self-care look like in your life?
How do you handle change?
Connection, Compatibility & Partnership
What qualities make someone a great partner?
Do you believe two people should grow together or separately?
How important is compatibility in a relationship?
What does partnership mean to you?
How do you resolve disagreements with a partner?
Do you believe love can overcome anything?
What kind of emotional support do you need?
How do you show appreciation to someone you love?
Do you believe in traditional gender roles in relationships?
What does “being on the same page” mean to you?
Fears, Desires & Dreams
What’s your biggest fear in life?
What’s a dream you’ve never told anyone?
What’s one thing you hope never changes about you?
What would you do if you had no fear?
What’s something you secretly wish for in a partner?
Do you ever feel like you’re not enough?
What does emotional safety look like to you?
What’s your biggest hope for your future relationship?
What makes life feel meaningful to you?
What would a “dream relationship” look like for you?
