Questions to Ask Your Boyfriend to Test His Loyalty
Thoughtful questions to assess your boyfriend's commitment, trustworthiness, and dedication to your relationship without being accusatory.
1How do you define loyalty in a relationship?
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How do you define loyalty in a relationship?
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Why this works
Reveals his values and whether his definition aligns with yours before evaluating his actions.
2What would you do if someone flirted with you while we're together?
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What would you do if someone flirted with you while we're together?
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Why this works
Shows how he handles temptation and whether he sets appropriate boundaries.
3Have you ever cheated in a past relationship, and what did you learn from it?
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Have you ever cheated in a past relationship, and what did you learn from it?
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Why this works
Past behavior can indicate patterns, but his reflection shows growth and self-awareness.
4Who do you talk to when you're upset with me?
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Who do you talk to when you're upset with me?
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Why this works
Reveals whether he processes conflicts appropriately or seeks validation from inappropriate sources.
5Would you tell me if you developed feelings for someone else?
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Would you tell me if you developed feelings for someone else?
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Why this works
Tests his commitment to honesty even in difficult, uncomfortable situations.
6What boundaries do you think are important in our relationship?
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What boundaries do you think are important in our relationship?
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Why this works
Shows whether he's thought about protecting the relationship and respecting your connection.
7How would you want me to handle it if someone hit on me?
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How would you want me to handle it if someone hit on me?
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Why this works
Reveals his expectations for your behavior, which should mirror his own.
8Do you think it's okay to have close friendships with exes?
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Do you think it's okay to have close friendships with exes?
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Why this works
Clarifies his views on boundaries with past romantic partners.
9What's something you've done that you think shows your commitment to us?
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What's something you've done that you think shows your commitment to us?
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Why this works
Lets him demonstrate his loyalty through specific examples rather than general promises.
10If I needed to see your phone right now, would you be comfortable with that?
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If I needed to see your phone right now, would you be comfortable with that?
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Why this works
Tests transparency, though mutual trust shouldn't require constant phone checking.
11How do you handle attraction to other people while in a relationship?
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How do you handle attraction to other people while in a relationship?
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Why this works
Realistic acknowledgment that attraction happens; what matters is how he manages it.
12What would make you consider ending our relationship?
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What would make you consider ending our relationship?
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Why this works
Identifies his deal-breakers and shows what he values most in the partnership.
13Have you ever lied to me about something important?
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Have you ever lied to me about something important?
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Why this works
Creates space for honesty about past deceptions and willingness to come clean.
14Where do you see us in five years?
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Where do you see us in five years?
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Why this works
Shows whether he's thinking long-term or just going through the motions.
15How would you react if one of your friends disrespected me?
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How would you react if one of your friends disrespected me?
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Why this works
Tests whether he'll defend you and prioritize your relationship over friendships.
16What's your biggest fear about our relationship?
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What's your biggest fear about our relationship?
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Why this works
Vulnerability about fears often reveals what he values most and wants to protect.
17Do you tell your friends details about our relationship or intimate life?
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Do you tell your friends details about our relationship or intimate life?
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Why this works
Shows whether he respects your privacy and keeps your relationship sacred.
18If things got really hard between us, would you work through it or give up?
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If things got really hard between us, would you work through it or give up?
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Why this works
Reveals his commitment level when faced with challenges versus fair-weather loyalty.
19What does being faithful mean to you beyond just physical?
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What does being faithful mean to you beyond just physical?
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Why this works
Explores emotional fidelity and whether he understands loyalty encompasses more than avoiding cheating.
20Is there anything you're keeping from me that you think I should know?
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Is there anything you're keeping from me that you think I should know?
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Why this works
Opens the door for honesty and shows whether he's hiding things that affect the relationship.
Best Practices for Assessing Loyalty
Expert tips and techniques for getting the most out of these questions.
Best Practices
Ask with Curiosity, Not Accusation
Frame questions as wanting to understand him better, not as interrogation or trap-setting.
Watch Actions, Not Just Words
Anyone can say the right things. Pay attention to whether his behavior matches his answers.
Be Honest About Your Own Boundaries
Share your definition of loyalty and expectations so he knows what you need.
Trust Your Intuition
If something feels off despite good answers, don't dismiss your gut feeling.
Conversation Sequences
The Values Alignment Sequence
The Hypothetical Test Sequence
The Future Commitment Sequence
Common Pitfalls
Don't Use Questions as Weapons
These aren't meant to catch him in lies or create conflict. Use them to build understanding.
Don't Ignore Red Flags
If his answers raise concerns, don't rationalize them away. Take them seriously.
Don't Test Constantly
Healthy relationships are built on trust, not constant testing. Use these conversations sparingly.
Don't Compare Him to Exes
Judge him on his own character and actions, not against past partners.