Flirty Questions to Ask Your Ex Boyfriend
Playful and flirty questions to reconnect with your ex-boyfriend, test the waters, and potentially rekindle the spark between you.
1Do you ever think about what we had, or am I the only one who still remembers those moments?
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Do you ever think about what we had, or am I the only one who still remembers those moments?
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Why this works
Opens the door to discussing your past relationship in a way that's both nostalgic and potentially romantic, while gauging his current feelings.
2What's the one thing about me that you miss the most?
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What's the one thing about me that you miss the most?
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Why this works
Encourages him to reflect on your positive qualities and creates an opportunity for him to express what he valued about you.
3If you could change one thing about how our relationship ended, what would it be?
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If you could change one thing about how our relationship ended, what would it be?
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Why this works
Shows you're thinking about the past constructively and gives him a chance to express any regrets or what-ifs he might have.
4Do you ever wonder what would have happened if we had tried harder to make it work?
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Do you ever wonder what would have happened if we had tried harder to make it work?
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Why this works
Explores the possibility of reconciliation in a subtle way and helps you understand if he's open to the idea of trying again.
5What's the first thing that comes to mind when you think of me?
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What's the first thing that comes to mind when you think of me?
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Why this works
Gives you insight into his current perception of you and whether his memories are positive or negative.
6If we could go back to any moment in our relationship, which one would you choose?
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If we could go back to any moment in our relationship, which one would you choose?
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Why this works
Creates a shared nostalgic experience and helps you understand what moments he valued most in your relationship.
7Do you think we've both grown enough to make it work this time?
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Do you think we've both grown enough to make it work this time?
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Why this works
Acknowledges that people change and mature, and explores whether the issues that led to the breakup might be resolved now.
8What's something you never told me when we were together that you wish you had?
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What's something you never told me when we were together that you wish you had?
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Why this works
Creates intimacy and vulnerability, and gives him a chance to share something meaningful that he might have held back before.
9If I asked you to give us another chance, what would you say?
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If I asked you to give us another chance, what would you say?
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Why this works
Directly tests his willingness to reconcile while giving him the opportunity to express his current feelings about the relationship.
10What's the most attractive thing about me that you still remember?
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What's the most attractive thing about me that you still remember?
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Why this works
Flirty and direct, this question helps you understand what he found appealing about you and whether he still sees you in that light.
11Do you ever compare other people to me, or am I just a distant memory now?
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Do you ever compare other people to me, or am I just a distant memory now?
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Why this works
Helps you understand his current perspective on you and whether you still hold a special place in his thoughts.
12What would you do differently if we started over?
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What would you do differently if we started over?
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Why this works
Shows you're thinking about the future and gives him a chance to reflect on what he learned from the relationship.
13Do you think we were meant to be together, or was our relationship just a learning experience?
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Do you think we were meant to be together, or was our relationship just a learning experience?
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Why this works
Explores his beliefs about the relationship's significance and whether he sees it as something that could be rekindled.
14What's the one thing you wish you could tell me right now?
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What's the one thing you wish you could tell me right now?
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Why this works
Creates an opportunity for him to share something important or meaningful that he might not have said before.
15If we could spend one perfect day together, what would we do?
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If we could spend one perfect day together, what would we do?
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Why this works
Playful and romantic, this question helps you understand his ideal version of your relationship and creates a shared fantasy.
16Do you ever dream about me, or am I just someone from your past now?
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Do you ever dream about me, or am I just someone from your past now?
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Why this works
Intimate and personal, this question explores whether you still occupy his thoughts and dreams.
17What's the biggest mistake you think we both made in our relationship?
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What's the biggest mistake you think we both made in our relationship?
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Why this works
Shows you're both reflective and willing to take responsibility, which is important for any potential reconciliation.
18If you could have one more chance to kiss me, would you take it?
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If you could have one more chance to kiss me, would you take it?
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Why this works
Directly flirty and romantic, this question tests his physical attraction and willingness to be intimate with you again.
19What's something you learned about yourself after our breakup that you wish you had known when we were together?
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What's something you learned about yourself after our breakup that you wish you had known when we were together?
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Why this works
Encourages him to share personal growth and gives you insight into how he's changed since the relationship ended.
20Do you think we could be friends with benefits, or would that be too complicated?
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Do you think we could be friends with benefits, or would that be too complicated?
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Why this works
Tests the waters for a casual relationship while acknowledging the complexity of your history together.
Navigating Ex-Boyfriend Reconnection
Expert tips and techniques for getting the most out of these questions.
Best Practices
Gauge His Interest First
Start with subtle questions to test the waters before diving into more direct or intimate topics. Pay attention to his responses and body language.
Be Honest About Your Intentions
If you're looking to reconnect romantically, be clear about your intentions while being respectful of his current situation and feelings.
Respect His Boundaries
If he's not interested in reconnecting, respect his decision and don't push. Focus on building a healthy friendship or moving on.
Question Sequences
The Nostalgic Reconnection Sequence
The Future Possibility Sequence
Common Pitfalls
Don't Rush the Process
Take time to rebuild trust and connection before jumping into romantic territory. Rushing can lead to the same problems that ended the relationship.
Avoid Bringing Up Past Hurts
Focus on positive memories and future possibilities rather than dwelling on what went wrong. This creates a more positive foundation for reconnection.
Don't Ignore Red Flags
If he's not showing interest or is being disrespectful, don't pursue the reconnection. Your self-respect is more important than rekindling the relationship.