20 Questions

Questions to Ask Cheaters

Difficult but necessary questions to help you understand infidelity, process betrayal, and make informed decisions about your relationship after cheating.

1

Why did you cheat, and what led to this decision?

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Why this works

Helps you understand the underlying reasons for the infidelity, which is crucial for determining if the relationship can be repaired and what changes are needed.

2

How long has this been going on, and when did it start?

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Why this works

Provides clarity on the scope and duration of the betrayal, helping you understand the full extent of the deception and plan your response accordingly.

3

What was your relationship with this person, and how did it develop?

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Why this works

Helps you understand the nature of the affair and whether it was emotional, physical, or both, which affects how you process the betrayal.

4

Did you ever consider ending the affair, and what stopped you?

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Why this works

Reveals their level of awareness about the wrongness of their actions and whether they had opportunities to stop but chose not to.

5

How do you feel about what you've done, and do you have any regrets?

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Why this works

Helps you assess their level of remorse and whether they truly understand the impact of their actions on you and the relationship.

6

What did you tell yourself to justify cheating, and how did you rationalize it?

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Why this works

Provides insight into their thought process and whether they have the self-awareness to understand their own justifications and rationalizations.

7

Did you ever think about how this would affect me, and what did you think would happen?

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Why this works

Reveals their level of consideration for your feelings and whether they thought about the consequences of their actions.

8

What do you want to happen now, and what are your intentions for the future?

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Why this works

Helps you understand their current feelings and intentions, which is crucial for deciding whether to attempt reconciliation or end the relationship.

9

Are you willing to end all contact with this person, and what steps will you take?

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Why this works

Tests their commitment to ending the affair and shows whether they're willing to take concrete steps to rebuild trust.

10

What do you think needs to change in our relationship, and what are you willing to do differently?

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Why this works

Helps you understand their perspective on the relationship problems and whether they're willing to take responsibility for their part in the issues.

11

How do you plan to rebuild trust, and what specific actions will you take?

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Why this works

Tests their understanding of what's needed for reconciliation and whether they have a realistic plan for rebuilding trust.

12

What support do you need to avoid cheating again, and what are you willing to do to get it?

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Why this works

Reveals their commitment to change and whether they're willing to seek help to address the underlying issues that led to the infidelity.

13

How do you think this has affected me, and what do you think I'm feeling right now?

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Why this works

Tests their empathy and understanding of the impact of their actions on you, which is crucial for genuine remorse and change.

14

What would you do differently if you could go back in time, and what have you learned?

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Why this works

Helps you assess their level of self-reflection and whether they've gained insight into their behavior and its consequences.

15

Are you willing to be completely transparent about your activities and whereabouts?

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Why this works

Tests their willingness to be accountable and transparent, which is essential for rebuilding trust and preventing future deception.

16

What do you think our relationship was missing that led you to seek it elsewhere?

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Why this works

Helps you understand their perspective on the relationship problems and whether they're willing to work on addressing these issues together.

17

How do you plan to handle temptation in the future, and what strategies will you use?

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Why this works

Tests their understanding of the need for boundaries and whether they have a plan for avoiding future infidelity.

18

What do you think I need to know to make an informed decision about our future?

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Why this works

Gives them an opportunity to share any additional information they think is important for your decision-making process.

19

How do you plan to make amends, and what are you willing to do to repair the damage?

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Why this works

Tests their understanding of the need for amends and whether they're willing to take concrete steps to repair the relationship.

20

What do you think our relationship needs to survive this, and are you committed to doing the work?

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Why this works

Helps you understand their commitment to the relationship and whether they're willing to put in the effort needed for reconciliation.

Navigating Conversations About Infidelity

Expert tips and techniques for getting the most out of these questions.

Best Practices

Take Time to Process

Don't rush into conversations about the infidelity. Take time to process your emotions and think about what you need to know.

Set Boundaries

Establish clear boundaries for the conversation and don't allow yourself to be manipulated or gaslighted. You have the right to ask difficult questions.

Seek Support

Don't go through this alone. Seek support from trusted friends, family, or a therapist who can help you process your emotions and make decisions.

Question Sequences

The Understanding Seeker

1
Why did you cheat, and what led to this decision?
2
How long has this been going on?
3
What was your relationship with this person?
4
Did you ever consider ending the affair?

The Future Planner

1
What do you want to happen now?
2
Are you willing to end all contact with this person?
3
How do you plan to rebuild trust?
4
What do you think our relationship needs to survive this?

Common Pitfalls

Don't Accept Blame

Don't let them blame you for their infidelity. While relationship problems may exist, cheating is always a choice, and you are not responsible for their decision.

Avoid Rushing Decisions

Don't make hasty decisions about the relationship. Take time to process your emotions and think about what you need for your own well-being.

Don't Ignore Red Flags

If they're not taking responsibility, showing remorse, or willing to make changes, these are red flags that the relationship may not be salvageable.

Conversation Templates

The Truth Seeker

1
Step 1: Start with: "Why did you cheat, and what led to this decision?"
2
Step 2: Follow with: "How long has this been going on?"
3
Step 3: Deepen with: "What was your relationship with this person?"
4
Step 4: Complete with: "Did you ever consider ending the affair?"

The Future Builder

1
Step 1: Begin with: "What do you want to happen now?"
2
Step 2: Explore with: "Are you willing to end all contact with this person?"
3
Step 3: Investigate with: "How do you plan to rebuild trust?"
4
Step 4: Decide with: "What do you think our relationship needs to survive this?"

Further Reading

"After the Affair" by Janis Abrahms Spring
"Not Just Friends" by Shirley Glass
"The State of Affairs" by Esther Perel

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