20 Trick Questions to Catch a Cheater: Outsmart Them!

suspicious man

It’s a tough pill to swallow, isn’t it? When trust, that once unshakeable bedrock of your relationship, starts to crumble under the whispers of doubt. As daunting as it may seem, the reality reflects it – 21% of Americans confessed to infidelity in 2021.

Our guide isn’t just about throwing a net of trick questions to catch a cheater. It’s about equipping you with tools that unveil the truth and a secret weapon that solidifies your doubts into proof. Ready to dive in? Let’s go.

1. I was thinking, would you be comfortable if we did everything together?

Seems like an innocent proposal, doesn’t it? But it’s one of trick questions to ask your boyfriend to see if he’s cheating. Their response might hint at their comfort level around you.

2. Did you know my friend Sarah works at that new café downtown? The one you started visiting often?

A perfect way to observe his reactions. If he’s visiting the café because of another person, his expressions might give him away.

3. Why don’t we share our social media accounts? I think it could be fun to post as a couple.

Not just a casual proposal but also a tricky question to ask your boyfriend. Will he agree enthusiastically or hesitate? His response might be more revealing than he realizes.

4. What do you think about family therapy?

If your partner sticks to the topic and is open to it, he’s willing to take your relationship seriously. Cheater or not, his attitude toward therapy could give you some valuable insights.

5. Why are we not as intimate as we used to be? Are my cuddles not enough anymore?

Start an innocent conversation about the topic. Your partner’s reactions might reveal if they’re losing interest or just stressed out.

6. So, Emma wants to try an open relationship with Mark. She thinks it might add some spice to their relationship. Isn’t that just crazy?

You’re discussing someone’s relationship, but this is a tricky question to ask your boyfriend. His take on open relationships could indicate how he feels about yours. 

7. My old college friend Sam is in town. He wants to hang out tomorrow night. You wouldn’t mind, would you?

If your partner is cheating, you will probably get an angry reaction. Guilt can make people act out in strange ways. If he is not, then you will get a more calm response. 

8. If there was one thing you could change about our relationship, what would it be?

On the surface, it’s one of the simple questions to ask a cheater. But it can provoke them into Oscar-worthy performances. They can unexpectedly confess their infidelity or point at your flaws in the relationship.

9. Why do you think we argue more often these days?

You’re just looking to understand the change, but a cheater might consider it an accusation. Instead of validating your feelings, they’ll either go on the defensive or come up with a flimsy excuse. 


10. This podcast I listen to says that men who buy gifts unexpectedly might feel guilty about something. Weird, isn’t it?

What seems like an off-hand comment on a random podcast episode is, in fact, an indirect tricky question to ask your boyfriend. Watch for signs of discomfort or over-compensating when you ask this one.

11. You seem distracted lately. Is there something on your mind?

Express honest concern. If they have nothing to hide, you will get a straight answer. A cheater will brush off the question or make up a lie. 

12. “I can’t remember, what did you say you were doing on Thursday morning?

Playing forgetful, clever! You’re throwing him a lifeline, offering him a chance to stick to his story or get caught in a lie. 

13. You’ve been less interested in me in bed. Are you researching a new sleeping technique?

This isn’t just a funny comment; it’s a tricky question to ask your boyfriend. If he’s cheating, there might be a hint of distress in his response.

14. This new bracelet of yours is pretty stylish. Can I try it on?

If you’re lucky enough to find a gift you don’t remember buying, this could be a crucial clue. Ask to try it on and see what reaction you get. A cheater might be embarrassed if he knows where the gift came from!

15. Do you believe people can change after making a serious mistake in a relationship?

Engaging in meaningful conversations comes naturally in a committed relationship, but cheaters may be uncomfortable discussing imaginary situations. If they respond quickly or defensively, that’s likely a bad sign.

16. I’ve got a little confession to make, but first, is there anything you’d like to tell me?

Hidden behind the façade of confession, it’s one of those deep questions to ask a cheating boyfriend. He may hesitate to answer or come up with an excuse why he can’t talk about it. 

17. I got a wrong number call for a ‘Natalie.’ Is that your old friend?

A random name drop can catch anyone off guard, especially if that’s not just an ‘old friend.’ Use similar conversation starters as clever trick questions to catch a cheater.

18. How about we go on more spontaneous dates?

To find out if he’s cheating, look for a response that hints at him being busy or having other plans. Creating a consistent routine is something people who cheat often tend to do. If your partner seems to avoid spontaneity, it might be a warning sign.

19. Do you think little white lies can harm a relationship?

Play it cool and use this as an opportunity to get a reaction out of them. They might be caught off guard to hear you bring up the subject of honesty in a relationship.

20. I can’t find my phone, could I use yours to call it?”

Yes, this is a tricky question to ask your boyfriend wrapped in a common scenario. He will turn your house upside down to bring your phone instead of handing you his device.

How to Catch a Cheater Red-Handed?

You’ve asked open-ended questions about cheating, and they’ve stirred some doubts. Now, you need more than just words. You need undeniable proof. How about we introduce you to your new secret weapon – Spynger, the trusted app to catch a cheater.


Spynger dives deeper, reaching places trick questions can’t. Think of it as a private investigator in your pocket. The level of detail and accuracy Spynger provides will leave your cheating spouse speechless.

Spynger’s Features 

Spynger features

The deep questions to ask a cheating boyfriend have given you a starting point, but Spynger takes you to the finish line. Here’s what you can check:

  • Call Logs and Text Messages: Who’s he calling late into the night? Spynger has got your back, from call logs to the content of text messages.
  • Social Media Monitoring: From cryptic Facebook posts to late-night Instagram DMs, Spynger reveals it all. 
  • GPS Location Tracker: Get real-time tracking along with the history of your partner’s movements. 
  • Media Access: Photos or videos,  Spynger will provide you with direct access. You might find more than just harmless selfies.
  • Browsing History: The internet has a vast array of secrets. Spynger uncovers the ones your partner is hiding.
  • Keylogger: Capture every keystroke, from search engine queries to deleted messages, even passwords.
  • Hidden Mode: Instant access to photos, videos, and voice notes. Who knows what you’ll find?

How to Install Spynger 

When it comes to ways how to ask your partner if they are cheating, solid proof is the best strategy. Get it in 3 steps with Spynger:

Step 1: Create Your Account

Create account

Just a few taps, and you have your own Spynger account. Simple and fast, you’re on your way to discovering the truth.

Step 2: Choose the Target Device Type

Choose device

Whether your partner uses Android or iOS, Spynger has got you covered. Select the platform of the device you wish to monitor.

Step 3: Get Your Answers

sad woman

All it takes is a login to your control panel, and their activity is right before your eyes. Clear as day. It’s time to uncover the truth.

Questions to Ask After Infidelity 

woman got cheated on

The truth’s out in the open, and it’s time for clarity. Here are 10 questions to ask your unfaithful spouse aimed at helping you understand what’s happened and move forward.

1. What was the turning point that led you to cheat?

One of the first deep questions to ask a cheating boyfriend or girlfriend is understanding what made them betray your trust. It unravels the circumstances that shifted their perspective or decision-making process. 

2. Did you think about the consequences?

Now, this isn’t as simple as it sounds. It’s important to understand that consequences don’t just involve the other person—it also involves you. Ask your partner if they ever thought of how their actions would affect you and your relationship.

3. Why didn’t you end our relationship before starting another?

Heartbreaking but crucial, tough questions to ask after infidelity involve understanding why they didn’t give you the closure you deserved before they started a new chapter with someone else. Possible answers might include fear of confrontation, guilt, or the desire to have someone else fill the void they felt in your relationship.

4. What do you think would have happened if I had found out another way?

This question forces them to think about the consequences of their actions—and how they would have played out had you found out in a different way. This can help both of you understand what needs to be done moving forward in order to rebuild trust.

5. Have you cut off all contact with the other person?

This is among the essential 10 questions to ask your unfaithful boyfriend. It is about setting boundaries, about ensuring they’ve severed ties with the third person, which is the first step towards mending your relationship.

6. Do you feel any remorse for your actions?

Unmasking true feelings is as important as understanding the facts. Your partner must feel remorse to move forward, and their feelings (or lack thereof) should be addressed before working on rebuilding the relationship.

7. How would we both rebuild trust going forward?

It’s confronting a cheating boyfriend head-on, asking for specifics about how you can do better to move past the hurt. It involves getting honest and open, discussing expectations, understanding boundaries, and taking action to keep them in place.

8. What would be different this time around?

This is a question that requires reflection and honesty from both sides. It’s important to talk about underlying issues, get into the root causes of the cheating and be open to making changes in yourself, your partner, or both. 

9. How can you assure me this will never happen again?

Among the 10 questions to ask your unfaithful spouse, this is about commitment and change. It’s about them giving you a solid promise that they’ve learned from their mistakes.

10. Do we need family or couples counseling?

The last question to ask, perhaps one of the most important, is whether counseling could help you both get back on track. Couples counseling can be a powerful tool in repairing broken trust, and it may be necessary for your relationship to move forward with integrity. 


Navigating through trick questions to catch a cheater is all about subtly seeking the truth. You don’t resort to extreme measures but play mind games to make them drop their guard. 

Subtle questioning alone isn’t always enough, though. You need solid proof. That’s where Spynger comes in. From call logs to location history, Spynger gives you the evidence to back up your hunches.

With your evidence in hand, you’re ready to start the conversation. Stay calm, ask your questions, and handle the truth with grace. You’re not just uncovering deceit – you’re also shaping the future of your relationship.

Patrice Sol is an esteemed author specializing in the art of catching cheaters and unmasking hidden truths. Leveraging her extensive experience as a private investigator and keen insights into human psychology, Patrice has honed her skills in unraveling complex webs of lies.

  • Some of these questions are genius! But I hope I never have to use them. I walked away from a toxic relationship, so it’s painful to think about cheating.

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