16 deep questions to ask a cheating boyfriend

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It’s every woman’s nightmare: a cheating boyfriend. 

If you’ve been cheated on you may be in disbelief and are likely feeling angry, sad, and confused. 

You want answers, and you want them now. 

Here are some questions to ask your boyfriend that go far beyond the basics and get at his deeper motivation for cheating. 

1) “Why did you do it?”

First of all, you want to know why he cheated on you. 

So ask.

I’m not going to pretend he’ll tell the truth or the whole truth here, but this gives you the chance to see his initial reaction. 

It’s also likely the very first question on your mind as you feel the rage and shame of a man you love treating you this way. 

So, why did he do it?

What does he say? 

He’s likely to say the same thing that most cheating boyfriends say:

“It meant nothing, I swear.”

If he says this, you have a right to be even angrier. What it did or didn’t mean isn’t really the question. The question is his motivation. 

And if he dodges it by claiming it was nothing in the first place then you have a right to be even more frustrated. 

Moving on to question two…

2) “Is this really the first time?”

The sad truth is that many guys are sadder about getting caught than about what they actually did. 

If he’s been busted for cheating on you, it might not be an isolated occurrence.

Ask him if this is the first time. If he realizes that you’re not joking around and that you will value his honesty more than his excuses, he may just tell you the truth. 

The truth might be that it really is the only time he’s cheated on you. 

Or it could be that it’s part of a much broader pattern of infidelity and disrespect. 

You deserve to know the full truth. 

You deserve the whole ugly picture of what’s going on and what’s been going on. 

At the very least he owes you that. 

3) “Why her?”

You’ll also want to know why he cheated on you with this woman. 

What was it about her that piqued his interest (or piqued other parts of his body)?

Why did he cheat on her?

If it was random, what does that say about his own discernment and taste? Are you just a random lay, too, who he’s stuck around with for longer than usual?

Saying it meant nothing or that he just got carried away isn’t the get-out-of-jail-free card he thinks it is.

It actually says a lot of negative things about his own ability to control himself and have strong motivations behind his decisions. 

If it did mean something or was part of a deeper affair, then you’ll have more to dig into about whether your own relationship has any future or hope. 

One of the things I really recommend here is to talk to a love coach. 

Relationship Hero is a site with accredited relationship coaches who are familiar in dealing with issues like cheating.

They can give you a lot more insight about your cheating boyfriend and what his answers mean when you’re asking him these questions. 

Click here to connect up with a love coach

4) “How did you meet and develop a connection?”

Before you can really know what to do about his cheating, you need to have a better picture of what happened. 

This is where you ask how he developed this connection and met her (or the various women) who he’s been cheating with.

How did it happen and what led to it?

His answer will tell you a lot about the context of the cheating and why it happened as well as the likelihood of it happening again. 

For example, if it was a coworker then the chances he’ll find another coworker in the future to cheat with are fairly high. 

If it was at a bar then it’s likely that he’s behaving recklessly when he’s out and about. 

If it’s a deeper connection that he formed in another way through his interests or other recreational activities he does then it could point to different paths in life that the two of you are taking. 

5) “What were you thinking?”

What was he thinking when he started to flirt with this girl and cheated, or when he allowed her to seduce him? 

The typical response to this will be that he “wasn’t thinking.”

This isn’t really an answer. 

You want to follow this up and find out why he wasn’t thinking…

What made him believe even for a split second that this wouldn’t backfire…

Would he have continued if he hadn’t gotten caught or you hadn’t realized he was cheating?

Most guys are going to give all the right answers or maybe even act like you’re traumatizing them with all these hard questions…

But the key is to look at the manner in which he responds:

Is he really remorseful and trying to tell you the truth?

Or does he look more like a guy being cross-examined and trying to wriggle out of it? 

Because if it’s option two then this is a guy you want to move on from. 

6) “Do you have feelings for her?”

Asking if he has feelings for her is a perfectly fair question and one that you deserve an answer to as soon as possible.

Whether or not he’s honest about this, it’s something you should ask about.

If he does have feelings for her and opens up about that, then this is generally the end of your relationship.

Sometimes it was really only about sex, which doesn’t necessarily make it better but does at least mean that it doesn’t have deeper layers. 

However, if there are more emotional layers to this then you deserve to know…

And he owes you to open up and be honest about that.

7) “Do you feel guilty?”

Your boyfriend’s mood has a lot to do with how he answers this kind of question.

Guilt is the natural reaction that somebody has when they harm or mistreat another person who did not deserve it. 

Presumably, he’s feeling very guilty, but making it explicit by asking him is a way to bring it out in the open. 

Just make sure he’s not using this an as excuse to get out of his actual blame in cheating on you. 

Him feeling sad or down about what he did is certainly likely to lower the mood and maybe even bring on some tears or stories of trauma from his life. 

But this isn’t really about him or how bad he feels. 

Him feeling guilty is how he should feel…

It’s natural and expected, so don’t feel bad that he feels guilty, he should!

8) “Were you actually single when you met me?”

A close friend of mine’s ex-boyfriend cheated on her last year and she was totally wrecked by it. 

Their two years together were basically exposed as a lie when she found out he’d had sex with at least three girls while in a relationship with her. 

What’s worse is that he’d told one of them he loved her and was basically dating my friend and the other woman at the same time. 

In fact, he had lied and told he woman he was cheating with that he was single when he met her. 

Be careful that this isn’t you.

Are you certain that your guy was actually single when he met you? Are you certain he stayed single while dating you and wasn’t simultaneously carrying on another relationship the whole time?

It sounds too brazen to be true but it absolutely happens. Make him spill the beans right on the spot. 

He’ll be too shocked to lie.

9) “How do I know I can trust anything you tell me now?”

Trust is the indispensable ingredient in every relationship, and when it goes missing then love tends to leave soon after. 

There’s every reason to now doubt the bond of trust you thought you had. 

Him being unfaithful calls into question everything he’s ever said to you as well as what he’s saying to you now. 

So why should you trust him at all?

Love is just so difficult, and many times we end up completely dependent on someone else and allow them to treat us in ways we should never accept. 

It’s possible to turn this around and empower ourselves, however, in ways that might really surprise you. 

I found out a lot about this from the shaman Rudá Iandê. 

Like Rudá explains in this mind-blowing free video, many of us are trapped in a vicious cycle in our love lives. 

We end up trusting people far too much and not trusting ourselves. 

As he delves into, there’s a different way to approach love and intimacy that works much better!

Click here to watch the free video.

10) “What would you do if you found out I cheated on you?”

This question puts the shoe on the other foot. Ask him how he would feel if it was you who’d run around on him.

This helps him see it from your perspective and hopefully empathize with you a bit. 

Unfortunately, some guys have a real double standard where they expect a forgiving and understanding girlfriend, but they wouldn’t necessarily return the favor in your shoes. 

Helping him think of it this way gives him more compassion for what you’re going through. 

It also makes him aware that you don’t have to forgive him. 

You have options, and you do have a voice and a choice. 

And he may well be getting kicked to the curb any minute now if he doesn’t come clean with you. 

11) “Why should I give you another chance?”

Here’s where you offer him the chance to make his case. 

There is no real “right” answer, of course, but a mature guy who respects you is going to admit that you really have no obligation to give him another chance. 

He’s going to emphasize that he loves you and that he won’t ever even think about cheating you again.

He’s going to treat this like he wants you badly and would hate to lose your love. 

If he pleads and tries too hard to act like a lawyer arguing his case it’s more questionable. 

Even worse is what some guys do by deciding to switch to the prosecution and accusing you of cheating, flirting, or otherwise having deserved what happened. 

This kind of gaslighting might include saying that what you did (or didn’t do) pushed him to cheat or made him unhappy. 

Any such attempts to shift blame onto you are strictly not kosher, so don’t tolerate it. 

12) “How do I know you won’t do this again in the future?” 

When a guy cheats once, what’s to assure you he won’t do it again?

This relates back to the issue of whether you can actually take his word.

So, can you trust him? Ask yourself the following questions: 

  • Does he have a history of telling you lies?
  • Does he seem to be truly sorry or just wanting the issue to go away?
  • Does he have poor impulse control in general or is this an exception?
  • Does he over-promise and under-deliver or is that not a fault he has?
  • Do his friends and family trust him generally or is he seen as a shifty dude?

These are all important metrics to get a better idea of whether he’s the type of boyfriend who’s going to be a repeat offender or not. 

13) “Where did we go wrong?”

Asking him where you went wrong as a couple is a smart thing to ask for several reasons. 

For one thing, you really do want to know what kind of issues led to him cheating

But for another thing, you want to see how much he puts the blame on you or accepts that cheating was his decision. 

Cheating is always a choice, even when it’s spontaneous. 

Unless he was literally raped, then your boyfriend had a choice. 

He didn’t fall in between her legs by mistake and even heavy drinking or drug use was still also his choice.

He could have stopped, refrained, or went home. 

He could have called or texted you. 

14) “What future do you envision for us?”

This question gets at what he feels is coming in the future or what he sees with you down the road. 

If he’s very vague then how can you really know about staying invested in this relationship?

The cheating is a watershed moment and a stress test; it’s his lowest moment. 

If he can’t decide for sure what he wants now, then he never will. This is the make-or-break moment when he needs to lay down his cards and make his move.

You’re asking him to tell you what he really wants with you. 

Just remember that you’re under no obligation to accept. But you deserve to know. 

15) “Do you still love me?”

This question may seem overly simplistic, but it’s good to ask a cheating boyfriend. 

If he splutters too much on the answer or there are too many “uhhs” then things are not looking good. 

He should be clear on whether or not he loves you. 

If he doesn’t, then he owes it to you to be willing to admit that and let the relationship come to an end. 

If he’s not sure if he loves you or won’t answer, you then need to think long and hard about whether your love for this guy justifies the heartbreak and walking over coals that’s going to happen if you keep pursuing him or try to stay together. 

16) “Did you use a condom?”

This question may not be overly profound, but it’s definitely important to ask. 

If you’ve been sleeping with your husband without protection, you want to know that you’re safe. 

He absolutely owes you an honest answer here. 

If he didn’t use a condom even once or twice with this woman, or women, you might be in danger and should definitely go get tested. 

You should be furious if he has put your health in danger. 

Imagine how he would be in your position, and think of all the STDs and dangers out there which you might have been exposed to in this case. 

Two questions not to ask

These two questions are ones that are better to avoid. They add nothing to the discussion and can easily lead in counterproductive directions. 

1) “What does she have that I don’t?”

A confident, high value woman is never going to ask a question like this. And his answer won’t mean anything, anyway. 

Never doubt your own value and worth and don’t try to compete with this other woman or women. 

Whatever they may or may not have that you don’t still don’t provide any justification or elaboration on your boyfriend cheating on you. 

If you’re not good enough for him then he should have broken up with you, not cheated. 

Don’t bother trying to rank yourself, the fault and the blame is his. 

2) “Is she better than sex at me?”

There’s no reason to ask this, and it is something he’ll likely lie about anyway. 

If he enjoys sex more with her then he will probably deny that in order to placate you. 

If he doesn’t find her that great in bed he may shrug or play it up a bit in order to try to make you feel insufficient or somehow to blame. 

It’s a question that’s just best avoided overall. 

Sex is important, but asking a cheating partner how someone else is in bed generally results in no accurate answer or insights worth having. 

How common is cheating?

Cheating is very common, unfortunately, including in married relationships. 

Around 40% of unmarried relationships have at least one case of infidelity and 25% of marriages. 

A whopping 74% of men and 68% of women admitted they would cheat if they knew for sure that they’d never be caught doing so. 

There is no reason to give up on relationships, but understanding the prevalence of cheating and the growing occurrence thanks to apps is an important reality check. 

It’s also true that men tend to cheat more than women in marriages, as the Institute for Family Studies notes. 

Cheating happens a lot and it destroys relationships and lives. Having a realistic picture of cheating can help ensure you aren’t completely blindsided if you end up also having an unfaithful partner. 

How do motivations for cheating differ between men and women? 

The motivation between men and women varies significantly. Clearly every individual has their own motivations and context for cheating. 

However, this recent extensive poll shows that in Europe and the US, women cheat primarily because they aren’t having enough attention paid to them or feel they aren’t. Their lowest motivation is about sexual desire. 

American and European men, by contrast, were motivated mainly by sexual desire, and their least biggest reason for cheating related to feeling unloved or dismissed in the relationship. 

What this suggests is that men often are motivated purely by sex. However this in no way lowers the seriousness of cheating and calls into question a man’s commitment if he refuses to control his sexual desire in order to remain faithful. 

What are some common signs of cheating? 

Some cheaters are more discreet than others, but there are general signs you should be on the look out for if you are worried your boyfriend might be cheating on you

These include:

  • Unexplained absences or often staying late at work 
  • Canceling plans on you at the last minute
  • Showing up sweaty or looking freshly showered at odd times of the day
  • Hiding his phone from you and being secretive on social media
  • Talking a lot about a female friend or coworker
  • Displaying a lack of interest in sex and intimacy with you
  • Talking about opening the relationship or his dislike of monogamy

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