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When I Tell Her I Have Cheated

Eventually, the question always comes up. Have I ever cheated? And I always give the same answer: Yes.

Then, from there, the follow-up questions breaks off into one of two directions. Either she wants to know more about the times I cheated or she wants to know why I cheated. To both questions, I try my best to answer without over-explaining, but rarely do I ever avoid falling into such a trap. Because I’m a natural talker, I always end up giving the who, what, where, when and whys of what happened. And usually that is when suspicion begins to creep into the mind of the woman who asked me the question.

I suppose there’s a reason to be suspicious of any man who so willingly cops to their past mistakes; who says, almost brazenly, “Yes, I cheated.” I don’t blame any woman whose expectations or enchantment with me comes back down a little bit closer to Earth when I tell her I’ve been unfaithful to women from my past. Shoot, I almost expect this to be the case.

But when I tell her I have cheated, when I admit I haven’t always been the best man or even a good one to women from my past, I expect an open mind to the possibility that I won’t do it again. Maybe the benefit of the doubt is a little bit too much to ask, but how about the benefit of some understanding, not towards past indiscretions, but rather, the understanding that the past is the past.

I understand an admittance of guilt does not make me any less guilty, but I don’t admit to cheating so that I can be viewed more innocently. I admit to my past mistakes because to do anything less would be just another set up for more skepticism. I cheated, and when she asks me if I ever cheated, I give her the answer she expects to hear, because if I didn’t, she wouldn’t believe me anyway. The other reason I don’t hesitate to answer with an unequivocal “Yes” is because I’m not ashamed of it. Talk to a man who has served time for a crime they committed, and you’ll understand what I mean. Once you’ve been caught doing something wrong, there’s only consequences for the truth moving forward.

Now don’t get me wrong. I’m extremely sorry for anytime I ever cheated, but how I resolved that always will remain a thing between me and the girl I cheated on, not the girl I’m talking to about the girl I cheated on. I’m ashamed to no one else for what i did to someone else, and I think it’s that attitude I carry with me that seems to rub some women the wrong way. They mistake the comfort I take to admitting my mistakes to mean I will do it again, as though my past speaks for me, when really it only speaks for itself.

When I tell her I have cheated, and I don’t bat an eye when I say that I have, this does not mean I am completely comfortable with ever doing it again. It means, I’ve been there, done that, and no, none of it was pretty at all, but it was all so…then.

To this day, I feel the question of whether or not I cheated is a setup question, one of those reasons women go fishing for when they’re looking to cut me off either at that particular moment or later on down the line. And though I do completely understand why a woman would want to hesitate to get involved with a man like me because of the other times I cheated, I hope she understands this: When it comes to trouble and guys like me, there’s no running away because there’s no place that far. The only thing there is, the only thing there ever will be, is the truth and how we deal with it moving forward.

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  • Hugurl

    Men will never learn. 99.9% of women would never share this information even if it’s the truth. I think it’s more for the Former cheaters comfort and peace of mind. If you’ve cheated (ESP if it’s been more than once) you probably have a fear of getting caught up and thus needing to admit to prior indiscretions seems like a no brainer( don’t want her finding oh lager). My thing is if you don’t intend on cheating on this girl why tell her? Yes it’s nice to tell the truth but as adults we have to learn when the truth will help, when it will hurt and when it both hurt and help–I think you should only tell if it will help in se way–telling a girl you’ve cheated before may not hurt, but it certainly won’t help.

  • Ava

    I thought this post was going to be about you telling your girlfriend you cheated on her. But anyways, it got me to thinking about why that question gets asked. I have asked it but the answer I received hasn’t ever made me reconsider dating whoever I am dating. At any rate, good post!

  • B

    To be able to speak the truth and be honest is far more respectable and courageous than to be deceitful and shady, any woman with the right head on her shoulders will tell you this. Thank you Jozen for this blog. Many times people think that lying is a way of protecting a love one’s feelings, when in all reality, it will do more harm in the long run. Any relationship were fighting for is worth such courageous efforts of honesty.

  • mimi

    Oh what! Who cares if you cheated on your ex!? Any girl that does is super petty if she cares about the details of you cheating on your ex beyond pure entertainment. I thought this post was going to be about you telling your girlfriend that you cheated on HER. The game changes if that is the case.

  • Rashad

    I read Hugirls last long sentence and I got totally confused. It makes no sense. But in terms of this entry, I admit to cheating if asked. Its not a big deal. Situations have to be taken on a case-by-case basis and if I get written off by a prospective woman because she’s upset with my conduct towards a past woman, then oh well.

  • tihawkins

    i’ve cheated. it’s a part of MY story. i stole candy as a child, as well. … it’s called growth. anyone harping on things you’ve done in the past, will eventually end up there.

  • HoneyMoney

    I’ve never cheated in a relationship so I have no understanding of doing that type of thing. Really I don’t. That makes it difficult for me to not judge someone who has cheated. Because for me, I don’t really see a good reason for it, which is why I’ve never done it. And in an ideal world, people who make these type of mistakes can grow from them and not do them again, but many cannot and have cheated more than once -which is disappointing and for me, not acceptable. There is nothing I hate more than a person who just can’t speak up and say, “I don’t want to be in this relationship anymore” and chooses to cheat instead. Its extremely selfish and also patronizing. Sorry, I am probably the only person who has a problem with this! And I know some of my ex’s have cheated before and have still continued to be amazing boyfriends to me, however…it still doesn’t sit well in me. I am always weary of people who make bad decisions, as their bad decisions no matter what kind, can always effect me too. To cheating is just illogical, but yeah, that’s just me.

  • **inquiring mind**

    @HoneyMoney Wow… you must be a saint.

  • Theryl

    The post was very honest. But the risk with the honesty is that it may come off as boastful or prideful. Of course the honesty is appreciates, but that same honesty creates the “well he’s done it before” situation. Damned if u do tell, damned if you don’t.

  • **inquiring mind**

    Good post Jozen. A friend and I were talking about this except his ex asked if he ever cheated on her when they were together… While I know you, Jozen, don’t speak to your ex’s- smh… I am curious as to why men don’t admit when they’ve cheated on you once the relationship is over. I remember asking my ex if he ever cheated on me, just out of curiosity (I honestly had no interest in him at that point either way) and he said no… I however know better. Why can’t y’all just keep it 100?

  • Alana

    This was an incredible candid post, I enjoy that.Jozen when we ask you if you have cheated its not really a set up at all.We just wanna know if your as honest and open as u seem to be.

  • Conscience

    @ Inquiring Mind

    Lmao you’re funny. Why be 100? So you all can go back and blast us on the street. So you all can see us walking in the park with the replacement and yell, “watch out girl, you got a cheater on your hands.” We all know a lot of women love to hate. Why provide the ammunition. If she’s your ex and you cheated on her, you have already lied to her, no need to stop now lmao. Now admitting to having cheated in the past to the replacement, or the new chick, is always a good start. You never know where it’s going to go and if she ends up being “the one” starting a great relation on a lie is never worth it.

  • **inquiring mind**

    @Conscience You’re so dramatic… I for one (I can only truly speak for myself, right?) just wanted to know… call it closure if you want- I felt it in my gut (dats what she said-lol, I digress). The ex deserves the truth just as much as the next chick deserves the truth… I would go as far as to say the ex deserves it even more so. And, you really have nothing to lose at this point by telling the ex. Any woman who would take what an ex says i.e. “watch out girl, you got a cheater on your hands” over learning who you are for herself wasn’t worth your time no way. Point is everybody deserves the truth Conscience.

  • E-Dub

    Am I a cynic? Any man over thirty who said he’s never cheated would seem suspect to me. Not as suspect as the thirty year old who claimed he’d never masturbated, but still. It gives me some comfort to know my guy has already been through that, and lived through the horrific aftermath and repercussions. By the time he gets to me, he’s like “that shit ain’t worth it”.

  • Conscience

    @**inquiring mind**
    You’re right everybody does deserve the truth, but some people can’t handle the truth and that’s just the truth. Not saying you can’t, you come off like a real enough chick so you probably can. It’s just a fact that some men/women just can’t handle it. This is easily an oxymoron, but I think almost everyone has cared about someone enough at some point that they lied in order to spare that persons feelings. Counter intuitive but factual none the less.

  • Sunkissed404

    @**inquiring mind**
    Apparently Conscience has no Conscience…

  • Yesi Jukebox

    “but how I resolved that always will remain a thing between me and the girl I cheated on, not the girl I’m talking to about the girl I cheated on”

    I truly believe that the subject of cheating is a relative one, it is to be dealt with by the people’s unfair to judge someone you want to be with by their actions in a past relationship. We will never know exactly what went on with that relationship and trying to understand why cheating occurred might be delving too much into something that is not our business.

  • purp

    They ask because either:
    they wanna stay stuck on the past
    they wanna have a clue as to what to expect in the relationship
    they’re immature
    and @ InquiringMind why ask after you guys broke up??? It’s not gonna change anything.
    Basically two questions that should never be asked are, how many people have you slept with and have you ever cheated. Why? Cuz it ain’t got shit to do with the other person. Just cuz he cheated before doesn’t mean he’ll cheat on you.
    People are always trying to map out habits and patterns….and what they always forget is that people change! we grow, we evolve.

  • ExAmino

    WAIT a minute. I understand that the past is the past. But it’s stated above, “as though my past speaks for me, when really it only speaks for itself”…..if someone has cheated multiple times I believe one’s actions and decisions speak loudly of your character!

  • Conscience

    Oh I do, just sometimes it’s a guilty one.

  • Sunkissed404

    I have never asked anybody I dated whether he cheated or not in his past relationship. I have never had to ask ….The topic usually presents itself when I am having a serious conversation with the person. When you first meet someone, the one question I am asked is “How long was last your last relationship” and “What Happened”? I will willingly answer the length of time I was in a relationship, but I stay away from answering “open-ended” questions like “What happened”, because just like Jozen, I am a natural talker, and will give too much, too soon.

    I have never asked another guy if he cheated tho’. I feel that might automatically put him on the fence, and make him think I am anticipating him cheating on me… Don’t do it!

  • Sunkissed404

    Lol… I set myself up for that one…. You a tripp!

  • Dewan W. Gibson

    I’m not sure if admitting to cheating in the past is the ultimate form of honesty. If a man wants to be completely honest he would say “I’ve cheated in the past. And there’s a fair chance that I’ll cheat again. Especially if an opportunity comes along where 1) The woman is interesting and 2) My chances of getting caught are low, such as a time when I’m out of town. But if I cheat on you it doesn’t I don’t love you”

    That’s honesty.

  • **inquiring mind**

    @Conscience I guess that’s the difference between the two of us… you use lying as a form of protection (either for them or yourself- but prolly yourself more than anything), I on the other hand see the truth that way (as a protector from assumptions, the imagination and- no pun- our conscience). Not to mention, you never know how someone is going to take something. How can you protect someone when you don’t even know what you’re protecting them from? Men make women out to be these fragile creatures when ultimately y’all are the fragile ones. Y’all don’t want to be honest because you’re too proud to admit you’re wrong and too selfish to accept the consequences for it.

  • MadScientist7

    i don’t understand what a woman’s reason would be for asking me if i cheated in a past relationship. it’s the past and that shouldn’t matter as long as i’m faithful to HER. that’s the equivalent of me asking how many men she has been with prior to me. both have nothing to do with our current relationship. if my current asked me that i would kindly tell her that it is none of her business. *shrug*

  • Calikid

    This is a great post man. I definitely think the question of whether or not one cheated is a set question for the women to have a reason why she can’t be you. And you’re right. If you say no, they assume you’re lying, and if you say yes, most of them make a big deal about it. I think only insecure women make a big deal of a “yes” answer to the cheating question. Some people cannot handle the truth and are not aware of the fact that your past does not always dictate your future.

  • **inquiring mind**

    @MadScientist7 I’m not even trying to be confrontational or commenting so much- contrary to popular belief I do have a life (of some sort)… but anyway, I am so sick of people (and by people I mean MEN) complaining about someone wanting to know/understand their past… Da phuck! It’s apart of who you are, why you hiding it? If I ask about your ex’s, or if you cheated, or if you’ve tossed salad… I’m just trying to know you- I’m not collecting evidence- sheesh. .. stop acting like criminals.

  • goalawal

    I think cheating is all measured good or bad based on your moral compass. I in a way feel like you need to cheat to find out whether or not you want to be with whoever ur with. cos if you get caught or NOT it could help put things in perspective as to whether or not it was worth it. Life is about growth and whether its about cheating or NOT if you ask me a question i will answer truthfully…If you want to judge me, go take the fucking Bar exam and be behind me like my past.

    CHEATING is the greatest but possibly the most fatal test of ones relationship… I will rather cheat, regret it and learn from it . Have people no idea of what Non-Americans think of cheating.. E.g Tiger Woods popularity soared in China after his debacle apparently cos your idolized based on how many woman you bed… Sucks for his wife but it apparently wasn’t bad for business or the I-phone apps that came up afterward… Dont even let me get into how cheating is perceived by some in Nigeria let alone many African countries…

    I LOVE you but i will promise to make you happy.. break your heart and work harder to mend it and make you happier.. So, have i cheated? Well, it depends on who exactly is asking.

  • Erica

    I ask the question because the way a man answers it (whether in the affirmative or not) tells a lot about him.

  • BoomShots

    Every time one of those high profile cheating stories hit the tablods it never fails for whomever I may be dating at the time to try to interpret my history or my feelings on infidelity. My approach in these situations is to be bluntly honest, don’t ask anything if you not prepared to deal with the answers.

    i have never cheated, meaning i have never had sexual relationahips with another person while involved in an exclusive relationship with a specific woman. Defined that because so many interpretations exist as to what comprises cheating.

    But I am never join in on any chorus that cheating is only second to murder and i should condem anyone whose ever done it. I find there are women who wish me to submit to some blood oath about cheating and I refuse because its too complex an issue to reduce to simple cliches. I have friends, family and acquaintances who have cheated and that alone does not make them bad people or evil in my estimation. But then whenever I was unahappy in my own past relationship I would just move on, not everyone has that option.

    Past behavior is a predictor of future behavior any odds maker would tell you to bet on that so being ignorant of your partners past fidelity is no defence. Context is important and so I would not be adverse to a woman questioning mine own past relationship behavior since i will be as observant of hers. Its popularly called baggage!!

  • MadScientist7

    @**inquiring mind** so you would be willing to answer any question about your past that a man asked? answer honestly now.

  • MadScientist7

    @**inquiring mind** on top of that i feel like some information is pertinent to our relationship and some information might be asked because she is just nosy. if i feel like it’s that latter then it’s not getting answered. plain and simple.

  • HUgurl

    Yeah, it was late night and I was on my phone. What I meant to say is that honesty isn’t always the best policy. You should really only tell somebody the truth if you think it will help the relationship in some way and I don’t see how admitting to cheating with a NEW girl is going to help. Like at all. If you lie, so what? Would she know? nope. All you’re doing is planting seeds in her head. Unless you’re a serial cheater there is no need to disclose the time you got head from some random chick while you had a girlfriend. WHAT IS THE USE?? I get that you want to be honest, but if people are so concerned with being honest, why not get STD tests with every new partner? Or ask when the last time they lied to their partner about anything? Those are also important questions to answer truthfully right?

    I just think telling people about old relationships is not a good look, any girl who asks is hoping you lie to her. Because if she really wanted to know about your integrity in a relationship she wouldn’t be asking you if you cheated, she’d be observing your actions and making a grown woman decision.

  • **inquiring mind**

    @MadScientist7 Why you being so defensive Pookie? gosh… I would answer actually… I have nothing to hide. And, nosy or not we’re women WE WANT TO KNOW (well some of us)- so what? Don’t be a baby about it.

  • MadScientist7

    @**inquiring mind** i’m not being defensive. lol i just find it funny women want to know all about a man’s past but when the shoe is on the other foot all that shouldn’t matter. *shrug* how about we hug it it out. lol

  • **inquiring mind**

    hmph… hug deez- I kid I kid. 😉

  • **inquiring mind**

    hmph… hug deez- lol- I kid I kid… 😉

  • **inquiring mind**

    oops… You know what Jozen… You gotta do something about these damn “correctionless” comment sections- this isht’s for the birds!

  • Sunkissed404

    @**inquiring mind**
    OMG- ROTFL!!

    You are Fuh-Nee… You have passive/ aggressive tendencies. lol
    Be a good sport IM…You can dooo it. lol

  • Sunkissed404

    @**inquiring mind**
    Sidenote… You shoulda been on that Nightline Panel they had in Atlanta a few weeks ago. You woulda gave Hill Harper and Steve Harvey tha bizness…lol

  • **inquiring mind**

    🙁 Why I gotta be passive/aggressive?

  • Sunkissed404

    LOL.. Oh lighten up.. You speak for at least half of the people who read the blog and never comment.. 🙂

  • **inquiring mind**

    dey prolly just know better *shrugs*… no home training- lol

  • Jonathan

    @MadScientist7 Why you being so defensive Pookie? gosh… I would answer actually… I have nothing to hide. And, nosy or not we’re women WE WANT TO KNOW (well some of us)- so what? Don’t be a baby about it.

  • Sunshine

    After a woman asks a man if he has cheated, it’s his reaction that we care about. Your “yes” without a flinch, and the fact that it’s “women” versus a “woman”, is a huge RED flag. Any woman who hears that from you, should run away quickly. You don’t realize that you owe more than the woman you cheated on an apology. Any woman you care about is owed something extra to prove your loyalty because you are clearly a “cheater” by trade, lol. If a man says he has cheated, but it was a huge mistake with a lot of consequences, and he’s really sorry for what he did, that makes him more human and desirable because he is capable of feeling guilt which is somewhat a comfort that he won’t cheat again. Because he’d feel too guilty.

  • MissMina

    I don’t understand how guys can post on here like its unreasonable for a woman to ask about his cheating past when almost EVERY guy I know will ask a woman how many partners she has had. And yet conveniently, the past is rarely the past when it comes to your “number”, especially for guys.

    As far as telling the truth, right on Jozen. Cheating is based on deception so for you to lie about it shows that you haven’t changed. And whether she finds out the truth or not, you have already introduced dishonesty into ur relationship and that will make it harder for you to be honest in the long run. I think everyone should cheat at least once in their younger days, just so you can feel the burn and not be tempted to do so in the future.

  • HeadMistress

    I have and will continue to ask this question of men that I consider having a relationship with. Not to be nosey or judge harshly but it’s a behavior that gives me an idea of your overall character.

    I don’t get this “the past is the past” reasoning – our pasts make us who we are now, so if a person’s past has been a training exercise in selfishness and deceit, then yeah I need to know.

    That’s not to say any man who has cheated will be dismissed cause then I’d have to just settle for being alone, but his “reasoning” (there is no good reason as far as I’m concerned but there are SEMI-understandable ones) behind it and whether it’s been a habitual occurrence in every relationship is just as important to know.

    Let’s not forget that we’re talking about sexual behavior and that is Life & Death Isht!

  • JustEnough


    Conscience, you can live with yourself? Lying an or telling half truth and whole lies to “the one”? Having a “guilty one”, really? I would hate to be your chick!

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  • NinjaOnOver

    Wow. I’m 7 yrs deep. Anyway, Exactly. I call Bullshit. Especially since I’ve been going through posts and he’s cheated multiple times. On women he didn’t care about and on a woman he loved (causing her to feel at fault)

    And then the Author busts out this “the past is the past” bullshit. No.

    That’s why there are things called Patterns, and Profiling and Conditioned Behavior.
    A woman has the right to ask, judge your character & hopefully run far away.
    (yes I’m a guy)