I Cheated And I Regret It. How Long Do I Have to Pay the Price?


I am a 29 year old man who has been dating my current 31 year old girlfriend for close to a year. I met her last October at a mutual friend’s wedding and asked for her number. We began going out, and in January, we agreed to be in a committed relationship. We share many hobbies and interests, have stimulating conversations and love spending time with each other. She is beautiful (she was a former model), and is practicing as a lawyer now. Income wise, she earns more than me, but that has never been an issue and she is always happy to chip in whenever we go out. I knew I was in love with her, but I didn’t know just how much she meant to me until I nearly lost her recently. Please allow me to explain.

Prior to meeting my current girlfriend, I was notoriously known as being a player, with weekends filled with clubbing and picking up random girls. I hadn’t had a serious girlfriend for over 3 years. After committing to my girlfriend, I began missing my single lifestyle. Although my girlfriend always told me to have fun at my boys’ nights, she always wanted to know when I was home. She always wanted to know who I was with and where I was. I suppose I resented having to “check in” with her.

In March, I was having a boozy night out with some guy friends when I bumped into my friend, who I will call Katy. I always knew Katy liked me, and I was flattered at the attention she was giving me. My friend Gary, who doesn’t have much respect for monogamy, egged me on. Drunk and encouraged by Gary, I ended up sleeping with Katy at her place that night. After the event, I immediately regretted it, and messaged Gary saying that I felt like a complete jerk for cheating. I stopped contacting Katy afterwards and cut her out of my life, and resolved to be a good boyfriend from then on.

I had almost completely forgotten about this event until one day, I was napping at my girlfriend’s house and she woke me by slapping me across the face. It turns out that she had gone through my phone and discovered the messages between me and Gary where I was confessing to Gary what had happened with Katy. My girlfriend told me she suspected I had never really given up my playboy ways which is why she went through my phone to find proof. She broke up with me and kicked me out of the house.

The following week, I sent her flowers and called every day begging for forgiveness. I told her I would do absolutely anything to regain her trust and give me a second chance. She finally decided to forgive me conditional upon the following: (i) No more boys’ nights; (ii) To install a GPS tracker on my phone; and (iii) To remove Gary from my life. I agreed to all conditions; the last one was the most difficult for me to do as I had known Gary since high school, but my girlfriend believed he was a bad influence to our relationship, so I agreed and told Gary I could not to see him anymore.

It’s been a month since she decided to give me a second chance. I am grateful to have her back in my life, as I now know that I cannot live without her. However, I can’t help but feel stifled as I have no freedom or control over my life anymore. She doesn’t allow me to see female friends she doesn’t trust, even in the company of others. She watches my every move on the GPS tracker, and flips out if I forget to “check in” or report who I am with. I know I deserve this, but I miss seeing my friends and miss my freedom too. Would I be unreasonable if I asked her to loosen the leash around my neck a little? Or is her behavior now completely rational?


Let’s start at the end and work backwards, shall we?

Trust is the underpinning of any relationship.

You have a girlfriend who doesn’t trust you.

Therefore, your relationship is doomed and you should probably get out and start over.

Trust is the underpinning of any relationship.

Now that we’ve ripped the band-aid off, let me explain why I feel that way, so you can draw your own conclusions.

As I’ve said many times before, it’s either “all trust or no trust”.

You can’t partially trust your partner. If she’s talking to her ex-boyfriend on Facebook, you have to assume it’s platonic. If you’re going to a bachelor party with your buddies, she has to assume you’ll be faithful. If either of you doubts your partner’s ability to stay faithful, all trust is eroded.

The thing is, James, you didn’t have any trust to begin with.

Your girlfriend was already mistrustful of men before she met you. You overlooked that and then resented that she made you “check in”.

Factor in that you aren’t a trustworthy person. Your girlfriend knew you were a player, that you hung out with players, and that you glorified the player lifestyle, and she overlooked it. She evidently figured that keeping you on a short leash would tame you.

In fact, as you pointed out, it had the opposite effect. The more she clamped down on you, the more you wanted your freedom.

So you cheated. And regretted it. And hoped she’d never find out. But she did, and now she’s got your balls in a jar next to her nightstand.

And, not surprisingly, you’re not really enjoying the consequences of not being trusted. This is what it’s like to be in jail, dude. You stole a car for fun, the cops caught you, and now you’ve got a record. Isn’t it bullshit that they’re locking you up? Isn’t ridiculous that you have a record and that it will follow you around when you apply for jobs? Isn’t it unfair that one mistake should haunt you for the rest of your life?

Not really.

Your girlfriend’s behavior is completely rational given your behavior. What she doesn’t realize is that it’s completely ineffective.

As I wrote in “Why He Disappeared,” men are about feelings, not about looks. In other words, we may fall for someone because she’s hot, but ultimately, we stay because of how we feel when we’re around her.

I can’t speak for James here, but I’d have a really hard time feeling good about a girlfriend who couldn’t forgive my mistake and continued to treat me like a criminal. To forbid you from hanging out with your friends, to be GPS tracked and to force you to cut off a friend is — depending on your perspective – a steep or perfectly reasonable response to your infidelity.

If she can’t trust you — or won’t trust you even though you’ve vowed to be faithful — then you both owe it to yourselves to make a clean break.

No one is going to defend your infidelity.

But I will take a stand and say that your girlfriend’s behavior is indefensible as well. If she wants to have a happy boyfriend, she has to make you feel like a trustworthy human being and you have to continue to earn that label.

If she can’t trust you — or won’t trust you even though you’ve vowed to be faithful — then you both owe it to yourselves to make a clean break.

You will have learned a valuable lesson as to why it’s important to be faithful — otherwise you lose the girl and get thrown in jail.

And she will hopefully learn that the only man she should date is a man she can COMPLETELY trust. Because while you may be willing to put up with this phone-checking, friend-banning, GPS bullshit because you’re a cheater, an HONEST man will have ZERO tolerance for being treated like a criminal.

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  1. 41

    I’m a man and sorry Gary but that’s a real POS thing to do. You clearly have different ideas of what a relationship should be and you and your girlfriend are better off exes. She has no trust left for you and you’re obviously not happy either. Better to go get counselling separately as single people.

    1. 41.1

      *James, my bad. Had a brain fart for a moment there.

  2. 42

    As I read this article, I saw my own story which just hapened yesterday. My soon-to-be ex girlfriend (which I’ve been with for 2years) was very much like the girlfriend in the story. Although I never went to the club I lived that life before. And I did go to the club yesterday with my very best friend whom did not stop me because he is like Gary, he doesnt care about monogamy. After a couple shots of tequila and others, I went dancing with this girl because it seemed she admired me somehow, and thats all it took to put me on the hook juste like a fish. I love my girlfriend/ex, she is the women of my life. It’s something you feel inside. I’m 18 years old, she saved me from the old me(I was ruining my life with drugs). Since then I am an A+ student, she cared about me the way I cared about her, and I still cheated. I don’t know what happened, I was not myself, because I would never do something like that. Kissing another girl was not pleasurable, I did not like anything, I felt manipulated by “Gary”. I feel betrayed by myself, and I can imagine how my girlfriend/ex feels, but I don’t want to lose her. I flushed 2years of our lives over the feeling of being a big boy or whatever.

  3. 43

    I feel like checking in with someone is part of being in a relationship. You are partners not just friends. If I date someone I want us to be best friends and lovers, tell each other everything without asking or begging. I don’t think that it’s a sign of having trust issues (although it depends). I believe when you meet someone and you get to know them you decide whether they are trustworthy or not before you even get in to a relationship. Without trust I wouldn’t go in to the relationship in the first place. If James didn’t tell me he was a player, having a problem with checking in with your girlfriend (someone you are committed to) already tells me you are not used to being in a committed long-term relationship, because this behaviour is normal. Hell, even my parents do this and they are the most trusting couple I’ve ever seen.

    Unfortunately I have been cheated on before, that made me do a lot of research on professional opinions on how to trust a cheater and do you know what the common advice was? I needed to have him prove to me that he could be trusted, the way to do this is to have rules in place that would make me comfortable, that would build my trust. You can’t break trust and expect it to materialise again over night. I ended up not taking him back because I knew no matter how many hoops he jumped through I would never trust him again. It’s because of this that I struggle to understand why so many people take someone back after cheating, to me cheating leaves an everlasting mark on your relationship and on your psyche, it cannot be covered up by regaining trust. Furthermore, the thoughts of what happened and what could happen will torture you.

    So yes, I do understand where she’s coming from with the ultimatums to build trust (even though I don’t understand taking someone back after cheating) but my eyes did widen considerably when I read the GPS tracker bit. I don’t think that stalking some ones every move is healthy. Something like that could lead to obsessive neurotic behaviour. I’m not sure about the friend bit, I understand not wanting your partner to be around someone who is a bad influence especially if that person is the same person who will egg you on and sit idly by while you do something destructive. I feel like she shouldn’t even have to tell you to drop the friend, you should want to drop the friend. I don’t want a friend like that, I don’t want someone in my life who is going to encourage destructive behaviour, I’m not talking about TP’ing someone’s house like you’re back in high school or typical men just being silly type of stuff. Of course that’s just me, I like quality in my friends.

    I also think you should have told her yourself. Another thing, I don’t think snooping is okay unless it is permitted snooping but I also think if someone gets bent out of shape over snooping and puts passwords on their phone (I know he didn’t use passwords just saying) That seems like untrustworthy behaviour, what are you hiding that you don’t want your SO to see? I get the whole invasion of privacy but after you’ve invaded each others privates I’d think that there shouldn’t be anything to hide. What is there that is “innocent” that you don’t want your SO whom you love and want to spend your life with (hopefully) to see? Do you work for the government? Are you a spy? Cause that seems like the only legitimate reason.

    The reason I feel like this about snooping is because this is how I found out that my ex cheated on me, granted I had permission to snoop. And yes I gave him countless occasions to come clean. Unfortunately with permitted snooping he usually deleted all the evidence but men get lazy and careless. They become used to routine so one time he successfully deleted his inbox messages but forgot to clean up his out box. Anyhow, even though snooping is bad it has saved a lot of people from oblivously marrying a cheater or continuing to think “well this is weird but I believe you when you say nothing’s going on”.

  4. 44
    Betrayed Husband!

    The fact is, she’s had so many guys, always inflicting so much pain, when it came to her,   she now (for some reason), never or doesn’t seem to know the difference anymore (which is sad), Mr, “So-Called, (Fake Ass Guy), loves to pretend, let’s her think, that he is still her “fake boyfriend,” which… let’s   him think he can still do whatever, the fuck he wants… When it comes to her….. (think), realize for yourself that all this time (while he tries, pretends to live a normal life), how this is affecting you and you don’t see the fact on   how he’s fooling everyone (well, he thinks he is), this includes us, toying with you the most and you don’t see this for yourself? grrrr, thing…. is… so… selfish…. and stupid!….   blah, blah, blah.


    Now me saying, “Why do you keep doing this to yourself?   Just stop already!   I hate seeing you go through this (this heartbreak), alone 😢!   Please, it’s breaking my heart as well and praying that you would stop trying to fool everyone, even yourself…. just stop already!   Your better then this.   Can’t you see? I know, because I always believed in you… and I’m tired, just tired of hearing (reading), all of this bullshit!   Open your eyes!   Just wish you would for once, realize all the pain that your putting yourself through (it’s selfish of you) and others, me included……   really?” People, sometimes we (friends who care), we just can’t help it, but want to always be there, for our love ones, even the ones we once had… that were very special to us, (even an individual) from our past… a happy life that was once shared…. together” (this includes me)…


    Now back to you!   Your better then this!   He’s nothing but a “piece of shit”, and hate the fact (because he took advantage of our friendship/love), this ass-whole, and I place a lot of fault on him, he has a lot if nerve (because of this advantage, he once took, but seems to still have), I’m paying the price too everyone (I’m sad)…. all these results because of this, his actions, plus your actions, and you know this…   especially from the results, yours (plus his), and all of it from this ripple you once caused with him?   Freak’in dumb…. not worth this bullshit, all this pain… this pain… period! It’s hard for me seeing you like this.   Sometimes, I wish, I could be there for you!   Everyone, try to understand why I say this (this plead of mine), it’s coming straight from my heart…..(because i’ve learn to accept my punishment, haven’t I?), all these past years and this is one person that would never…. have left her side, period!” God (praying to you once again), “haven’t I been punished enough?   please, just let her go… from this terrible person that pretends…. he thinks that he could, and would always… play mind games, which includes her heart.   God, please just stop punishing me (because you keep letting me view all of it, still), but please give her back a regular, a normal life once again… again like before! (I don’t need to be in it) Let her be happy, give her back a normal life, especially a life, with someone that would love her, listen to her, care for her and will always be by her side during these hard, rough, scenarios in life,   general speaking (this is the whole point, of my prayer), now whether…   this includes me or not, just give her back a normal life once again!   Realize God,   I don’t have to be in this new life of hers!…. God, please just do this last favor for me, for once…. please! Thank you, Amen!”

  5. 45

    When someone is cheating on you, it’s the worst betrayal.

    I’m trying my best to understand where the girlfriend is coming from. She has every RIGHT to feel angry hurt from her boyfriend’s actions. Although he’s do whatever he could to gain her trust back, he shouldn’t have to pay the price for the rest of his life. Asking him to end a friendship with someone from high school, and have a GPS tracking on his cell phone is beyond extreme.


  6. 46

    Wow! She’s beautiful, intelligent,   pays on dates and he still cheated? Some people are never satisfied…

    If I were her I would have broken up with him for good. Why waste your energy taming a player when you could be with someone else?   This “relationship” sounds like misery for both sides.


  7. 47

    This is so simple. They are a terrible match. James is a whiner, and deserves a women who cheats.

  8. 48

    If I may ..

    The reason why she is being ‘controlling’ as the people here would describe her behavior.. Is because she was obviously nuts about him.

    Feeling so passionate about the idea of losing somebody isnt a bad thing.

    Passion is what often makes things in this world great. With love it is no different.   She obviously had found somebody who she was willing to invest in and needed to know what was up. She’s not stupid.   She picked up a bad vibe so checked out his phone. I would read thIs action as she didn’t want to accuse him because she values him that much . This is alsO why she is hanging on.

    Listen, if you find somebody even once in a lifetime who is that crazy for you and you are worth your salt , you will know to lay down your little black book and never look back… You’ll live once and you’ll only get older and older … People die, they age and as they do the chances for love become less and less.   There  is NOTHING like living a good long life with somebody, giving and sacrificing and having the kind of love that you feel from a person who knows you have done the same for them.   It’s a gift.

    No quickie or thrill or chase or new face can compare to a long run of honest abiding love, but you can’t and won’t ever know the feeling if you look back and haven’t done it.

    I have. It is beautiful. So very much so.

  9. 49

    Bruhh you done fucked up. She caught you red handed and she still forgave your sorry ass. Now that’s something worth keeping. Just face the consequences if you want it to last and if not then like the author had said, “Make a clean break”

  10. 50
    RENEe bebawi

    You’re grown man you did it cuz you wanted to. why did you want to though?     you miss the I miss the single life but did you ever ask yourself why if you have the perfect girl? And your girlfriend definitely has control problems she clearly doesn’t realize that what you do voluntarily verses forcefully is a lot more rewarding and fulfilling.   the path you’re on clearly shows that your relationship will end because both of you will feel dissatisfied.   if you made a mistake if you made a mistake and you’re genuinely sorry then she shouldn’t even have to follow you around it should be from you voluntarily to I want to be open and include her in your life.   just want to be just want to be as open as a clear blue sky.   and and she’s never asked you any questions she needs to ask you because it’s also her decision to be with you and to make a decision a good one she needs answers,   clearly.   it might take time to decide what the final outcome will be based on what you learn about each other and yourselves ultimately through the process.   and if and if you actually allow yourself to go through it whole heartedly it may hurt as growing pains do but it’ll help you define who you are and your intrest indefinitely and it’ll mold you into a better version of you. With all that said it takes two and unless she let’s go and lets nature take its course she never really know who loves her. But that doesn’t mean you shouldn’t try to show her that you are the man she can trust respect and love,   if in fact that’s how you feel. if you’re unsure then the   right thing to do is let her know that you’re not sure exactly how you feel. that you care about her and you think your feelings for her are genuine and that you want to give to try as if it’s your first time together and you want and need to get to know her and yourself and who you can be together to   really know if will grow, set up time stamps every few months   and check in with each other. communication honesty and loyalty are key ingredients to self growth,   so essentially all those things are really not for her; they’re for you to humbly hold your head with pride and without saying a word demand respect. when you can do that you’ll both find love maybe in each other or with someone else but regardless you helped someone else grow by just witnessing that people like that do exist and you,   You came out a better person than you did going in.


  11. 51

    So are you saying if he tolerates the rules she has put on him that he is still a cheater?

  12. 52
    Lone Rose

    From what i can pick up about the writer that cheated, it sounds like he is still not mature, and wants to live a party type ‘highschool’ lifestyle at the age of 29. However, he also wants the perks of having a stable, nurturing, forgiving type girlfriend at home waiting for him. Well, he cant have both.

    He can either continue to live his bachelor party lifestyle to the fullest, or surrender to a relationship that sounds very controlling. In my opinion, if she doesnt trust him, then why is she still with him and keeping him on a leash as if he is some sort of dog?

    I actually dont think its healthy at all for the two of them to stay together, and the longer they stay together, the more toxic their relationship will become. He should live his party lifestyle, and then he can be free to date as many women that he likes, until one day he might change and become faithful and stable, but until then he should not be with a girlfriend who wants someone stable and loyal, and she cannot FORCE him to be that way, i mean a G.P.S tracker? that sounds really toxic and not a healthy relationship to stay in at all!

  13. 53
    Alice Dragomir

    I kinda felt in the same place with James. I don’t think it is considerd cheating when you kinda help your BFF with some useful bedroom tips. ( I am a lezbians . btw) she did not know how to do things so I showed her. After that day I began to feel guilt. Lots of it. I love my girlfriend to death and feel horrible about what I did. Not only a couple day later did I realize.. That it was really cheating. You know about eating people out and stuff… Well I kinda did to show her how to do those things for her girlfriend…..

  14. 54

    I sincerely hope the OP broke it off with his girlfriend. You’re just not healthy for each other. You don’t love her enough to maintain a committed, monogamous relationship and she doesn’t trust you. It’s not good for either of you.

  15. 55

    James – you are a cheater, and will likely cheat again.
    Your girlfriend should have had a zero tolerance policy and asked you to go
    and not call. It might have helped you to learn that cheating is the ultimate
    betrayal and everything else in a relationship is piggy-backed on that fact.
    Some people subscribe to the notion that cheating can be healed and it can
    with another significant other – but not your gf. She will never trust you completely
    ever again. (Hint for the next gf – stay sober – being drunk isn’t a good excuse)

  16. 56

    I really can’t get past the fact that this girlfriend slapped him. Nothing about James cheating is defensible, but violence is never acceptable in a relationship. If I were James, I would hightail it out of this relationship and resolve to (1) find a new partner who knows better than to hit someone in anger and (2) learn to be faithful next time. This relationship is broken, and it’s not only James’s fault.

  17. 57

    your girlfriend is a former model and lawyer and who are you? seriously,a player? No sir, you’re a dumb ass if your story has truth to it.. What kind of dimwit let down a woman who’s beautiful, independent, in one word is high caliber? I wonder why she still stays with you? what does she in you? a player and cheat?

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