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?

Ready for Lasting Love?
Ready for Lasting Love?

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.