Dear Dr. Date,
The last time I had a girlfriend was two years ago. She was a girl I really liked, and still do. The problem was that we never really had sex. This was not the problem I had. She was a virgin and I was not. So, it was expected of me at the time to be assertive and go through with it. She was uncomfortable every time we would be together so I did not push it.
To make a long story short, we never did have sex. This was right before my freshmen year in college. I started talking to and becoming more and more interested in someone else. So, I cheated on her. I know I was an *&$%$##%##@ for doing that. I have felt like an ass ever since. I never cheated before and I do not plan to do it again.
So, after a little background, here is my question. Do you think that I should tell her that I cheated on her? Oh yeah, she still does not know it happened.
The girl I cheated with knew that I had a girlfriend before college. She thought that I broke up with her. Also, do you think that there is anything that I could say to the other girl to make her understand my position? Because I think about it all of the time.

–Ex-Cheater

No matter which way you spin this story, you come out looking bad. For that reason, I’d stop trying to save your image and be honest. Since you’ve created several lies, you’ll never be able to get out of this without some future trouble. The woman with whom you cheated is bound to pop up at an inopportune time, questions will be raised, and your ugliness will be tortuously exposed.
You’ve landed yourself in this position and you should be expected to deal with the brunt of the guilt and bad feelings. With this in mind, I don’t think the first thing you should do is tell her what you did. The only goal of confessing your sin isn’t to help her, it is to make you feel better. That’s not very altruistic, is it? Your issue with no or bad sex is still smoldering and hot and I sense you’d like to tell her what you did as a not-so-subtle jab that this is what she deserves for being so difficult in bed. Even if that’s going too far, you still have to try pretty hard to explain how telling her is going to help her and not you.
We all make mistakes, especially when we’re just learning about the value of love and a solid relationship. You were a jerk. Don’t do it again.