Does He Need to Know?

Apparently, she is conflicted here and cannot decide on what the right course of action is.

This past April, I broke up with my boyfriend of five years. I had been living with him for more than two years, but I broke it off and moved out for a number of reasons. One reason was that I needed to know what life was like on my own. I'd had a boyfriend since I was 15, and at age 26 I needed to be comfortable with myself and figure out if he was really what I wanted. I had doubts. So I moved out, and we broke up.

While we were broken up, I had an affair with his best friend. We'd become close over the last year through email, spending time together and so on. He wasn't happy with his life and neither was I. We supported each other. He was, and still is, a great friend, but now my boyfriend and I are back together.

He knows that I dated a few men while we were apart, but he doesn't know that I slept with his best friend and I am not sure that I should tell him. That's my problem. We're living together again - and we're talking about getting married in the next six months. I'm ready. I know that I am, I've never been more in love or confident of anything in my life. But my boyfriend says that when the time comes, we have to come clean and get married without any secrets.

I think this secret should stay with me till the grave. Any thoughts?

That secret will stay a secret only if his best friend never blabs about it, or your boyfriend does not find things from your affair with his best friend which makes him inquisitive. So the first thing here is to know what his best friend thinks of the fact that you now went back to your boyfriend and that you are apparently considering marriage. Does he approve of it? Is he spiteful? Does he want you back? You need to know his position on your new-found relationship with your boyfriend before you make a final decision.

However, it is better to believe that even if the guy is hurt, he may say that he has no problem with the arrangement and wish you well with your boyfriend. But, if he feels like ruining your relationship, or if your boyfriend offends him, or if he wants to blackmail you, he may threaten to leak your secrets or actually do it-- and that will plant a serious suspicion and doubt in your boyfriend even if you do a great job of denying it. So, in the end, you stand to lose no matter how long you keep this secret. Therefore I think you should come clean. Things like this wind up coming out to the open anyhow.

Here's a way to look at it. At the time it happened, you were not with your boyfriend; you guys were broken up. So while he might not have liked you to date or sleep with his friend, you are not technically guilty of infidelity by doing so. Therefore there is no reason for you to feel guilty. You say he knows that you dated other men while you were broken up--and so his best friend is unfortunately part of the statistic. If the man really loved you and wanted to build a life with you in it, then he will doubly appreciate your honesty in coming clean, and since it did not happen when you guys were technically together, he would understand that as an adult, you have every right to the choices you make regarding your relationship. Who knows--chances are that if he is equally honest with you, you may also discover that he knocked boots with some other woman while you two were broken up. All water under the bridge now, I say.

Start your fresh new relationship with honesty and transparency, and build on the trust and commitment that you two now seem to have found. This is because secrets between partners have a way of coming out eventually to ruin the good thing they labored to create and nurture.