Dear Rabbi Shmuley,
I had a promiscuous period during college. I am a new woman today and would never behave this way again.

During the end of my "bad period," I began a friendship/courtship with my current boyfriend. After getting to know each other slowly, we fell in love and began dating. We waited a good long time to have sex.

I really was able to heal myself during our friendship and later dating, and reclaim my strong values about the importance of love going hand in hand with being intimate. The problem is that my boyfriend recently asked me how many people I slept with, and I couldn't bring myself to tell the truth. I told him I was deeply ashamed about being intimate with people in my past, but that I had only had actual sex (rather than "hooking up") with three, rather than eight (including him). He was able to accept the number three--which includes himself and the other two boyfriends I have had. I am sure that eight goes too far for him, since he once mentioned that if I had "slept with like ten guys," it would be a deal breaker.

I am afraid to tell him the truth. We plan on raising a Jewish family with strong values. I'm afraid I'll never find someone who places such a strong importance on family values as I do but can also accept my past. It would kill him to have to look at me and think of all these other men who have come before him. But it doesn't seem fair to have to pay so much for my mistakes from the past! I wish I could take what I've done back--with all my heart. I am also prepared to channel the guilt I am feeling into making him feel special and loved.

But it doesn't seem right to be dishonest to someone I love. I am distraught. Is it wrong for a woman to have a family with a man when there is a secret like this in her heart? What if it is something from her past that is just that--in the past?
--Ashamed and Afraid

Dear Ashamed and Afraid,
I hear the anguished tone of your email. I understand how painful it must be to feel you have to conceal an essential part of your identity from someone you love so much. Clearly the whole purpose of being in a relationship is being able to be utterly vulnerable, open, and naked (in the metaphorical sense).This means you have to remove all of your defensive armor and feel that you are accepted for who you are.

In all areas of life we are judged by what we do, how we present ourselves, the impact we make, and which accoutrements of success accompany us. It is only in a loving relationship that we are judged by a completely different criterion, namely, what we are, as opposed to what we do. It is our being which is embraced and not just our doing.

Hence, your feelings of anxiety and your fears of rejection are very understandable—you're concerned that if your sexual history were known, you would not be loved by the man whom you love, and whose affection you seek.

Here is my suggestion to you. We all make mistakes in life. We all do things that we regret. Wrestling with our humanity is the very stuff of living. In life, righteousness is defined not through perfection, but rather through struggle. It is our endeavor to try and do the right thing that makes us unique and special.

The bad things that you did in the past--agreeing to be intimate with men who may not have loved you, compromising your sense of intimacy and dignity--those things are all in the past.They are no longer who you are. When we repent of the bad things that we do, then they are erased and they are obliterated and they no longer stick to us. In Jewish teaching, when people change their ways, they are not even allowed to be reminded of their former ways because those ways apply to a different person and not to them.

What I am saying is that you should certainly not share with your boyfriend the fact that you have been with many men. It was not you who was with those men. Now that you truly regret those actions, have changed your ways and have committed to a better path, you have become a different woman.

You have changed, you are new. To bring that up would be bringing up a stranger, a foreigner. And this is especially true because your convictions have changed.

You write to me that you regret what you did, that you went through a difficult period, and now that you no longer believe in that kind of lifestyle, it is no longer a part of you. Do not tell him a thing about your sexual history, because it is someone else's history.

You must go into this new relationship being new. In some religions, virginity is seen as being of the body, such that when it is lost it can never be regained. But though there’s a spectrum of opinion within every faith, I believe that in Judaism, virginity is seen as something of the mind, and something, therefore, which is subject to continual renewal. We can always become mental virgins. We can wipe our minds clear and free of the ghosts of lovers past that haunt us, and we can enter into new relationships as if it were the first and only relationship. That is now what you must do.

 
If you make the mistake of bringing up some of your previous relationships with men, even in an effort to be more honest and authentic with your boyfriend, who may indeed become your husband, then you are making the mistake of re-experiencing those relationships rather than choosing to be a mental virgin. Repentance and renewal are essential, not just in religion and spirituality, but in human relationships and in human living. You have repented of your past. Now forget it and let it be, and let us not discuss it again.

May G-d bless you always, and I hope that your relationship with your boyfriend turns into a healthy and wholesome marriage.

With every best wish,
Rabbi Shmuley Boteach