Dear Rabbi Shmuley,
I am in a relatively new relationship (2 months) with a wonderful man who I'm developing strong feelings for. I've had a lot of unsuccessful relationships in the past, and I want this one to go right. My question is, how much should I share about past relationships, and when? For example, I'm divorced, which is something that my boyfriend knows. But he doesn't know that my ex-husband was unfaithful to me, and many other details of my marriage and other past relationships. Can I disclose things like that to him without seeming like I'm testing him next to these other men? When is the right time to share the "biggies" of your life, both good and bad?
--Ready to Talk

Dear Ready,
Two months should not be considered the early stages of a relationship. You are well into it by now. And you have to open up.

One of the major problems affecting modern relationships is that people cannot communicate. They are too inhibited, too afraid, or even too bored. Emotional openness, as expressed through intimate conversation, is a cornerstone of every good relationship.

You have been scarred in the past. So you need to do it right this time, and not bury your experiences and feelings.

Tell your boyfriend you want to share something important with him. Tell him that you love him and care for him. In the past, a man who you felt similarly for hurt you to the very core by cheating on you. Admit that as a result you have had major trust issues. Tell him you know it’s a fault born
of a scar, and that you are trying to heal yourself of it. Nevertheless, you wanted him to know, not because you suspect him of cheating. You know that he is an honorable man and would not do that. Rather, you are telling him so that if it ever seems that you are slightly closed, he’ll understand why.

Tell him also that you know this not an excuse for emotional distance, and every person has to work on transcending their painful experiences in order to once again become whole. Nevertheless, you wanted him to know about this piece of your past, just in case he translated your reticence as rejection.

Now, coming back to you, you can’t be in a relationship that is governed by fear. Stop being afraid of being yourself. You’ll never be happy, and you’ll sabotage a good thing with your boyfriend in the process. You have to learn to be comfortable with things that are on your mind and not be afraid to share them.

By the same token, you can’t make the mistake of judging one man by your experiences with another man. Not every guy is a jerk. Not every person is untrustworthy. You have to recapture your mental and emotional virginity, entering each and every relationship as if it is totally new.

Remember, your physical virginity can be lost. But the purity of the mind and heart can always be regained.

Rabbi Shmuley
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