Q: I’m about to get married to the woman of my dreams. She knows I was married before; what she doesn’t know is that the marriage broke up because I was a schmuck. Ethically speaking, how much do I need to tell her?
You have a right to privacy, but a relationship that begins with massive deception has little chance of long term success.
Even JDate, where people routinely avoid exposing their dark side, suggests that profiles include a response to the question, "What I’ve Learned from Past Relationships." If the cause of your failed marriage somehow never came up before, at the very least, you and your fiancée should come to a mutual agreement as to whether sordid details of all past relationships are off limits.
But it would be much better to come clean. There are many shadings of schmucky behavior in marriage, ranging from rape to refusing to put down the toilet seat, but anything resembling either cheating or domestic violence would be relevant enough to warrant full disclosure.
It is true that once a person has repented from past transgressions, he deserves the chance to move on. The Talmud states (Yoma 86b) that it is enough to confess for a given sin on just one Yom Kippur and not the next. And Proverbs compares the person who continually dwells on past errors to a dog who returns to its vomit. A pleasant thought.
But for Maimonides, the only way to assure that repentance will stick is when the perpetrator is put in the exact same situation once again and is able to conquer his demons. That means that you’ll be on Jewish probation until you’ve been married to this woman long enough to wake up next to her and not be so dreamy-eyed. How will you respond when she barks at you for the umpteenth time to take the garbage? Or when you run into that pretty babysitter in the drug store and she asks for a ride home? Or when the woman of your dreams pushes your nuclear button by informing you that she friended your ex on Facebook and has heard all about your past? How will you react?
Life is sometimes unfair, especially to those who bear the burden of having harmed others. But it could be worse. You could have been the victim of said schmuckiness. That pain may never go away for your former spouse, while you will likely have no problem moving on.
But only if you come clean now. That involves lots of personal soul searching even before talking with your fiancée. If you truly love her, you both will need to know, beyond any doubt, that you’ve changed. So spill your guts. If you do, my bet is that your confession will bring your relationship to a deeper level. If it doesn’t, it may be time for someone to apply the brakes.