Dear Matchmaker Rabbi:

My ex-fiance is in jail, partially as a result of crimes committed against me and partially as a result of crimes committed before we met. At some point before we married, I figured out that he was responsible for my identity theft problems, that he had a criminal history and that he was married.  It was shocking because he was very loving, responsible, seemingly honest and such a welcome part of our family. Dealing with this was a nightmare and there was a lot of drama. I am trying to move on and leave it behind me, short of occasional legal issues I have to deal with (e.g., testifying as a witness in court). 

How much of this do I reveal in future relationships and how soon? This situation defines and reflects upon him and not me, but it is so bizarre and outside of most people’s idea of normal. I don’t want to scare anyone away.


Dear H:

Wow, you have really been put through a lot!

I agree that this isn’t something you should reveal right away — not because you have anything to be “ashamed” of but because, as you have observed, your experience is pretty far outside the realm of what most people know. Until a person gets to know you, and trust you, a date might wonder what role you maybe had in everything.

The “good” news — and the piece you should try to keep in mind — is that many folks have had relationships with troubled people. Most troubled-exes aren’t in jail, but they are addicted, they are medicated, they’ve lost custody of their children, etc. etc. There are a lot of skeletons rattling around in a lot of closets out there!

If I were you, I would be honest, but very brief in what I said about this guy until I  entered into a relationship with someone. You can say things like: “I was engaged once, but I found out he was a liar and a cheat, and it was a very painful situation for me and my family. So, we never married.” If the person presses for more, simply say: “I’d be happy to tell you more at some point in the future, but honestly, it’s behind me now and I don’t want to dwell in the past.” The important thing is not to sound defensive, or like you are hiding something … but don’t get bogged down in details either.

I think the same kind of circumspection is needed for people who are divorced,too. If you have ever been out on a date with a guy who is divorced, you know that the last thing you want to hear on the first or third date is some long blow-by-blow explanation of what happened to the relationship and why it ended. To know he was married for X years, when it ended, and a very brief statement as to “why” is really all you need.

Once things are intimate, physically and emotionally, that’s the time to start dusting off the ol’ skeletons. A month into things perhaps? Or two? It all depends on when you feel like your new boyfriend has started to understand the real you.

– The Matchmaker Rabbi

Joysa Winter, aka The Matchmaker Rabbi, knows all about how hard it is to find lasting love. It took her 17 years to find Mr. Not Wrong! In that time, she tried just about every singles site, dating club and Matzah Ball known to humanity. Now a rabbinical student and the mother of 2 young kids, nothing brings her greater joy than officiating a wedding. She is finishing a book on her dating misadventures called Chasing Cupid, Tales of Dating Disaster in Jewish Suburbia. Read more about it at
One Comment
  1. Why do you want to tell your dates about your ex? Do you still have a relationship with him? Have you children and some legal mess?

    If not, you need not ever say anything. Don’t think about your ex and don’t talk about your ex. Don’t speak with your ex ever again. You need to let him go to the dusty history book shelves. Remember, that was a different you. Like Elvis, she’s left the building.

    If you have a legal relationship with your ex. Tell a person on your second date. If you have have a third date, it likely doesn’t matter to the person.

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