Shalom Rabbi,

I am a 53-year-old woman and have two wonderful sons (ages 16 and 21) who live with me. Two years ago, after 28 years of marriage, my ex and I divorced. We have done a really good job of staying good co-parents and I believe have shown our sons how best to resolve conflict with honor, caring and love.

I have recently started dating, and though I’m not even close to thinking about marriage, I do miss the wonderful joy of connecting to a man. I am ready for a committed relationship.

My question: It has been over thirty years since I have dated and things have changed a lot. Is it appropriate for me to contact a man that I first notice on JDate? Or does that send the wrong message?

Thank You!
-Confused In Colorado


Dear Confused,

I am sorry to hear about your divorce. Having been through that myself, I always say that even when it is the best choice, it is difficult. How wonderful it is that you and your ex-husband have set a good model for your sons.

One of nice things about JDate is that you are free to contact anyone of your choosing. This is true for men and for women. It is completely appropriate for you to send a communication to a man signaling your interest in connecting. I would suggest by starting with something brief – a hello and a reference to something in his profile that caught your attention. One or two sentences would be plenty to begin. If he is interested, he will get back with you and you can take it from there. If you don’t hear back, then you can move on. It is also fine to send a communication to more than one man at a time, as we never know which connection will evolve.

I wish you success in your endeavor of finding a loving relationship.

To ask Rabbi Damsky a question, email

Rabbi Robin Damsky is the spiritual leader of West Suburban Temple Har Zion in River Forest, IL,, and is co-author of Find Fulfill Flourish, a book to help you find a life of meaning, purpose and fulfillment, at


  1. Sharon Doniger

    I am a widow who was married for 34 years and I too am trying to navigate the dating scene. The things you wondered about are also the things I wonder about. Is it better to send a note or should you send a flirt?

  2. Jonathan Angress

    As a 24 year old male and someone who may not be too experienced in dating, but definitely knows what the current fads are…especially among high schoolers and new college students (I have a 16 year old sister), I can tell you that many women still prefer the traditional approach of a man initiating contact and making the first move. At the same time, there are just as many women out there who have no problem contacting a man first, or asking a man out, or even initiating a first kiss.

    With that being said, as a younger male, I can tell you from experience that I definitely prefer when the woman makes the first move. Men are extremely insecure, even though they put on a front of being confident and sure of themselves. The truth is, men would definitely like it if women made the first move.

    I should mention that perhaps my words should be taken with a grain of salt. I am not a normal 24 year old…I tend to be an old soul and traditionally minded in regards to a select few things. As a result of this, I tend to be attracted to women who are quite older than myself (30+).

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