click here to jump to start of article
Join Our Newsletter

Get latest articles and videos with Jewish inspiration and insights​

Dating Advice #134 - Dating Mentor
Dating Advice 134

Dating Advice #134 - Dating Mentor

How the participation of a third party can help facilitate one's getting to the chuppah.


Dear Rosie & Sherry,

In some of your articles you speak about the advantages of having a dating mentor. Can you also tell me a little more about this new approach? Who can become a dating mentor? And how does somebody find a mentor that's good for them?


Dear Julie,

Thanks for writing. This week we conducted a workshop to introduce 25 men and women to the concept of a dating mentor. These participants, almost all of whom were married, wanted to know what mentoring singles entails, because each of them knew of friends, students, neighbors or family members who were disappointed with the manner in which their own dating was progressing and wanted to help them.

Some people cannot understand why we recommend mentors. They figure that people should be able to date successfully and get married on their own. Most of our readers know that society is a lot more complicated than it was a few generations ago, and that a large percentage of single men and women don't see enough models of successful courtships to figure out on their own how to go about getting married, and especially how to use courtship to develop a relationship that has all of the ingredients for a good marriage. A dating mentor can be a big help in this regard.

A dating mentor is a man or woman who is willing to be a combination friend/coach/advisor and sounding board for an unmarried person. We believe the best mentors are people who are or have been happily married, are genuinely concerned about helping someone else, have good insight into other people's personalities, can be objective and can refrain from imposing their own expectations on someone else, and are straightforward with others but know how to do so in a caring and considerate manner.

We recommend that people who are interested in working as mentors familiarize themselves with the issues that single men and women regularly confront. The following are just some of the books that can be very helpful to someone who would like to mentor: our books, "Talking Tachlis" and "In The Beginning"; Shaya Ostrov's "The Inner Circle"; Gila Manolson's "Head To Heart"; and John Gray's "Men Are From Mars, Women Are From Venus."

While the two of us conduct training workshops that have been very helpful for people who would like to be dating mentors, it isn't necessary for someone who wants to mentor a single to attend a workshop. And, whether or not someone who is serving as a mentor has attended one of our workshops, if he or she has some general questions or wants guidance on handling a particular situation, we're happy to discuss it with them by e-mail or by telephone.

There are as many ways for a mentor and a single person to work together. A single guy who has been dating unproductively for a long time and may finally have met someone who seems to be right might want guidance and encouragement. He may ask, "How can I tell that we're right for each other?" "How do I know I'm really ready to get married?" "When will I know it's the right time to talk about marriage?" "I really like the person I'm seeing, but I have seen some of my friends get divorced and I worry that the same thing might happen to me. I need to talk this through with someone."

Or, a woman might consult with a mentor because she's concerned about something that is happening in her courtship and she doesn't know how to resolve it on her own. Maybe she's begun to feel that the man she's dating is a little controlling. Or things could have been going well with the man she's dated for several weeks, but suddenly she feels ambivalent. A dating mentor can help her sort out what's really happening.

She may be experiencing anxiety because she realizes this man might be "the one" and she's starting to panic. Or because the two of them have been seeing each other almost every day and her emotions haven't had the time to work themselves through. Or because the infatuation she felt in the beginning is starting to wear off and now she's seeing aspects of her date's personality that she isn't sure she can accept. A dating mentor can assure her that these feelings are normal, are not necessarily a sign that anything is wrong with her courtship, and guide her on sorting out what is at the root of her anxiety.

Other singles might seek the advice of a mentor if they seem to be repeating one or more unproductive patterns with several dates -- e.g. never getting past the second or third date, sabotaging the courtship just when it seems to be going somewhere, gravitating to men/women who are always emotionally unavailable. This necessitates someone to help understand why this is happening and to give ongoing guidance in the future.

Some mentors prefer to work with someone they already know; others like to develop friendships with new people. They may invite their clients out for coffee or to their homes for an occasional Shabbat. Other mentors are happy to simply give advice over the telephone or during short, face-to-face meetings.

Mentors may have to serve as hand-holders for singles who have developed a wonderful relationship with someone who is right for them, but need positive reinforcement and encouragement to help them decide to become engaged… get through the normal anxieties and stress of engagement… distinguish between pre-marriage jitters and genuine problems with a potential spouse… and even survive a few bouts of cold feet and make it to the chuppah.

We suggest that marriage-minded men and women who would like a dating mentor should approach someone whose judgment they trust, and who appears to have a good marital relationship (or who is widowed after being happily married). You can explain the concept of a dating mentor, and ask if the person would be willing to work with them in that capacity.

We hope that this information is helpful, and we wish you the best of luck.

Rosie & Sherry

August 23, 2003

Submit Your Dating Advice Question (Click here)

Give Tzedakah! Help create inspiring
articles, videos and blogs featuring timeless Jewish wisdom.
The opinions expressed in the comment section are the personal views of the commenters. Comments are moderated, so please keep it civil.

Visitor Comments: 3

(2) Elisheva, August 29, 2003 12:00 AM

Great, but...

The theory of a dating mentor is a great idea, but many married people I know are not sensitive to the experiences single people face, or are not happily married themselves. Single people can be very vulnerable and an untrained mentor can do more harm than good.

It would be helpful if there were a more structured program for Jewish singles' mentors in this regard, with specialized training and actual contact information of mentors. I am sure many singles would be grateful for this and it would be a great mitzvah and form of tzedakah or volunteer work. At the least, I am sure some singles would even offer to pay for some of this type of coaching (though not much - many singles support themselves).

Perhaps one mentor can also stretch their availability by assisting several singles at once via email, telephone, or group sessions.

I think your columns are terrific, but your concepts need to be implemented with actual "hands on" experience.

Marriage Minded Mentor, April 2, 2012 4:32 AM

Marriage Minded Mentor are on the way

Elisheva, you are in good company. I have heard your plea many times from many singles. I aspire to train a team of mentors but it's going to take a little time to get it off the ground. This post is old, so i'm hoping you're happily married and a sensitive mentor to the singles you know!

(1) Anonymous, August 28, 2003 12:00 AM

I have mentors

I already have dating mentors. I call them friends. Don't other people have friends, too? Why does everything need to sound so formal and structured? The next thing you will be telling me is that people should pay for the services of a dating coach.

Submit Your Comment:

  • Display my name?

  • Your email address is kept private. Our editor needs it in case we have a question about your comment.

  • * required field 2000
Submit Comment