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Want to Be a Dating Mentor?

Do you want to be more helpful to Jewish singles you know? 
Learn what it takes to be a dating mentor

By Rosie Einhorn, L.C.S.W. and Sherry Zimmerman, Esq.

Dating's Not Easy

Dating has changed significantly in the past quarter century. A life stage that seemed natural and relatively painless has become stressful for everyone and difficult to navigate for many. If you aren't a single adult, or a parent of someone of marriageable age, you may not realize how challenging it is for many marriage-minded men and women to find the right person and build a relationship that will lead to marriage. The dating experience is filled with anxiety and pressure, even for people who are able to find their spouses after a relatively short dating process. Those who date longer have to deal with feelings of frustration, rejection, diminished self-esteem, and fear that they will not be able to achieve the goal or marriage.

Most of the men and women who struggle with the dating process are bright, personable, functional individual who can use a good dose of emotional support and guidance. “Dating mentor” is the title we use to describe someone who can fill that role.

What is a Dating Mentor?

The best dating mentors are people who have a very positive attitude toward marriage in general and toward their own marriage in particular, and are willing to offer their listening ability, time, insight, and suggestions to daters who don’t want to handle dating on their own. Mentors should be mature, compassionate, perceptive, and non-judgmental, have an ability to relate well to other people, and desire to help singles on a voluntary basis. Because the dater needs to hear from someone with a perspective about dating and marriage that’s different from their own, we usually recommend that a mentor be a married individual or couple, or a widow or widower.

A mentor's primary "role" is to be a wise friend and coach for someone who is dating. She's the person the dater can talk to about his expectations, concerns, and experiences; she's the "address" he can turn to before or after a date. She'll listen to someone's doubts, hopes, and hesitations, and can offer her own observations and advice. The mentor provides encouragement when the dater feels discouraged, acts as a pair of glasses when the dater's view is blurry or distorted, and is a sounding-board when he needs to vent. The mentor is a hand-holder for a single who feels anxious or frustrated, and a cheerleader when there is happy news.

Sometimes, a mentor will help daters understand and clarify what they are looking for in a future life partner. He may help single clients build a network of contacts who may be able to introduce them to well-suited dating partners. A mentor can give pointers on where to go, what to do, how to dress, and what to talk about to someone who is new to dating or is finds one of these areas to be challenging, and can even offer to guide the single through a "dress rehearsal". A mentor might encourage a dater to set aside rigid expectations, be more open-minded, go out on a second date, or allow emotional connection or attraction a little more time to grow. A mentor can also help a dater recognize unproductive dating patters or spot red flags that arise during a courtship.

Getting Started

Most people become dating mentors by stepping into the role, even if they’re worried about not having all of the answers. Often, married people who have single friends are in an excellent position to be mentors. Or, they may have a special reason for wanting to reach out to daters - our friends Daniella, Lisa, and Michael each married late in their thirties and wanted to help other long-term daters they know succeed in meeting and marrying the right person. They live in different cities and neither knows the other, but each draws upon their own experience, and the experiences of their friends, to help single men and women. Other mentors develop good relationships with singles through their careers or avocations. They may be youth leaders, rabbis, guidance counselors, high school and seminary teachers, and people involved in community education programs.

How do you get started? You can take the initiative by approaching a single person you know and offering to share your insight. Mrs. Rosen, who was considered the "wise older woman" in her neighborhood, became Hillel's mentor after she telephoned him to explain, "I've seen you date many women over the past several years, and none of those relationships ever went anywhere. I've been told that you have started to see the daughter of an old friend of mine. I'm very fond of this young woman, and I think that the two of you may be very good for each other. I don't want to see her get hurt if it doesn't work out, and I don't want to see you go on another round of unsuccessful dating. Why don't you call me up after each date and we can talk about it? Maybe my perspective can be helpful to you." And it was – Hillel and the young woman have been married for several years.

A man we know helped two relatives get married after telling each one, "I wanted to be able to help the people I love get married, and so I went to a workshop on dating mentoring. I've learned so much – will you let me share it with you while you are dating? I think that once you know what I've learned it will be a lot easier for you to find the right person." Another woman never told her still-single best friend that she was mentoring her. She simply did what she always did – listened to her friend talk about her dates and gave her feedback. However, this time she added the insight she had gained by asking us for suggestions and by reading the books and articles we recommended.

Sometimes, it is the daters who find the mentors. Some people seem to "attract" singles who seek their advice because they are wise and insightful. Rivka is in her sixties, but many of her adult granddaughter's friends have been confiding in her since they were in high school, when they often accompanied their friend to her savta's home after school. She has learned a lot about the issues that young women deal with today and uses this information to advise many of these twenty-somethings through the dating process. Seminary and yeshiva teachers are often asked to become mentors for their present and former students.

What a Mentor Needs to Know

We’ve seen from our own experience that mentoring is a learning process. Although insight, common sense and good interpersonal skills are the hallmarks of a good dating mentor, the more knowledge an individual has about the issues contemporary singles face, the more effective a mentor he or she will be. You can find valuable information in books and articles about dating that have been written by people with a proven track record for helping singles.

Prospective mentors can read some of the books that advise singles how to prepare themselves for dating (Gila Manolsen's Head to Heart and our book, Talking Tachlis. Shaya Ostrov's The Inner Circle, Lisa Aiken's Guide To The Romantically Perplexed, Yaakov and Sue Deyo's Speed Dating), and Leah Jacobs and Shaindy Marks’ Shidduch Secrets have valuable pointers about the dating process itself. John Gray's Men Are From Mars, Women are From Venus and Mars and Venus on a Date provide information that will help singles understand the opposite gender.

Our book, In The Beginning, can help you answer many questions asked by singles who are engaged or may be on the verge of engagement. And the archives of our column, "Navigating The Dating Maze", and other writer's articles on dating at also provide a wealth of information for potential dating mentors to drawn upon.

You can build on that basic knowledge by examining your own life experiences, learning from your own clients, and learning from the experiences of others who work with singles. For example, the two of us draw on our experiences as therapists and as a family lawyer. We also apply what we observed when we mentored other daters – the suggestions that worked best for them as well as the insights they came up with on their own. We also brainstorm with professionals who are involved with singles on a daily basis, such as Jewish educators, matchmakers, teachers, rabbis, and community leaders.

One of the best ways to acquire a wealth of information about mentoring is by attending a Sasson V’Simcha dating mentoring workshop. These three hour programs on basic mentoring skills and advanced skills are crash-courses on the dating process, how to guide singles through each stage of dating, how to develop the skills effective mentors need, and how to resolve the questions and issues that often arise during courtship. People who participate in the workshops can supplement their knowledge by reading the articles and books referenced in their materials and by calling on us for ongoing "technical support".

Sasson V’Simcha’s “tech support”, and our encouragement, are also available to mentors who have not been to one of our workshops. If you’ve decided to become part of this valuable undertaking and feel you can benefit from our experience, or if you want to share your own success insights or successes with us, please contact us.

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