About five years ago, Mrs. Goldbaum found herself turning away five clients a day, simply because she had no more time to give them. She started training others in what she calls her Directed Dating Approach. To date, Rochel has trained about 75 dating mentors. These women likely represent the first generation of paid dating mentors in the field.

Still, why is it that singles relied on shadchanim alone for centuries, but in today’s era, so many people are seeking outside eitzah that a “dating mentor” is now a career path?

With shidduchim an undisputed “crisis” in today’s day, shadchanim sometimes put pressure on singles to move things forward, but, as Mrs. Goldbaum stresses, “Pressure and desire don’t coexist.” She states that one of the most important jobs of a mentor is to shield the single from pressure. “It’s very hard to have a desire to marry someone if you’re feeling pressure to make a decision. A single will often decide that he or she wants to stop dating, not because the person they’re seeing isn’t right for them, but because they just want to end the pressure. I’ll tell a girl, ‘You’re going on three more dates, no matter what. And for the next three dates, you’re not allowed to decide anything.’ Without fail, the girl is calling after the second of those dates asking, ‘Mrs. Goldbaum, is it okay if we get engaged now?’ All she needed to feel her innate desire was to take the pressure off.”

Another important difference between a shadchan and mentor, stresses Mrs. Goldbaum, is that while a relationship with a shadchan often ends when a shidduch does, a mentor can be there for the single throughout the entire parshah. “I tell my clients, ‘The goal is not for this particular shidduch to work. Rather, right now, you are learning about the other person, and he is learning about you, and you’re looking for clarity.’ That helps to keep singles calm and focused,” and the process can progress.

Mrs. Dina Schoonmaker, a relationship counselor, popular lecturer, and senior staff member of Michlalah Jerusalem College, agrees. “I’ve been saying that dating singles need mentors for the last twenty years, and I’m glad to see it’s finally happening,” she says. “Honestly, I think it would be great if every single had a mentor. Many daters are reluctant to share sensitive information with their parents for fear that if the shidduch is successful, their parents will retain a negative opinion about the spouse. Other times, they’re afraid that the parents will respond very strongly to something and encourage a breakup, or conversely, push them to continue. It’s good to have an objective party in addition to the parents, especially when there’s sensitive information that you want to hash out with somebody.”

On the other hand, Mrs. Miriam Lipson (formerly of Providence, Rhode Island, now in Baltimore, Maryland), a high school teacher of four decades and shadchan for almost as long, compares the current phenomenon of “dating coaches” to the all-around indulgence of today’s generation. “The same way we have party planners nowadays, when we used to make much simpler simchahs on our own, this is just another way of raising the bar,” says Mrs. Lipson. “Of course, there are situations when someone truly needs a mentor, but often anyone with daas can help a single through the process. That it’s become unthinkable to date without hiring a mentor is another symptom of the excess of our dor.”

Mrs. Rachel Burnham of d8gr8 (see sidebar) sees it differently. “The same way we didn’t have OT and PT and all the specialists we have today, this was also always lacking. People just didn’t get the help they needed, and some ended up in disconnected marriages because of it.”

In years past, mentoring a single through the shidduch process was either done by parents, a shadchan, or by a kind high school teacher, seminary teacher, rebbetzin, or the like.

“I was guiding former talmidos and my husband’s talmidim through a shidduch long before the concept morphed into a fee for service,” Mrs. Lipson says. Recently, singles whose shidduchim she is not involved with as shadchan have begun reaching out to her. “Some people worry that the shadchan is too involved to be objective, so they’re less likely to accept what she has to say. Parents and their children feel they need an outside opinion because they’re so emotionally invested and the situation can get very charged. They want ‘fresh eyes’ to help them gain clarity. I’m always happy to help,” says Mrs. Lipson, but she emphasizes that while many people assume the shadchan has an agenda — and therefore prefer having a coach on board — she and the shadchanim she is involved with do not “push” shidduchim.

And there’s more. Chava, an experienced shadchan, is wary about the overuse of dating mentors.  “First, I want to thank the people out there who have made it a priority to help our young women in shidduchim. You’ve truly made an impact on the klal, and we’re all grateful.” But there’s a part of the picture you may not be seeing, she says. “My job as a shadchan is to see the whole person, and whether or not something proceeds toward an engagement or just lasts a few dates, I speak carefully with both sides in a focused, deliberate process that takes both the individuals and the pair into account.”

What mentors don’t realize is that by coaching only one side, they can majorly derail a shidduch. “The shidduch process involves both the girl and the boy. You cannot possibly give advice based on hearing only the side of the girl who came to you for eitzah. While the coach’s insight is always well-meaning, and often spot on, there are two sides to every shidduch. Had the coach heard the other perspective, known the personality, receptiveness to guidance, and the way the shadchan is guiding him, they might have guided their client another way. When you’re only dealing with one side, there is a huge part of the picture that you are simply missing,” Chava says.

All in a Day’s Work

Leeba Bernbaum*, a mother of three married couples, never hired an official dating mentor for her children. One of her daughters was blessed to have a high school mechaneches who mentored her throughout the dating process. “She gave both of us such clarity. Her advice was so on the mark, and she stayed with us until the shidduch became official. When my son was dating, I spoke to a mentor of mine for my own clarity. She was a tremendous resource for me when I was ready to throw in the towel. Even though I got lucky and wasn’t charged (I gave her a nice gift), I think paying for someone’s time is a positive thing because it helps someone stay focused on you. Like a therapist, you need to do your research and make sure it’s someone you can trust, but I think it’s a very important resource for girls and for boys. Not always can he reach his rebbi when he has a question about whether he should continue, or if they’re not feeling what they need to be feeling.”

So maybe mentors have always been necessary, but now we’re just willing to pay for it? What are we paying for, though?

The dating process can be compared to a staircase, with the role of the mentor as the banister, according to Rochel Goldbaum. “There should be a certain progression in dating. For example, the first date is like a Shabbos table conversation, and the same way you wouldn’t share your deepest thoughts and feelings as a guest at someone’s Shabbos table, you wouldn’t expect that on a first date. But as dating progresses, you want to make sure you’re opening up more. A mentor’s job is to be the banister — to make sure you’re steady on each step, and you don’t skip any steps on the way.”

Some singles need extra help with relationship skills, like how to communicate well, bring up sensitive topics, and deepen or expand conversations. Others need help with clarity in the dating process. “They may need help learning how to trust their feelings, rather than relying on someone else’s opinion, or gaining the confidence to say no when necessary, and yes when there’s potential, even if they’re nervous,” says Mrs. Goldbaum.

“The most common calls I get are panicked ones from mothers of engaged girls,” Mrs. Goldbaum continues. “They tell me, ‘She’s not sure she likes her chassan’ or ‘She’s just not excited.’ After I’ve established that the boy has the qualities necessary to be a good spouse, I try to figure out what’s holding the girl back. Most often, she’s skipped what I call the ‘heart stage.’ The couple hasn’t really shared emotionally with each other — their feelings, their dreams. They haven’t been vulnerable. If there’s time before the wedding, I have them redate each other. Eighty percent of the time, they go to the wedding feeling great; twenty percent of the time, they break it off. But it’s never too late to redate. I’ve worked with couples to redate who have been married for years already.”

As a mentor, Mrs. Goldbaum does a lot of reassuring. “I also do a lot of ‘erasing’ of the image that a single has of what he/she thought she would marry. If I had five dollars for every time someone told me, ‘This isn’t what I imagined,’ I would be a wealthy woman. Many, many potentially great shidduchim will fall through if someone can’t move past their preconceived image of who they thought they’d marry.”

She shares an example. “Recently, I was working with a bochur who thought he would wind up with a younger girl, on the quiet side. He ended up dating a girl a couple of years older than him, who was outgoing, confident, and assertive. They got along really well and the dating progressed beautifully, but it was hard for him to erase the image he had in his head, and he needed ‘permission’ to leave the image behind and appreciate the girl in front of him. So we worked through that together. Now they’re happily married.”

“When I deal with singles, I ask them to answer two questions,” says Mrs. Lipson. “What do you want? And how do you intend to get there? The most common answer singles give to the first question is: ‘I want clarity in decision-making.’ But my question is multidimensional. I want to know: What do you want in life, in marriage, in this relationship (if you’re currently dating), and what do you hope to gain by talking it over with me?

“The first question compels the person to think and to articulate her feelings, dreams, and desires, which then provides her with the ability to answer the next question: How do you intend to get there? Once singles can express this clearly, they’re empowered to listen to their own voice. So while, yes, there is an older, wiser, more experienced person in the background, the ultimate decisions they make in life are their own.”

The “Other Side”

Rabbi Tzadok Katz, one of BMG’s famed shadchanim, agrees that many of our young men would benefit from talking to a dating coach for one or two sessions. They’re not used to talking with girls who aren’t their sisters, so they might need a little polishing up. But, he cautions, not everyone is qualified to hang out their coaching shingle. Simply taking a course and becoming “certified” is not sufficient to understand the nuances of the shidduch process and how it can play out in real life.

There are a number of prerequisites to being a good coach, he says. “A person has to be experienced. But not just experienced in relationships — experienced specifically in shidduchim. Some people think dating coaches are almost therapists. They’re not. The goal of dating is not to develop a relationship with the other person, it’s a vehicle to see if two people are compatible for marriage. Shidduchim have a completely different set of rules from therapy. For example, a client in therapy is encouraged to put everything on the table (‘the whole truth saves everyone a lot of time’). That isn’t the case when a boy and girl are trying to determine whether or not they can build a relationship. Discussing one’s issues is not necessarily advantageous in shidduchim, because that is missing the point of the dating process. There is also a logic behind therapy and reasoning, which does not necessarily exist in shidduchim, where there can be an attraction that can’t be explained in logical terms.”

That leads to Rabbi Katz’s second point. “These coaches must be experienced in shidduchim, but not just generally in shidduchim — they have to come from the same circles as the person they are coaching. This sounds like it shouldn’t be a chiddush, but it is. The whole concept of dating is different in chassidish circles and the yeshivish community and the modern world. Questions like how deep the connection should go while the couple is seeing each other and what level of interaction should they have, will vary from community to community. If your coach is not from your community, he or she will be advising you toward a goal that doesn’t align with the dating process. I once had a boy who was advised by his mentor to say something that was wildly inappropriate in his circles. Not only did it destroy the shidduch, it also damaged the young man’s reputation.

“And this is not limited to hashkafah,” Rabbi Katz continues. “If the coach lives in a very out-of-town community, they may not understand the culture of an in-town shidduch, which can be a problem for the client.”

To that end, Mrs. Lipson recommends that people don’t dismiss the shadchan-as-coach just yet. What a shadchan can bring to the table that a mentor can’t, is an overarching view of the situation. “As a shadchan, I’m clued in to the other side’s perspective. When I redt a shidduch, I am actually coaching both the boy and the girl. The difference is that I’m coming at it with the knowledge of the ‘other side.’ For example, in one shidduch I made, the girl’s side was concerned that the boy was a little tightfisted. She’d gone out with a number of other boys and was accustomed to being taken out to eat. Her current date, on the other hand, brought snacks in the car.  As a mentor, I’d only be able to work with the information given to me by the client, and we might have to twist ourselves into a pretzel or get into awkward territory to determine whether or not the boy is truly tightfisted. But as the shadchan, I’m not working in that same vacuum. In this case, she was his first girl, and I knew that his sisters had warned him that girls didn’t want to go out to eat until they were super comfortable and almost ready to get engaged. It didn’t take more than a minute to allay her fears — and he took her out to eat on their next date.”

So is that a no for mentors?

Not at all, says Rochel Goldbaum. “Times have changed. We’re in a digital age now, and that has brought a seismic shift to the world. People are so exposed, even in relatively sheltered homes. Our worlds have gotten so much bigger — we’re exposed to so many more people, which gives us a much bigger range of ideas about what’s out there. And the more choices you have, the harder it is to make a decision.

“It’s not just that,” Mrs. Goldbaum continues. “We’ve become very image-based and a lot less idealistic. Anxiety has skyrocketed. Girls are confused about what they want and don’t realize that so much of what they’re seeing is just superficial. Relationships thrive on real, but the world has become a place where people are petrified to be real. People are so busy cultivating a safe image that sometimes they’re not even sure who they themselves are.”

Still, “not everyone needs a mentor,” argues another shadchan, who prefers to remain anonymous. “In my experience, it’s mostly older girls who need them, and I’ll explain why. In the secular world, high school girls learn to evaluate themselves based on how boys see them. We mostly avoid that in our world, baruch Hashem, but when a girl spends a long time in shidduchim, she may start to question her worth and see herself as less than. Her self-image shrinks down to how she imagines boys view her. She may need a mentor to undo the damage of years of dating to restore her belief in herself and to trust her own judgment.

“Unfortunately, there are now nineteen-year-olds whom society has convinced that they aren’t good enough and already need that mentoring. But there’s nothing wrong with these girls. They’re wonderful and have everything to offer as wives and as mothers. We’re not talking about personality overhauls — just helping them remember their own worth so they can project that on a date.”

On the other hand, Rabbi Meir Levi of BMG has found that the dating coach “industry” often causes people to doubt their own intuition. “You’re creating a situation where young people are outsourcing their thinking to someone else. I know of coaches who help chassanim write letters to their kallahs. It’s so artificial. Then the couple gets married, and they actually have to go it alone and they realize… hey, do I even know/like this person? I think it can be argued that some of the young divorces are happening because of overbearing and unqualified coaching.”

To mentor or not to mentor, that is the question. And, it seems, there are no easy answers.

But everyone agrees that the best thing anyone can do for a single person — at any age and stage — is to inspire confidence. “The most attractive traits are positivity and confidence,” says Mrs. Goldbaum. “Anything we can do to make a single feel good about themself helps.”

Making of a Mentor

Rachel Burnham never planned on becoming a dating coach — the job chose her. After 14 years of dating, the then-34-year-old Rachel Avigdor married her husband. After so many years in shidduchim, Mrs. Burnham had been through a lot, including some broken engagements, and she was open to sharing with others her experiences as an older single.

“People started reaching out to me because they knew that I’d been through a lot in my dating years. I would tell all these older girls, ‘There’s nothing inherently wrong with you. You are marriageable,’ and they would literally have tears in their eyes. I was someone who had been there and I got them. I knew where they were coming from. HaKadosh Baruch Hu puts everyone where they need to be. For most of those 14 years I was dating, my husband was married to his very ill first wife. When she passed away, I was the first woman he dated.”

Once she was finally married, Rachel’s single years left her with a decent dose of “survivor’s guilt,” as she puts it. “I knew I wanted to help others, but I wasn’t sure how.” Then she started getting calls from women seeking guidance. “Those girls found what I said helpful and told their friends.”  In her experience, it wasn’t about getting more dates; the women she knew were going out, but they weren’t getting engaged. Sometimes people were stuck because of a trauma, whether their parents were divorced, or their childhood home wasn’t a healthy one, or they didn’t feel pretty or worthy. Often these women would self-sabotage really good opportunities, and they were met with rejections or would reject the men they were dating. I started my marriage in campus kiruv, so I was helping a lot of the students as well as others. These calls were taking up so much of my time that my husband encouraged me to launch my mentoring business, and d8gr8 was born.”

When she coaches, Rachel asks her clients, “Would you want to date yourself? Are you someone you’d be excited to date?”

“Many of my clients say no. They are looking for something they admit they don’t bring to the table, whether it’s simchas hachayim, solid hashkafos, a strong work ethic, or something else. That’s okay, we’re all works in progress, and this is what I’ll work on with my client.

“I tell my clients that there’s nothing inherently wrong with them that’s causing them not to get married.  But there are two paths in life. You can get married young and grow up together with your spouse, or grow into the person who can marry your spouse. I use myself as an example: Not only was my own husband married to someone else for most of my dating years, I also had to grow into the person that would be able to marry him.”

(Originally featured in Family First, Issue 915)