“I thought he was extreme,” she recalls with a laugh. “There was a part of me that felt, as a psychologist, that I better go rescue him, and there was another part of me that knew I had no idea about Judaism, and that, as a Jew, I should go explore it.” Off to Israel she went.

Her brother, thrilled that she actually came, introduced her to his rosh yeshivah, Rabbi Shimon Green of Bircas HaTorah, in the Old City. When they met, Jackie told Rabbi Green point-blank, “I hate religion.” He responded, “The religion you hate — I hate it, too. Now let’s talk about Judaism.” She was intrigued.

From there, Jackie attended Aish’s Discovery Program. She remembers being profoundly impacted when she learned that Jews were meant to be a light unto the nations. Growing up, she had never heard of that concept. “I had such a drive to elevate the world,” she recalls. “That’s what my whole secret life mission was. I had had no idea that was the Jewish mission.”

After Discovery, Jackie went on Jewel, and then ended up at Neve Yerushalayim.

She had suddenly gone from being a nationally respected talk show host, an expert in her field, to being at entry level. “It was very humbling to feel so inept, what with the Hebrew and everything,” she shares, remembering how she had to start from scratch, sitting in a room with 20-year-olds, all learning the basics of Judaism together.

As she learned and grew, she found that her professional success was no longer the most important thing about her life. “I found myself asking, ‘Who am I?’ ” she remembers. Without the roles and responsibilities she had had in Australia, Jackie was forced to dig deep into her fundamental understanding of who she was as a person, beyond her external achievements. “That was the best thing I ever did, ever, because it built me inside.”

Jackie chose not to mention her professional success during the first few years she was at Neve, and she recalls how it was quite the bombshell when she started telling people. Then she realized that sharing her professional success was something she could, and should, use in kiruv work. “It gave me instant credibility,” she noticed. And she also appreciated how her psychology practice provided a strong foundation for the work that she would eventually do.

Jackie continued learning full-time for five years. She was such an adept student that she eventually began teaching at Neve. After a couple of years of teaching, she accepted a position as an educator and program developer for Olami, the premier campus kiruv conglomerate. This meant she had to leave the hills of Har Nof for the skyline of Manhattan. It was a daunting transition. With the exception of a brief trip to the States when she was in college, Jackie had never been to New York. Now she’d be living there.

But she plunged right in. At Olami, Jackie developed kiruv programs, including a signature program for women called “Souled,” and traveled extensively to many of Olami’s 320 locations, especially after she took on the Director of Leadership Development position. “I was always everywhere,” she recalls, “and I absolutely loved it. It was amazing, meaningful, and fulfilling. I learned a lot about human nature and transformation from those experiences.”

“Why Are You Single?”

Throughout her time at Neve and with Olami, Jackie was dating. And dating and dating. She was doing all the normal hishtadlus with shadchanim, working on herself and getting hadrachah, but after over a decade of dating, she was still single.

It was a pain point in her life that was on a simmer until a fundraising meeting brought it to a boil. “I was running a massive leadership program, with 600 people, in Spain,” she recollects. They were meeting with someone for funding, and before the meeting, the COO of Olami prepped Jackie that the person they were meeting with, an Israeli, had a tendency to be very direct, and that he might ask personal questions. Would she be okay with that? Jackie remembers responding, “Yeah, yeah, I’m good, I love Israelis, I’m really direct, I can handle that.”

During the meeting, Jackie found herself answering the routine questions about budget and staffing, the hashkafah of the program, how it would help teach young Jewish professionals about leadership. Then the philanthropist asked her what she was doing about her own leadership. Oh, this is one of those personal questions, Jackie thought. She started listing some of the many things she was working on. But the potential donor interrupted her. “Why are you still single?” he asked.

At a loss, Jackie responded, “I don’t know. I really don’t know.”

He leaned forward, looked at her penetratingly, and said, “You have to go home today, and you have to tell Hashem, ‘I accept.’ ”

“Accept what?” Jackie asked, unsure where this total curveball of a conversation was going. He told her that she needed to accept that if Hashem decided that she’d remain single, she would accept His ratzon. Essentially, he told her, if she didn’t get what she wanted, she’d need to accept that reality. Not give up on what you want, he clarified, but trust Hashem no matter what He decides.

“It was the one piece I could not accept,” Jackie recalls. “I had given up everything for Hashem, I had been helping all His children for years, and here I was, still single.”

Understandably, this invasive conversation made Jackie extremely emotional. “It was a long meeting, and it ended up being all about me and my personal life. We didn’t even discuss the course we were seeking funding for.”

At the end of this interrogation, the potential donor said, “I like her, she’s real, she’s willing to take risks, I want to work with Olami.” Then he walked out of the room.

Mortified at her emotional state, Jackie apologized profusely. But the donor’s staff assured her that this was the best meeting they’d had in two weeks. Still, while the meeting had gone well, Jackie was left reeling from the emotional fallout of an intense conversation about such a painful topic.

The trip ended, and Jackie spent that Shabbos at the home of her rav, Rabbi Sholom Kamenetsky, in Philadelphia. There, she spent a lot of time thinking about what had happened. She asked herself what might be blocking her from accepting the challenge of singlehood. She started using one of the tools she’d learned and taught as a psychologist to reflect on a deeper level, and soon realized that, “I felt betrayed, deep down, and I didn’t want to acknowledge that, because I felt that it wasn’t okay to feel betrayed by Hashem. I was rejecting my reality.”

Feeling betrayed is a universal reaction to nisyonos, Jackie tells me. “We can know on an intellectual level that Hashem loves us, and we can be grateful for all the good in our life, and still feel like, ‘How could you do this to me?’ when it comes to a painful challenge.”

That Shabbos, four years ago, as Jackie continued to tune into her inner voice, she came to the additional realization: “I felt like if I didn’t get married, it meant I was a failure. I’d internalized the idea that remaining single meant I was less worthy than others.” Sitting with these uncomfortable feelings and realizations, her emotions raw from nearly a week of grappling with this issue, she decided it was time to stop judging herself.

Thinking of the mishnah in Pirkei Avos (2:4) that states, “Make His [Hashem’s] Will like your will, so that He will make your will like His Will,” Jackie resolved to accept that she was exactly where she needed to be at that moment, and that whatever Hashem decided she was meant to experience in her life, she would give it her all.

As a result of this inner work, she experienced a profound shift in how she felt about herself and her situation. She had moved her internal needle closer toward the acceptance the Olami donor had told her she needed to feel.

On Motzaei Shabbos, Jackie was having Melaveh Malkah with some friends. She shared the story of her crazy week with them, and they spontaneously decided to brainstorm potential matches for her. During that conversation, her husband’s name was suggested.

From the Inside Out

Jackie’s experience gave her a firsthand look at the power of our internal world and how much we cocreate our reality with Hashem. She saw how judgment (thoughts like, “If I don’t get married, I’m a failure”) and rejection of circumstances (“I don’t want this particular nisayon”) keep women stuck. She knew she wanted to help women in this area, and began coaching other women soon after she got married. Most of the women who work with Jackie are looking to increase their confidence, self-worth, clarity, and trust in their own decision making.

Self-confidence was something Gitty* had long struggled with. Having attended a school that wasn’t a good fit for her, hashkafically, Gitty had always felt like the odd one out. Due to the constant teasing and bullying she had experienced as a child, she was very self-conscious of not fitting in. As a result, Gitty subconsciously assumed that if there was a normal milestone her peers were reaching, she would not be included. When she came to Jackie, she was the only one in her class not yet married.

Using psychology tools — now coupled with Torah wisdom — Jackie taught her how to heal that inner child who was always left out, to internalize that she was exactly where she needed to be and who she needed to be, and reminded her that Hashem loves her just as she is. Gitty transformed self-rejection into self-acceptance. She went from having no dates to dating in a meaningful way. Now she’s engaged.

Jackie’s website describes her as a dating coach, but a more accurate description would be teaching women how to increase their emotional and spiritual intelligence so they can be open to marriage on a deeper level. It’s work she encourages women to do even before working with a more traditional dating coach.

“I love helping women at any stage of life connect to themselves and their purpose, but my course is for regular frum women over the age of 23 or 24 who are still dating,” says Jackie. “I see a big need there.” She’s spoken extensively with shadchanim who are seeing all these emotional challenges and don’t know what to do to help fix it. Jackie is in a unique position to not just give over crucial skills that can help, but to also validate women who are in so much pain.

There’s enormous pain that so many singles experience — the pain of not being seen, of not being respected, of not feeling like they have a voice, of feeling broken, judged, and of being recipients of too many insensitive comments. “All these things, I lived them,” says Jackie, “for so many years. There is something to that, I understand the pain.”

Having lived it, Jackie can tell the women she coaches with exquisite clarity that, “You can never know why you’re not married, you can never blame yourself. However, we do know that in any nisayon, you have to work on yourself, and you have to reflect, do a cheshbon hanefesh, but in a deep way, and on an emotional level as well.”

She tells me, “I’ve noticed that this kind of work seems to be the most overlooked. We develop our chesed and our relationship with Hashem, but it’s this crucial piece of working on our bein adam l’atzmo that I think can be profoundly impactful.

“The Talmud says we don’t see things the way they are, we see things the way we are, so it would follow that as we internally shift, we not only experience a different reality, but we attract a different one also,” she shares, mentioning that the book It’s All in Your Mind, by Sara Yosef, goes more into this topic from a Torah perspective.

Beliefs and Stories

Jackie explains some of the psychology behind her work. There’s a huge part of our brain that functions on a subconscious level, she tells me. Over 80 percent of our knee-jerk responses are reported to be from the subconscious, which is staggering when you think about it.

Any meaningful emotional experience we’ve ever had, pleasant or unpleasant, is stored away in our minds, like in a back filing cabinet. This is what informs our belief systems, things like “I’m likable,” “I’m good enough,” or, “The world is trustworthy.” Or, conversely, “I’m worthless,” “The world is a dangerous place.”

Our belief systems originate primarily from our childhood, and we view the world through the lens of the stories we tell ourselves based on our early experiences. Jackie says that part of our tikkun in this lifetime, what we’re here to correct and fix, are patterns that we keep generating through subconscious blocks by perpetuating these stories.

How does this appear in dating? One of the first things Jackie asks potential clients when they make a discovery call to her is, “What are your patterns for dating? What typically happens? Do you typically drop the guy? Does he reject you? Do you have no dates coming in?” She notes that the answers to these questions can give information about the subconscious patterns.

She gives the example of Shani,* who was rejected as a girl and has a belief system about not being loveable. Because of this subconscious block, her walls and defenses are up whenever she goes on a date.

Imagine Shani gets picked up for her date, and she sits in the car silently. Her date tries asking her basic, getting-to-know-you questions, and she responds with short, accurate answers. Shani is polite and put-together, but emotionally disconnected. She shows only perfunctory interest, because why should she be more forthcoming when her date will probably reject her anyway? These subconscious responses prevent Shani from being able to connect to her date, which leads him to  no. Of course, getting rejected again reinforces her belief that she’s unlovable. It’s a vicious cycle.

Harnessing Imagination

After identifying these subconscious patterns, Jackie encourages women to be curious, not judgmental. She acknowledges that this is easier said than done. “We want to be able to look at ourselves from that place of curiosity and compassion, because that’s what opens us up to see what we need to work on. Otherwise, we’re blocking ourselves because we judge ourselves so quickly.”

I comment that, generally speaking, as women, we’re excellent at being hard on ourselves. Jackie laughs and replies that that’s the yetzer hara rearing its head, and that learning to tune into our inner voice can give us the clarity to step out of self-judgment, and the space to actually work on our middos.

But how exactly do we tune into that inner voice? How do we access our higher wisdom? Jackie explains that a big part of connecting more deeply to ourselves requires quieting the rest of ourselves down.

I love this idea in theory but am at a loss as to how to practically do this. Jackie walks me through a brief example of an exercise she teaches her women (her course is over a nine-week period, so they get a fuller experience). She asked me to imagine that right when I wake up, before I start my day, I take six to ten minutes to check in with myself.

In a world that is so frenetic, the idea of taking just a few minutes to myself every morning sounds incredibly appealing, if a little unlikely that I’d be consistent.

Jackie describes it as a recalibration to get us back into the right place, in a methodical and practical way. She encourages me to take that time to think about what’s going on with myself physically, emotionally, and spiritually. Before I even leave my room, I run through this checklist, while sitting in one place, not walking around doing other things.

Physically: How is my body feeling? Am I groggy (probably)? Hungry? Emotionally: Do I feel energized? Am I stressed out? Excited? Worried? Spiritually: How’s my current relationship with Hashem? Do I feel close? Am I in a rut? Practicing acceptance from this place of observation allows for things to come back into balance rather than simply reacting when things happen. It engages the higher self, the part of us that has the bigger picture.

Making this a habit can provide tremendous clarity in the moments when we need it. Jackie has made recordings of these exercises, which her clients can listen to on their phone or computer with her voice guiding them into it. They don’t have to do it alone; she wants to be there to walk them through it.

Dimyon, the power of imagination, is another underutilized tool, says Jackie. Instead of jumping to the conclusion that after a so-so date, the guy will be saying no, and picturing the shadchan’s negative phone call, having the imaginary disappointing conversation, Jackie suggests picturing a pleasant conversation with the shadchan, getting a yes, and being able to look forward to another date.

It could feel like wishful thinking, or even setting yourself up for disappointment, but Jackie maintains that, “We use our imagination all the time for worst-case scenarios, but we don’t use it to envision a world that we want to live in, a world of abundance, a world of brachah, of shefa. If we don’t use our imagination for good, we’re wasting this power.”

All these tools are accessible, Torah-based, and open to anyone who puts in the work. And even though this is work, real work with no shortcuts, Jackie has seen incredible results in her courses.

Her smile broadens as she describes the transformations she’s seen. “As people connect to themselves more deeply, they open, they free up, and they receive from Hashem a lot more. They can also serve Hashem better, because they have that energy that comes with clarity. It’s life-changing work.”

She’s seen a phenomenon where about halfway through the course, girls who hadn’t been getting suggestions start getting them out of nowhere. They’re often shocked. “They shifted and were more open,” Jackie explains.

Putting It to Work

These gratifying results fuel her passion for sharing her work as she strives to achieve her goal to help women navigate the dating world with clarity, connection, and openness. And these skills are not limited to dating; her clients can tap into them after the chuppah, using what they’ve learned and internalized to build better, stronger marriages. “These tools come before whatever life situation you’re in, they’re applicable to everything.”

Jackie is quick to point out that when she experienced her success in shifting her own mindset, she’d had 20 years of practice doing internal work, plus the intense fundraising meeting to push her into some serious introspection. “It’s not a quick fix, it’s not magic, but this is the work, and this is what it looks like when you shift internally.”

It can take time to get used to tuning into our inner world, but as Jackie receives engagement announcements and wedding invitations from her clients, she’s even more invigorated to share these tools with more women.

“It’s work,” she says. “But it works.”

(Originally featured in Family First, Issue 816)