Recently, we marked the 15th day of the month of Av, a day that has such special meaning for me. Each year, as we come to this date on the Jewish calendar, I think back to the 15 days that changed my entire life, how I almost threw it all away, and the incredible lessons I learned during that crazy fortnight plus one.

To understand this story, you have to know that everything I do in my life, I do with the philosophy of “go big or go home!” When I met my hubby, we dated, broke up, got back together, and even got engaged, all within 15 days. We got married less than two months later.

When we first met, things clicked immediately, but then, typical me, I got cold feet. I’m talking full-on hyperventilating in a bag while frantically making a list of everything I was nervous, scared, and concerned about in the relationship. What I didn’t do was make a list of everything that was so right about this young, beautiful relationship that was blossoming before my eyes.

It’s often our human tendency – and I am guilty of this – when we’re faced with something that seems too good to be true, to look for the catch, to take a step back and obsess over all the reasons why it’s not perfect.

Instead of just going with it and trusting our hearts, many of us find a litany of reasons why the relationship won’t work. We convince ourselves that it’s not what we’re looking for. That’s what I did. I almost threw away my entire future because I was scared witless.

I made my ridiculous list of all the things that were “wrong,” and then, brace yourself, I broke up with him by leaving a message on his answering machine. I was crying and sobbing and told him that even though everything seemed terrific, I was sorry because this just wasn’t going to work out.

Yet here’s where the story gets good. Being the incredibly clear and confident human that he is, he called me back and said, “There is no way you’re breaking up with me.” He then announced that he would pick me up for our date at 6, and he did. What a guy.

I brought a package of tissues and cab fare with me because I was convinced we would break up, just in person this time. But after our date, we went to my rebbetzin’s (rabbi’s wife/female religious teacher) house. Rebbetzin Judy Young, may her soul rest in peace, took one look at us and told me flat out: “He is the one.”

Having a good mentor

My rebbetzin was a mentor and guide to so many young American Jewish women at the time, and she was able to give me that voice of confirmation I desperately needed. She helped me work through my fears and showed me that they were not even a molehill, and yet I was making a mountain out of them.

She showed me that I had fallen into the classic trap of self-sabotage that so many women do. At this point, I had been dating for years and had dated over 50 guys. Yes, you read that right. How could I possibly fathom that this would be the one for me?

I needed a coach, friend, and adviser – someone who was strong and wise, whom I trusted completely and knew only wanted the best for me – to voice their opinion and calm my ridiculous fears. For me, it was my rebbetzin. After meeting with us and interviewing my husband – yes, she grilled him like she was hiring a CEO for a Fortune 500 company about to go public – she turned to me and asked, “So, when’s the wedding?”

She helped me see that we have the same goals in life, the same dreams and passions, and that we both wanted the same things for our future and our future family. She was right.

It’s been 21 years of sheer bliss. Not because it has been absolute perfection but because it has been two decades of hard work as partners dedicated to building the life we set out to build. Over that time, we’ve been blessed with six precious children, thank God, and now my oldest daughter is dating.

She knows this story because my hubby broadcasts it like breaking news, while I pray for selective amnesia. But she, and anyone who’s survived our Shabbat table, has learned my hard-won lesson: Get good advice from people you trust, then actually take it.

The hardest part of dating is feeling like you’re navigating this scary world alone. No one should ever do something as monumentally important as choosing whom to spend the rest of their life with all by themselves!

It is so critical to have a sounding board, someone you trust to work through the fears and concerns with, and to remind you to not only create that dreaded list of worries but to create a list of all the good things that click and help you reflect on those beautiful connections.

Building the Jewish future

Earlier this month, I had the incredible honor of hosting what turned out to be the world’s largest Jewish online speed dating event, ever! This massive, revolutionary program was put together by Partners In Torah, DateNight AI, Coronacrush, and Aish, along with 30 other partnering organizations. The event had 6,747 Jewish singles participate and go on more than 15,700 dates.

It was remarkable and so moving to be a part of. I was able to share some of this hard-won advice with the participants at the beginning of the event. But it was also a poignant moment in Jewish history for me to take on this role as host because it felt powerful and victorious. As the Jewish people have been in a constant state of war on multiple fronts for the last 22 months, this moment felt like a vindication of sorts.

It felt like the victory over the hate we have seen around the world aimed at Jews and the Jewish state every single day since this war began on October 7, 2023. There is so much power when Jewish singles choose to come together and voice their desire to continue building Jewish families based on shared values and love.

Each Jewish person is a light with their own unique spark, and when that spark joins with another to create another Jewish family, it brings a light into the world that simply cannot be extinguished. Jewish families are our story of survival.

This incredible event proved to me that if we are willing to take that leap of faith, get over our overly negative and exaggerated lists of fears, concerns, and worries, and make the effort to connect with one another on a deep and engaging level, then each of us can open our hearts to connect with another and literally change the world.

Just as my beloved rebbetzin did for me all those years ago, it is now my turn to do this for others, both for my precious daughter and for the thousands of Jews around the world who are searching for their soulmate.

Please God, may we be victorious, and may all the singles who are searching find their soulmates soon and build beautiful Jewish families together.

The writer is chief communications officer and global spokesperson for Aish, following a distinguished career as an award-winning producer and marketing executive with HBO, CNN, and Food Network. She is also an eight-time bestselling author.