Dating for Success: How I Stopped Dating for My Parents – And Started Dating for Me!

My parents emigrated to Toronto after the war and had four children who they treasured – 3 boys and myself, the youngest child and only girl in the family.

My proud European, heimish parents were very traditional and had strong beliefs about how we should conduct ourselves, from how much value to place on education and how to dress to what type of person we should marry.

I was always very much under the influence of my parents, who I loved and revered. Both of my parents spoke many languages. They were well educated, sophisticated people who were respected in the community. My father was a brilliant Talmid Chacham who worked for the government and learned every moment he could. My mother, in addition to keeping a beautiful home, was a charismatic school principal adored by all who knew her.

When I turned 19, I turned to my parents for guidance in shidduchim and they made their expectations clear. I was to find a smart, handsome boy from a fine heimish family similar to ours, who was a college-educated professional and also a top-notch learner and Talmid Chacham.

“Only the best for Faygie,” they would say, truly wanting the best for me.

I was a well-liked, pretty girl who excelled in school and earned top grades. I always strived to attain perfection to make my parents proud. When it came to shidduchim, I knew they wanted the very best for me and I trusted them implicitly. After all, they had helped my brothers find their wives. Their wives are wonderful women who tick every box.

With the long tough list of criteria my parents laid out, it wasn’t surprising that finding suitable boys to date was not a walk in the park. I dated extremely infrequently – maybe once or twice a year if I was lucky.

When my parents did agree to a suggestion, after weeks or months of careful research, I felt tremendous pressure. Before each date, my mom would give me a onceover and fix any hair out of place.

I was expected to give my parents a play-by-play of how the date went. With the very best of intentions, they would analyze our conversations, in particular what I said or didn’t say, and coach me on how to approach the next date.

In retrospect, it’s not surprising that most of the boys I went out with rejected me. Because of parental pressure, I was so uncomfortable and in my head on each date that we both were left feeling little connection.

And though I was extremely well put together and dressed beautifully, I wasn’t attracting the boys I dated because I was too closed-off and intellectual rather than vulnerable and emotionally open.

The truth is, the boys did not feel a connection because I was not letting them get to know me. It wasn’t until I was older that I realized they couldn’t get to know me because I didn’t have my own sense of identity. I was dating for my parents and it wasn’t working for me.

After earning several university degrees, I followed in my father’s footsteps and got a great job working for the government. I excelled at work just as I had in school and had a wonderful group of friends, but through my twenties, my dating life continued on the same unsuccessful path.

The older I got, the narrower my dating pool became. My dates were few and far between. Though I tried to stay positive and pump myself up before a date, it was hard to squash my nerves. I came home feeling drained and discouraged.

As I approached 30, I felt a deep lack in my life. More than anything, I wanted to get married and start a family of my own. I recognized that if I wanted to find my bashert, I needed to make a change in life by becoming more emotionally independent and creating some distance from my parents.

When a government job opportunity came up in Montreal, I grabbed it. Moving to a new city gave me the courage to take another important step – setting clear boundaries with my parents.

Every time they called, and they called often, they inquired about my advancements in dating.

“Ma, tatty, I’m not discussing my dating life with you anymore,” I replied one day over the phone, with as much strength as I could muster. It caused tension between us, but I knew I had to cut them out of my shidduchim completely so I could start thinking for myself.

Moving to Montreal, my real journey in dating began. After years of going out maybe once a year, I started dating more frequently. I adjusted my parent’s rigid criteria, and started dating different types of men.

Not long after my 32nd birthday, I dated a man six times and I really liked him, but he ended it suddenly and unexpectedly. Although he liked me, he apparently didn’t feel the deep connection he needed to move forward. It was a crushing blow.

Not long after that I dated another man for several months. He was 39 and fit all my criteria on paper. But it soon became clear he was a commitment-phobe, and we broke it off. Another painful blow.

Over the next few years, I continued actively putting myself out there and expanding my dating pool to include men who didn’t come from heimish backgrounds, men who weren’t professionals, older men and divorcees. Being more open-minded to different men definitely meant I dated more frequently, but I still didn’t feel the connection I was searching for.

After years of struggling to find my bashert, when I was in my mid-30s, I reached out to a Rabbi in my community known for helping singles by empowering them to figure out why they’re struggling.

After many (many!) conversations, he helped me understand how I came across on my dates. Though I no longer reported to my parents, I still took a very intellectual approach to dating. Rather than letting my guard down and being myself, I came across more like a professor, speaking about politics, interests and philosophical ideas.

While the men I was dating found me attractive, appreciated me as a conversationalist and respected my intelligence, they weren’t getting to see my softer side, my silliness or my emotional vulnerability.

Reflecting on how I approached dating and carried myself, it began to make sense why men said I was a great girl, but the “connection” just wasn’t there.

Finally, I understood that to meet my bashert, I had to develop a soul connection – and that could only happen if I was vulnerable.

With this insight, I continued dating. I further expanded my dating criteria, dating shorter guys, overweight guys, even a man who was deaf. Anyone who said yes to me and who was emotionally healthy was worth a cup of coffee.

When I was 38, a certain name came up a number of times – Mordechai. Mordechai was 47 years old, had been widowed about a year earlier with five children.

A friend of mine was Mordechai’s second cousin, and she raved about him. “He’s a wonderful devoted father, a Talmud Chacham, smart and independent – he’s a gem.”

He sounded terrific, but I wasn’t sure how I felt about marrying a man with such an established family of his own.

Over the next month or so, I had a few awful dates.

So when my friend called again to suggest “Mordechai – the gem!”, I figured “Why not?”

When I met Mordechai, I instantly felt at ease with him. Our conversation flowed easily.

A few dates in, Mordechai shared what he liked about me – my spirit and my spunk! He said he loved my laugh and appreciated my easy-going nature. I couldn’t believe it. He didn’t comment on my IQ, my vocabulary or the fact that I read the Wall Street Journal – he really saw ME – the real me – on a deeper level.

After a few months of dating, Mordechai asked me to meet his children. Surprisingly, though I had been nervous, it went extremely well.

The following week, he asked to meet my parents! I’ll admit, I had palpitations! My parents had never been easy people to impress.

Incredibly, my parents who had always wanted the very best for me and were critical of my shidduch prospects had nothing but words of praise for Mordechai. They knew he was a wonderful man who would be a greater partner just as he was a devoted father.

We got engaged and the rest is history. We just celebrated our 5th wedding anniversary.

Here are the lessons:

When it’s Time, It Will Come

I dated for almost two decades, so I understand the pain older singles face wondering when their turn will come. My experience taught me that when Hashem decides it’s time for your bashert to arrive, it will come.

Sometimes older singles have to achieve their own personal growth, and others simply have to wait for their zivug to be ready. For some, their bashert isn’t even frum yet, for others he or she may currently be married to someone else or have to heal from a personal trauma to be truly marriage-ready.

Don’t Date For Your Parents

I spent many years under the influence of my parents in shidduchim and it was suffocating. Though I know they wanted the best for me, their impossible Mr. Right criteria and constant scrutiny negatively impacted me. The pressure I felt from them made it challenging for me to relax and be myself on dates. Whether you have parents who are impossible to please or who offer “constructive criticism” after requesting a play-by-play of your dates, it may be time to set some boundaries.

When I set firm boundaries with my parents, I was able to decide for myself what my true non negotiables were in a partner and broaden my dating pool. Instead of feeling nervous on dates, questioning whether I was saying or doing the right thing, I was able to let go and be myself.