After 18 Months Without a Match, She Took the First Step

A 39-year-old single woman wrote about a long stretch of frustration, saying she had gone 18 months with zero relevant introductions and felt as if the dating market had left her behind. She described feeling trapped by routine, family obligations, and repeated disappointments, and said that at 39 the statistics no longer seemed to be on her side.

Her turning point came at the Jerusalem Book Fair in Safra Square, where she was browsing the new book by the late Rabbi Jonathan Sacks. Beside her stood a man she estimated to be about 45, someone who appeared intelligent and thoughtful. At first she froze, wondering whether to approach him at all, and feared public embarrassment if he rejected her.

She eventually decided to act. Carrying no plan, no intermediary and no “filters,” she went up to him, asked him about the book he was holding, and smiled. “I was sure I would get the big no,” she wrote, but instead he smiled back warmly and engaged her in conversation. They spoke about Sacks, Jerusalem, and life after 50, and the exchange felt easy and natural.

The conversation led to a date later that evening among the book stalls. The writer shared her story as an example of what Sacks described as covenant, an act of choosing and doing rather than waiting for life to happen. Her message was that people should stop counting years and disappointments, and start counting attempts, because one brave step can change the script.