Finding their beshert later in life

True love can be found at any chapter in our lives. Below are two incredible stories of couples in the Jewish community who found their beshert, their soulmate, later in life.

Gail Regenbogen & Howard Swibel

If you’re looking for a love at first sight story, this isn’t it.

This is a romance that began with an awkward first date and grew into a partnership built on a foundation of shared values, passions, and mutual respect.

When Gail Regenbogen and Howard Swibel met, they had each recently undergone the major life change of transitioning from being married to being single. Gail’s husband passed away unexpectedly, and Howard and his wife divorced. Each had been married to their partners for more than 30 years, and found the task of finding love again daunting. But they knew love was out there and were willing to do the work to find it.

Howard went on more than 80 dates and worked with three matchmakers to find his other half. “One matchmaker came to me with a clipboard and asked me what I’m looking for in a mate. I said, ‘I’m not buying a house; I can’t give you a list!’ I said, ‘according to our sages, the most important characteristic is kindness, so I am looking for a kind woman.'”

When a mutual acquaintance connected the couple in 2016, Howard said he found a partner who is not only kind, but chooses life every day.

Gail and Howard share a passion for travel, politics, tzedakah, and learning. A few years ago, Howard took Gail on her first trip to Israel. Now, they lead missions together and are active members of the Anti-Defamation League.

Their children and grandchildren are thrilled that the couple found each other.

Gail and Howard married during the COVID-19 pandemic at their condo in Skokie, streaming the ceremony over Zoom so that their entire family could participate.

“I always tell people, falling in love again is like when you have your first child,” says Gail. “You can never imagine loving a second child as much as you love the first, and then you realize that your heart is big enough.”

Bob Silverstein & Cheri Friedman

Listening to Bob Silverstein and Cheri Friedman tell their love story can only be compared to the opening scenes of When Harry Met Sally– not only because they finish each other’s sentences, but because of the uncanny ways their lives overlapped before becoming a couple.

They technically met at Niles West High School, but were in different grades, so they didn’t cross paths much. However, Bob was good friends with Cheri’s cousin, Alan. Cheri’s family was incredibly close, so when Bob wanted to ask her on a date, he asked for Alan’s permission. Alan said no, so Bob asked out a classmate named Marsha.

Bob and Marsha dated through college and got married after graduation. By this point, Cheri was also married and teaching at a local elementary school. Coincidentally, Marsha taught at the very same school, and the two became friends.

Over the years, Bob, Cheri, and their respective families also encountered each other at bar mitzvahs, weddings, and charity events.

When she was in her 40s, Cheri and her husband of 20 years divorced. Several years later, Bob lost Marsha to cancer. Despite these painful losses, Bob and Cheri believed in the possibility of finding love again. Little did they realize that they each already knew their beshert.

A mutual friend reconnected Bob and Cheri five years ago, and the romantic connection was intense and immediate. Within a few dates, they were already travelling together. The couple was staying at Bob’s house in Florida when COVID-19 hit. They quarantined together and loved every second of it–and continue to spend every possible moment together.

“It took me 35 years to find him, you think I’m going to leave him now?!” exclaims Cheri.

Bob and Cheri married in 2021, surrounded by their overjoyed families. “I’ve never seen my ‘Ga-Ga’ so happy before,” Cheri’s grandson wrote in a letter to Bob.

“We are so lucky,” says Bob. “This is the kind of love they write stories about.”

Jenna Cohen is a development professional and freelance writer living in Chicago.