Converting to Orthodox Judaism Is a Lot. Here’s How 3 Women Did It.

The breakup had been painful, but Rivka was looking to get back on the dating circuit. But a matchmaker, of sorts, beckoned. And its merging of old-school and new-school technologies occupies a potent middle ground in a fast-changing Orthodox dating environment. On the new-school side of the equation stands Alan Avitan, a year-old businessman with a close-cropped beard and a ready smile who lives on the Upper West Side.

NEW YORK — “There’s no such thing as a bad date — there’s just a funny story,” says Jessica Schechter, a year-old modern Orthodox woman who teaches.

Their connection felt genuine and she was eager to cut out the middleman. Her future husband was less certain and suggested they wait. For instance, a shadchen acting as an intermediary at the beginning of a relationship served Lily in her early 20s, but was less effective as she matured. Lily attributes this disconnect to the reality that shidduch dating was originally intended for people in their late teens and early 20s.

He says that, thanks to his work, 58 couples have gotten engaged. He generally sets up young, secular Jews, because he feels that non-Orthodox Jews have limited dating resources. He also writes a monthly advice column in The CJN. Finding your soulmate is reuniting those two lost halves, whose destinies have been entwined from the start.

For Anna Sherman, a marriage and family therapist who for 17 years has made matches in her spare time, the motivation to set people up stems from a distinct sense of empathy for the emotional distress shidduch dating can cause. Three couples she introduced have gotten married. She often matches people who are baal teshuvah, or have become more observant, as she knows from experience that they are often stigmatized in the religious dating world. As a therapist, Sherman feels as though she has more insight into what matters to people and how they operate than many others do.

She cites what she says is a plausible scenario, wherein a shadchen might help a couple figure out if they should get married or break up. Is there any room to work on this, or are you at an impasse?