Yankie and Rochie were in a car together, and were attempting to make conversation. “Attempting” is the appropriate way to describe it, because conversation between them was difficult and awkward. This made for an uncomfortable car ride.

Further complicating matters was the fact that Yankie and Rochie were expected to converse with one another despite being complete strangers; in fact, they really had no other reason to be there. Despite being coached on what to talk about and how to express themselves, and despite having gone through many similar experiences with other people, there were many gaps and dead-ends in the conversation, which only further heightened the discomfort.

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Needless to say, neither Yankie nor Rochie enjoyed the experience, despite the way they smiled and pretended otherwise. It was clear that they had little chemistry, and whatever they were told they had in common was surely exaggerated. Maybe they would be persuaded to give each other “another chance,” though they would look forward to it with dread or indifference at best; maybe they would go through this unpleasant experience all over again with hopes of developing a rapport; maybe they would eventually become comfortable in each other’s company; maybe they would become capable of talking naturally to one another as they could with everyone else; maybe they would even wish to get married.

But probably not.

Yaakov and Rachel also had their first conversation during a car ride. However, the circumstances surrounding this meeting were entirely different. They had each spent Shabbos in the same neighborhood and were sharing a ride back home. They had never previously met, and knew nothing about one another, yet they conversed freely and without strain. When there was a lull in the conversation there was no palpable tension in the air. They were both comfortable presenting themselves without subterfuge and acting naturally, since there was no pressure and no expectations. After all, they were just two strangers sharing a ride.

When they parted at the end of the ride they still hardly knew one another. After this one chance meeting they definitely had more questions about one another than answers – but that’s always the case. They discovered that they had a lot in common. They also discovered that they were not entirely alike in terms of background, personality, and even religious outlook. But after this lengthy, engaging, enjoyable conversation, these differences seemed trivial to both of them. In fact, rather than cause tension and anxiety, these differences actually contributed to the conversation.

Yaakov and Rachel found each other to be interesting, similar enough to understand each other yet different enough that their time together was never dull and monotonous. They even discovered qualities in one another that they had never before thought of in a potential date, yet appreciated now that they had stumbled on these qualities. Not only that, they discovered that some of the trivial, tangential “requirements” they fussed over when being set up just didn’t matter. This real person was so much more than a generic list of qualifications. Needless to say, they made it their business to meet again, and they both looked forward to it.

After two weeks of nerve-wracking negotiations and deliberations, Yankie and Rochie agreed to meet a second time as well. They went out for dinner at one of the usual restaurants. They found a few things to talk about, but again it petered out before too long, and they found themselves grasping to fill the empty spaces. They didn’t really care how many siblings the other one had and what they all did, but they feigned polite interest as they exchanged monologues. Rochie kept glancing around the room, hoping no one she knew would see her. Yankie almost gritted his teeth when he saw the bill, and reminded himself that this was hishtadlus. They were also not very attracted to one another, and did not find that spending more time together helped matters.

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Rabbi Chananya Weissman is the founder of EndTheMadness and the author of seven books, including "Tovim Ha-Shenayim: A Study of the Role and Nature of Man and Woman." Many of his writings are available at www.chananyaweissman.com. He is also the director and producer of a documentary on the shidduch world, "Single Jewish Male." He can be contacted at [email protected].