One of the saddest experiences I’ve had dating was Stricken. I noticed him at a party. It was hard to miss him beneath the colored streamers. He was stick-thin and wearing a wig. His glasses seemed to fill out his shrunken face. I wondered what the matter was. People seemed to know him from school, and he joined in the conversations easily. He ambled over and started making small talk. After a few moments, he had put me at ease, and I could put aside what he looked like. Then the unexpected happened.

“Would you like to go out?” he asked. Zoom. Suddenly his skeletal appearance and his wig boomeranged right back into view. No one had ever met me at a party and asked me out on the spot. I was flattered but caught unawares. I couldn’t think straight and said, “Yes.”

I could not sleep that night. As I tossed and turned and fought with my blanket, I had more time to think. Was I a shallow person who did not want to be seen in public with Stricken? Would I be thrilled to date him if he were not sick? Would Stricken give me a chance or be remotely interested in me if he were not ill and other girls did not turn him down? Would he be fairer to me than other men had been? The men who judged me by where I lived, what school I had attended, my parents’ lack of degrees and professional credentials, or the fact that I was first-generation American?

I did not know, but I re-evaluated. He was clearly smart, confident and probably incredibly cute when he wasn’t ill. G‑d was giving me a chance. In this cut-throat dating scene, G‑d had sent a man who had me at the top of his list. This was an opportunity. I would look forward to this date.

Stricken picked me up and started driving. I was glad we were both facing the road because he had seemed shockingly weak and gaunt at the door. He had looked at me with hunger in his eyes—the look a man has when he sees a beautiful woman out of his reach. I was not accustomed to being looked at that way. It frightened me.

At the restaurant, he again tried to put me at ease. But this was different from the party where everyone knew him. We were in a public restaurant, where every waiter suddenly appeared incredibly hale, hearty and handsome in comparison, where the couples at the other tables turned to stare, and where I was clearly struggling against the shallowness in my mind. Perhaps I was not mature enough to handle this. He was created in the image of G‑d, and he was a good, good person. Why G‑d had afflicted him with this illness was hard to understand. It weighed on me. We hadn’t addressed it at all.

“Um … there’s something I … ”

“It’s OK,” he knew where I was going with this. “It’s cancer, but I am a fighter and plan on beating this thing.” He slapped the table as though it were the “thing.”

He told me about the rabbi he had gone to for a blessing, who had gifted him a silver Kiddush cup with a blessing for a long and healthy life.

He looked at me, “I’m determined to get married and use this Kiddush cup at my chuppah.”

Oh my, oh my, oh my. My heart raced. Had he set his heart on marrying me? I studied the stain on the tablecloth. I could not meet his eyes. I wanted to go home and cry.

Later at home, I cried to my mother about illness and choices, and what-do-I-dos. I prayed to G‑d, “Please help me navigate this. Tell me what to do.” I could barely last through that one dining experience, how could I date or marry him? What if he died, G‑d forbid? I’d be a young widow. I was a mess after one date; what would happen if I continued to date him?

If I rejected him, would it hurt him after one date as much as Mr. Handsome’s semi-rejection after several months had hurt me? Yes, I thought, it would. Should I continue to see him because I felt too sorry to reject him? He would not want that. This was going to be painful one way or another. I couldn’t handle it.

I was a complete and utter wreck.

He called and chatted about his plans for our next date. My stomach was lurching. I had to stop this right away. I did not want to give him false hope for another moment. I interrupted him. “There’s something I need to speak to you about.” He was quiet. He knew what was coming. I felt dreadful.

“Don’t bother,” he spat back. “You think I don’t know what you’re gonna tell me? You think I haven’t heard it before?” His tone shocked me. He had been so amiable and solicitous until now. I had expected hurt, shock or sadness, but not this poisonous anger.

“People who look like you don’t have to worry about getting married like I do.” People who look like me? Some men considered me attractive while others did not, but Stricken implied more—that I was exceedingly attractive and had never experienced rejection. That was entirely untrue.

I tried to understand his frustration and anguish. I wasn’t burdened with ill health and my own mortality as he was. He hung up on me. I stared at the receiver in my shaking hand, then placed it on the table. I couldn’t fault him for what he had done, but I still could not hang it up. Then I laid down flat on my back, my eyes open but unseeing.

I willed my tears not to dribble down my cheeks. I tried to steady my breathing. We are all quick to rationalize our own actions and judge others, but we should do the reverse. As difficult as my situation was, his was life-threatening. I would give him the benefit of the doubt. We are taught “Do not judge your fellow, until you have stood in his place.”1 I would try to understand his suffering, the way I wished others understood mine, which seemed petty now compared to his. I would count my blessings.

Weeks later, I tried to call him, but he refused to speak with me. Did he not understand that I didn’t want to hurt him, but that I didn’t want to mislead him either? That one could not force things? “Let the honor of your fellow be as precious to you as your own.”2 We never want to hurt, anger or shame anyone. We are taught to visit the ill and gladden them in their illness. We are taught to be honest. And yet, by being honest, I had wounded him deeply. I had angered him. “Ethics of Our Fathers” tell us: “Do not try to placate your fellow in his hour of anger.”3 So I would give his anger the space it needed.

Months later, I was home alone when someone messaged that Stricken had passed away. I stared at the words on my screen in disbelief. To find out something of this magnitude in such a casual manner had taken me aback. I had not believed he would die. Should I have continued seeing him to gladden his last few months on earth? I had not personally known anyone as young as Stricken who had died. This time, I could not control the flood of tears. They flowed and flowed. I jumped into the shower trying to wash away my self-loathing, my unforgiven sin, my anger at him, my pain for him, my regrets.

I learned that it is painful to be rejected, but sometimes, it’s equally painful to turn down someone else. I realized that despite the hardships of my dating challenges, I still had the beauty of life, and that it was precious, no matter what the challenge. “Who is wealthy? One who is content with his lot.”4

The relentless storm of tears went on and on. I thought of his silver Kiddush cup cradled in its velvet box, unused. My tears would have overflowed that cup.