“I’m Bad at Dating Because I Can’t Make Small Talk”

Dating is a nightmare for me. Don’t get me wrong — I love meeting new people. I have a lot to share, and I’m curious about people and new ideas. The problem is that I can’t make small talk for the life of me. I already know what the weather is, and I’m not interested in traffic patterns. So first and second dates are really hard for me.

I get predictable feedback that I seemed nervous or that I’m cold. I’m neither, I just find small talk excruciating, and I’m terrible at it. Also, “people say” it’s the boy’s job to keep the conversation going, so I’m wondering if this is even my problem.

What do you suggest?

Sick of Small Talk

Dear Sick of Small Talk,

Well, now you’ve given me no choice but to tell my all-time favorite dating joke, with apologies in advance to those who’ve heard me tell it more than once.

A young chassidish bochur was about to have his beshow, and was exceedingly nervous that he would have nothing to discuss with the fine young woman he was about to meet. He turned to his mentor for guidance, and the older man told him, “You can always talk about the three F’s: Family, Food, and Filosophy.

Emboldened by this information, the young man went confidently to his date — and was met with awkward silence. He ran through the formula in his mind — family, food, philosophy… and began his foray into dating conversation.

“So,” he queried the young woman, “do you have any brothers?” and was met with a flat, “No.” Hmm…