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

The topic at hand is irrelevant; it’s the vibe underneath that’s important


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…

Okay, he thought, time for food. “Do you like lokshen kugel?”, whereupon he was met with another “No.”

At this point he began to get nervous, and pulled out his last card, philosophy. “So,” he cleared his throat, “if you had a brother, would he like lokshen kugel?”

Generally, jokes are best left unanalyzed, but this particular one has some gems to be mined. First and foremost, kudos to the bochur for taking the time to prepare for the date. I know the word on the street is that it’s the boy’s “job” to keep conversation going, but I personally think that’s one of those silly rules we get hung up on.

Whoever is good at it should do it, and each partner should feel like they have equal responsibility to keep the flow going. Yes, it often works better when the boy leads the date in various ways, but it also works well when everyone does their part.

Second, this joke points to the purpose of small talk, which is to build connection. By bringing up topics that are universal to everyone, the initiator invites connection. Where he fell flat is in asking questions that provide one-word answers as an option. “How many brothers do you have?” can be answered in a single word. “Tell me about your family” can be as simple as, “I have two brothers and three sisters,” and as complex as, “We’re very close, kind of a traditional family, we get together every Shalosh Seudos at my Bubby’s house. Except of course, Tante Frumie, who moved to Zimbabwe a few years ago.”

See the difference?

Same goes for the kugel question. You either like kugel or you don’t. But if someone asks you what type of foods your family enjoys, that’s a gateway into a potentially rich conversation. And philosophy… well there’s no telling where that conversation could go.

So, for starters, before you go out, do your homework. Try to get a sense of what this person enjoys, and learn a little about it, kind of like preparing for an interview.

On the date, I highly recommend using open-ended questions if you’re going to ask questions at all. Better than questions are invitations to share: Tell me about your day. Tell me about your job. Tell me about your hobbies, what you like to do in your spare time. And then volley back graciously when you are invited to share.

People are different. I have a good friend about whom I always joke that she could make conversation with a doorknob. I, on the other hand, am not so interested in details, but I’m fascinated by how people feel about the details.

Imagine a friend just got back from a week in Hawaii, and you all get together to hear about the trip. Some will want to hear about every volcano and every type of pineapple. Others will be much more interested in how different the culture is, how she acclimated, and if the group she went with was in sync with each other.

You have to read the room and tune in to the metamessages. And that’s your point of connection.

When you figure out what makes the other person tick, you’ll realize the topic at hand is irrelevant; it’s the vibe underneath that’s important. My advice to you is to combine all these pieces of insight for a winning first date combination: Do your homework, employ the “share” method once you’re on the date, and tune into your date’s style to match frequencies.

I hope this helps!

All the best,



Sara Eisemann, LMSW, ACSW, is a licensed social worker and a dating mentor. She lectures on topics related to relationships, personal development, authenticity, and growth. She welcomes questions, comments, feedback, and interaction at matchquest@mishpacha.com.


(Originally featured in Family First, Issue 815)

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