A young man and woman face each other across a table in a hotel lobby or other indoor venue, looking nervous and awkward. You don’t need ruach hakodesh to realize they are on a shidduch date.
You can tell by the fact they are both neatly groomed, wearing freshly pressed clothes—stylish, but not overdone. Their shoes are shiny. They both sit up straight, no slouching. They scan the room, stare into their Cokes, occasionally make eye contact and then look away.
Their conversation is filled with strained silence and forced small talk. They sip at their drinks self-consciously. Finally, the guy clears his throat in an attempt to start a conversation:
Moishy: Er… so how’s your Coke?
Shaindy: Good, thanks. And yours?
Moishy: Yeah, really good.
More agonizing silence follows. You can almost read their minds. Moishy thinks, “Come on, say something already! This is torture.” Shaindy thinks, “Why doesn’t he ask me any questions? Or maybe I should—but I don’t know what to say! How can I get out of this?”
On it goes with more awkward moments, more routine questions, and staring into their Cokes, as if the answers might be hidden beneath its bubbly dark surface.
As would-be shidduch dates go, this plane may be slow to leave the gate and get onto the runway. Will it pick up speed, gain altitude, and soar skyward . . . or will it just sit there on the tarmac, not going anywhere?
Don’t let this happen to you! It’s true that first shidduch dates can be one of the most nerve-wracking, anxiety-producing situations in our society. Sometimes they may lead to the chuppah and building a bayis ne’eman b’Yisrael. Sometimes they don’t go anywhere at all. The situation can be helped along with some well-chosen shidduch date questions. Let’s review a few general guidelines:
Listen as much or more than you talk. Some people consider themselves skilled communicators because they can talk endlessly. But the ability to speak is only one part of the equation—and not the most important part. The best communication occurs with an even and equal exchange between two people. Think of conversation as a tennis match in which the players lob the ball back and forth. Each person gets a turn—and no one keeps the ball.
Peel the onion slowly. Getting to know someone new is like peeling an onion one thin layer at the time. It’s a slow and safe process. But some people, overeager to get into deep and meaningful conversation, go too far too fast. They ask personal or sensitive questions that put the other person on the defensive. Should the relationship evolve, there’ll be plenty of time to get into deep topics. But at the beginning, take it slowly.
Don’t vent. If feeling inhibited is a problem for some people, others go to the opposite extreme: they use a shidduch date as an opportunity to vent. When a person reveals too much too soon, it can give a false sense of confidence. Premature or exaggerated revelations are due to boundary issues, unresolved pain, or self-centeredness.
Genuine interest goes a long way. Maybe your first date questions will lead you to discover that this person is your beshert—or maybe not. Great communication starts with being genuinely interested in the individual you’re with and paying close attention to what he/she says. The process begins by providing lots of space for the full expression of information and asking follow-up questions to further draw out the person talking.
With those thoughts in mind, let’s think about specific first shidduch date questions.
Try these:
1.Who has been the biggest influence in your life?
2. What kinds of things make you laugh?
3. What’s your favorite place in the entire world?
4. Who is your best friend? What do you like about him/her?
5. What was your favorite book of all time? Why?
6. What is your favorite way to spend Shabbos?
7. Do you have any pet peeves?
8. What was your family like when you were growing up?
9. What were you like as a kid?
10. Did you—or do you—have a nickname? What’s the story behind it?
11. Who was your favorite teacher? Why?
12. What do you dislike most about the shidduch dating process? (Tell me so I can avoid it!)
If necessary, print out this list and take it with you!
Wishing you much hatzlacha!
