25 unconventional icebreakers every Jew should know


“Try before you buy.” This is a smart tactic not just for investing in stuff but when considering a new relationship, romantic or platonic.

When you meet someone for the first time, how do you dig deeper to break the ice and find out more personal information that may help you decide whether you want to get to know them better? At the same time, most of us want to avoid initially being too intrusive. We’re reporters by training and sometimes are accused of asking too many questions.

An article titled, “Cold Open: Break the Ice by Looking Inside Someone’s Fridge: How your leftovers can spark a meaningful conversation” (March 01, 2022) by Kevin Cool in the “Stanford Graduate School of Business Journal” (Insights section) offers one solution. We picked up on this concept as a way to peek into someone’s life (or fridge) beyond the superficial.

Most of us are familiar with the polite, trivial banter we use to get to know someone. Before Margaret virtually tutors a new student, she always spends about 10 minutes asking: What is your favorite color? Favorite snack? Favorite thing to do on a weekend? Favorite book or movie? Tutoring on a screen hardly offers access to a student’s fridge but does allow a peek into their room or home, albeit it’s often a tiny corner where they have their device set up.

Even at 8 years old, Barbara’s oldest grandchild likes to pose his “question game” at the dinner table when family gathers. Often, it relates to his current interests. “What’s the superpower you wish you had?” he’ll often ask initially. “Where do you want to travel that you’ve never been?” might follow. And he knows how to keep the conversation going—or toss the ball as he says to another person, by giving each person a turn to ask their questions. The results have been far ranging and illuminating.

Similarly, when we meet someone new and try to strike up a conversation, we often start with the usual go-to’s, some of which we don’t like but are expected. The first round might be: Are you married? Have kids? Grandkids? Where did you go to school (college rather than high school even in St. Louis)?

But we like to veer off path and focus on a person’s interests: Where they might work, what they like to do in their spare time, what is in their refrigerator, in their purse. and so on.

Then, we may take this line of inquiry a few steps deeper through a series of offbeat questions. You’ve heard the “What’s in your wallet?” in TV ads. If you ask this and they answer, they may not be telling the truth or it’s a sign that they brag too much.

But we like to go for broke. The following 25 questions are more than icebreakers; they can be deal breakers in this clever game of meet and greet. If you feel these cross a boundary, delete from your list. Pleading the fifth is allowed but it might be a red flag. Here are some examples of really breaking through:

  1. What has been your most embarrassing moment? (Keep it clean.)
  2. What’s your highest achievement? (Let’s hope they don’t answer by saying getting to work on time or climbing a mountain, but we would be impressed by Mount Everest.)
  3. Do you have to count sheep to fall asleep? What is the average count? (Could be a sign they have insomnia and could be crabby to be around.)
  4. What is in your desk drawer if you use a desk? (If it’s a gun, run fast and cross them off your list.)
  5. What is your best talent? (Hopefully, it’s not karaoke or blowing smoke rings with their vaping pen.)
  6. What is the most exotic food you enjoy? (Eyes, insects and other strange body parts are off our list but on many others’, we’ve heard and read.)
  7. If you could change one body part, what would it be, and why? (TMI-too much info–might be off-putting and if it’s the usual neck, eyes, nose we could ask another question of why?)
  8. Do you have a pet? What might that pet say about you? (If it isn’t complimentary, move on)
  9. If you made a movie, which actor would play you? (If the shoe doesn’t fit, smile and accept they have an inflated image of themselves.)
  10. If you could invite three people to a small dinner party, who would they be and why and what would you serve? (Gives you a clue about the company they’d love to be with and their dream meal.)
  11. What is one way you tend to waste time? (If it’s matching socks or polishing silver, you know they aren’t the ambitious type.)
  12. Is there something you’ve dreamed about doing but haven’t yet? If so, why not? (This will measure their risk-taking meter which might have been simply leaving the house during Covid to parasail or audition for Wheel of Fortune.)
  13. What’s usually in your grocery cart? (It’s a clue to their dietary preferences and maybe an explanation of why they have a big gut. If it’s a lot of food, it can be telling about their family composition. Follow-up questions can be key to good details.)
  14. What is the composition of your gut bacteria? (Let’s not get too graphic but a clue to good or bad health. Many won’t know and may rush to find out.)
  15. Do you believe in tattoos and how many? (If you spot on their arm a tattoo of Mitch McConnell, no reason to have a panic attack. But now you know something about them politically.)
  16. How much time do you spend on the phone with tech help or customer service reps each week? (If a major daily activity and time suck, you know the person is low-tech and could use some good recommendations on how to start mastering the skills.)
  17. How many toilet paper rolls or towels a week do you buy and use? (A clue about bathroom habits or how many visitors or family members living with them they have.)
  18. How many doctor’s appointments do you have a month? (If more than six, forget it. Do you want to hear about all their health issues? We don’t unless they become a good friend.)
  19. What pet peeves most annoy you? (This could be an immediate deal killer if they cite a few you regularly do such as typing on the computer while talking or always taking the better offer from a friend or family member.)
  20. What ingredients do you use to make cookies or cakes? (If they use cheap store brand butter and chocolate chips, you might be food opposites. If they buy the more expensive brands, they might be our kind of folks.)
  21. What’s on your device’s music list? (If it’s country or heavy metal and you’re a pop or classical music fan, tune them out fast.)
  22. Do you have a favorite TV series? (If something extremely bloody and violent, who knows, the person you’ve just met might not be a good TV buddy unless they say they’re flexible about watching what you like.)
  23. What is your biggest fear? (Public bathrooms, bugs, other vermin, airplane flights, lightning storms or your mother-in-law are understandable.)
  24. What is your favorite room in your home or apartment? (Tells a lot whichever room they designate.)
  25. If you could be good friends with anybody who’s alive in the world, who would it be and why? (This says a lot about their values.)

Taking this approach is a personal choice and not for all. The bottom line is that there are many fish in the sea, and we’ll probably hook new people we meet in the future with some of these questions. We’ll also learn which don’t appeal and we should drop fast.