A card deck of 200 questions to jumpstart meaningful and interesting conversations – to laugh, to share, to get to know each other, and to build your potential relationship.

These can help you uncover deeper and richer insights about yourself and your date and your potential relationship. 



The questions get progressively deeper and more personal and are designed to be used at different stages of the dating process.   Don’t bring the whole deck with you; bring jsut the ones applicable to the stage you are in currently.

YELLOW. Getting to know each other. Convos to have after you’ve ‘broken the ice’ (after the ‘first dates’ stage).
BLUE. Building the potential relationship. Convos to have to deepen your connection (sprinkled throughout the dating).
BURGUNDY. Talking about your potential marriage. Convos to help you solidify your visions as a couple (right before an official commitment to marriage AKA ‘the proposal’).

These convo starters cover a range of topics and avenues to get to learn about each other.  It is not important that you cover all the questions. Rather, see these cards as a tool to jumpstart convos about important topics. The cards are not a complete list of topics to be discussed; there will be things that are particular to each of you that should be brought up.

  • What do you think of when you hear the words [words]
  • What would you rather
  • Permission to brag
  • Our similarities
  • Between the two of us, who is more likely to [do whatever]
  • What do you know about me?
  • If we were a couple, how would we [do whatever]
  • Values, dreams, goals
  • Religiosity
  • Family, upbringing
  • Money
  • Married life
  • Personality
  • Life style
  • Health


Place one card face up. Place the rest of the deck in a pile facedown.

Decide together who is first. Alternate between the two of you in choosing a question. Choose either the one that is faceup or a new one from the pile. Start your convo.

‘BOTH’ CARDS. Both of you will answer this question.  Start your convos.

The goal is to start conversations, not to just answer the questions. These are no intended to be used as an interview or interrogation.  You might find that these questions jumpstart some great convos and you cover only a few of these questions during a date.

Throughout your conversations, it is not only the answers to he specific questions that are important. Also pay attention to what is not shared, what is said between the words. The non-verbals (such as body language and how the voice is used) also can tell you a lot.



The first half an hour of the first date(s) is all about loosening up, breaking any tension and just … getting … through it. It’s important to keep things lighthearted, the conversation natural and quite general. In other words, small talk.

This small talk has an important purpose, even if it feels unimportant or meaningless. It helps build the foundation for authentic conversations and deeper relationships down the road. There is a process to building a relationship, you can't leap-frog and skip steps. You move from small to medium to big talk.

Small talk is about asking light, surface-level questions with the intent to find something in common. When you are starting a conversation, not all topics will catch on right away. When something seems to catch both of your attention, hover on that topic and dive deeper.

Others feel that it is worthwhile to get into personal conversations right away. That is personal - not private.  Personal talk might be about your opinions, your passions, hobbies, the backstory to your career choice.

In general, you can ask what feels natural for you in the moment.  Some easy ‘small talk’ topics:

  • “What did you do last weekend? What was a favorite part of your weekend?”
  • “Do you like to travel? What was a favorite trip? Have you ever been to Israel?”
  • “What do you like about your job?”
  • “Where did you spend [the recent yomtov]?”
  • “What was great memory from elementary school? What was a favorite subject in school?”
  • “Where did you grow up, and how long have you been living here?”
  • “I just read an interesting article about…”

From there, you can go into commonalities (“I also loved that subject”)  or divergent experiences (“I have always lived in this city. What was it like to move around so much?”). You might ask for recommendations (“Which country do you recommend I put on my list?”)

When you find a commonality, you might point out that you have that aspect in common. “It seems like we both care deeply about that issue.” “I sense that we both love to travel.”

You can use the A.R.E. format to move your small talk along.


  • A. Anchor: Point out something where you have a shared reality. It can even be something as simple as the place you find yourself in, or even the weather. The point is to lay a great foundation that can politely segue into a more meaningful conversation. Keep it light and pleasant. “This is a beautiful spot.” “It’s a beautiful night.”  “What is a favorite summer memory?”  


  • R. Reveal: After they respond, reveal something about yourself that builds on your original statement. “I love the architecture here.” “I look forward to the spring.”  “I loved our family road trips.”  


  • E. Encourage: Ask a question that relates to the topic to push the conversation forward. “What do you think of this place?” “Any plans to take advantage of this great weather?” “Did you ever do a road trip?”  

The rest of the conversation should be a balance between Reveal and Encourage. Through the conversation, lean more to asking open-ended questions, but don’t forget to add interesting comments.

Every conversation is an opportunity to learning something new.


People have different experiences, perspectives, insights and ideas. Ask questions to learn from the other person.  Be curious to learn something from the time you spend together.

People generally like to share their perspectives and experiences. You might ask for Advice, Insights or Recommendations.

  • “I’m trying to do [something]. Do you have any advice about how to do [whatever]?”
  • “You seem to know a lot about that topic. What books or sites do you suggest I read?”
  • “I’m looking for an app that can do [whatever]. Do you know of one?”
  • “Have you ever been [there]? What is it like?”


In addition to learning something new, this also can build the relationship. The other person gets the sense that you respect and value their insights.

People generally like to help others. Especially someone who they like.  Helping makes someone feel good (this is often called a ‘giver’s high’). Additionally, asking for help is about being vulnerable, opening up and sharing. It deepens the relationship for both the giver and receiver. 


You can ask your date to help you sort your thoughts about a topic related to your work or studies.  “Can you please help me figure this out?”


Receiving help also provides an opportunity for you to acknowledge how your life has been enriched because of them. “Thank you. You brought me so much clarity about the topic.”  “Your ideas will make this project even more compelling. I feel so much calmer about it now. Thank you.”

There is so much talking that needs to happen during dating. Some things not to do in those conversations.

  • Saying too much too early. You might think that you can create instant intimacy by spilling your guts to the other person, but it is more likely to create awkwardness between you. Your date might feel obligated to over-share as well and will probably regret it later. Save the TMI (Too Much Information) details for a later date.


  • Hijacking the conversation. 'Hijacking the conversation' means bringing the conversation back to yourself.  Don't do it. “Oh, that reminds me of a time...” Blah blah blah “You just went to Israel, I did too.  Let me tell you all about it........... ........” Blah blah blah


  • Hogging the air time. Speaking too much and not allowing the other person a chance to speak.


  • Verbal vomit. Saying whatever comes to mind without thinking it through, saying something that you really did not intend to. (Urban Dictionary)


  • Verbal Diarrhea. Droning on and on. Babbling, talking longwindedly. Speaking with no filter. (Urban Dictionary)


  • Cursing.

People like talking about themselves and their experiences, so ask questions. Every question you ask has the potential to narrow or expand the dialogue.  Ask questions as discussion starters, not an interrogation.


It's not only what you ask about, it is also how you word the questions.


  • Start with a small question, then follow up with a bigger question to build the conversation.  "Where are you from?" followed with "How is that different from this city?"  "Which city do you like better? Why?"


  • Ask Open-ended 'Why' and 'How' Questions. When you ask a 'Why' question, you explore a person’s underlying motivation.


  • Ask good questions that won’t put them on the spot, but will allow them to reveal more or less about themselves, depending on their comfort level.
  • Use questions that begin with phrases like:
    Tell me about…
    What was the best part of…
    How did you feel about…
    What brought you to…
    What’s surprised you most…
    How similar/different is that to…


  • Ask bold open-ended questions that help you get to know the person beyond the things that they do.  Avoid questions that have one-two word answers, rather aim for questions that get a conversation going.  Better questions begin with the words “What?”, “How?” rather than “Who?”,”When?”, “Where?”
    “What got you interested in computer science?”
    “How did you get involved with Chai Lifeline?”
    “What was it like for you to be stranded in that remote airport by yourself and you didn’t speak a word of the local language?”
    “What was one of the scariest things you went through?”
    “If you were given $100,000 to solve a community issue, what issue would you choose to address? What might you start doing to address that?”
    “Whose work do admire? What about it do you admire?”
    “If you could change one thing about your post high school experiences, what would it be?”

People feel more comfortable by those who match their behavior, tone of voice, talking speed, and so on. If they speak softly, mirror that and bring your own voice down a notch; if they’re enthusiastic, act similarly.


Don't mirror what they are saying. Don't repeat their observations, or just agree with them. Build on what they said. If they say, "Beautiful day" don't reply with "Yes, it is a beautiful day today." Rather, replay with  "On days like this, we used to go to the park for a picnic."  Now you have given the other person a hook to continue the conversation.


Everyone's body language provides hints to others during the course of a conversation, even if they don't realize that they are doing it. Nonverbal communications are very difficult to fake.

Moving closer or leaning in toward the other person usually shows that you are interested.  

  • Crossed arms make you appear cold, closed-off, or aggravated.
  • Slouching, moving away can indicate a lack of interest.
  • Nodding, smiling (genuine smiling) show interest.
  • Make eye contact. Looking away can indicate discomfort with what you are saying or hearing. Of course, avoid eye rolling, etc.

How someone uses their voice also communicates a lot.  Think of the volume, tone, pitch, inflections, speed.  From the way someone is speaking, we get a sense of their mood, of their level of enthusiasm.


Do your nonverbals match your words? (Also pay attention to your date's nonverbals.)

Avoid your favorite topic. ​You’ll end up talking too much and not listening enough.  You may end up getting too passionate and try to convince them onto your side.

Try to make everyone you talk with feel a little better about themselves after having met and talked to you.



Ask for their insight or advice.  And then thank them after.


Compliment them - their commitment, their sense of adventure, their curiosity.

  • "You seem so committed to that."
  • "That takes guts. Wow."
  • "It's amazing how far you got in that."


As applicable, tell them how you will incorporate their perspective or ideas into your life.

  • "That was a great word choice, I'll try to include that in my conversations from hereon."

Insert ‘hooks’ into your conversation that give the other person something to ask about or build on to continue the conversation. Don’t give the short answer, thereby forcing the other person to scramble for more questions.


If the question was "What did you do last summer?", your answer can include several hooks. "I traveled with friends to Spain. We took this awesome Kosher cooking class."  Now they can pick up on any of the hooks: travel, friends, Spain, cooking, classes.

Nexting. Following up to move from a question into a convo.

When thinking of follow-up questions, the following keywords can be used to build upon: Who? What? How? Why? Where? When? Meaning? And?

  • "I’m curious to hear your thoughts on this."
  • "And then what happened?"
  • "What is the backstory?"
  • "Has anything similar ever happened?"
  • "Can you give me an[other] example of that?"
  • "What do you mean by that?"
  • "And what else?"
  • "How does that compare to [something else]?"
  • "Can you walk me through that?"
  • "How does that play out?"
  • "Is that what you meant earlier when you said…?"
  • "What makes you say/feel/think that?"
  • "How did that make you feel?"
  • "Would you recommend that?"
  • "What was that like?"
  • "You mentioned [term or phrase]. Can you help me understand that better?"

It’s only silence. It’s your own thoughts and feelings about that silence that might make it awkward.

The conversation moves along nicely. And then there’s silence. Awkward! Or is it?  Remember, it’s only silence. It’s your own thoughts and feelings about that silence that might make it awkward.


Silence doesn’t always mean that you have nothing to say to each other.


Too often, during that silence, we think 'what is the other thinking right now about this break in the conversation'.  That makes us feel awkward about the silence.  And then when we feel awkward, what we communicate is awkward. And then it just might come out awkward.


Sometimes the best parts of a conversation are the moments of silence in between the sentences when nothing is said.


Sometimes, in those few seconds of silence – even though it may feel like it’s much longer – we reflect on what was just shared and take it in.


When you are taking the time to think of a good way to respond, to continue the conversation, or to change the direction of the discussion, then what you actually do say will be coming from a place of confidence, rather than the awkwardness of trying to fill that silence.

Be comfortable in that silence.

Be confident in that silence.

And you’ll project comfort and confidence in yourself.

Put your phone away.  Nothing says "I'm not totally with you" like looking at your phone.

 Choose locations that have minimal distractions. The point is to have meaningful conversations. Do what you can to set that environment.  

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