Shidduch dating can be both exciting and daunting. Whether it’s your very first date or you’re already a few in, finding the right things to talk about is key to building a comfortable, meaningful connection.
Not every date flows naturally—and that’s okay! Sometimes, all it takes is a thoughtful question or a creative prompt to spark a great conversation. This blog post breaks down ideas for every stage of shidduch dating: from fun ice breakers to deep, hashkafic discussions.
First Date Ice Breakers
Starting a date can be awkward, especially when you’re still warming up to each other. These light and engaging questions can help break the ice and open the door to more natural conversation:
- Who is the most fascinating person you’ve ever met?
- What’s an accomplishment you’re really proud of?
- If you never had to work again, how would you spend your time?
- Describe your perfect vacation.
- What are you best known for among your friends?
- What trend or fad never made sense to you?
- How do you unwind after a long day?
- What’s a fear you’ve had to face?
- What’s a wrong assumption people often make about you?
- Do you prefer to work alone or as part of a team?
- How have you changed since high school?
- Do you rehearse phone calls before making them?
- What are you most grateful for?
- If sleep wasn’t necessary, how would you use the extra time?
- What have been some of your happiest moments in life?
- What’s the most spontaneous thing you’ve ever done?
Creative Conversation Starters for Any Stage
If the conversation needs a little boost or your date isn’t much of a talker, try one of these fun and thoughtful prompts:
- What’s the most interesting experience you’ve ever had?
- Want to play Jewish Geography?
- If you did a PhD, what would your thesis be about?
- In your wildest dreams, what would you love to do?
- What’s the best book you’ve ever read?
- Is there an article or idea that really stayed with you?
- If you were stranded on a desert island, what three things would you take?
- Best restaurant you’ve ever been to?
- What’s one summer you’ll never forget?
- What drew you to your career or area of study?
- What’s been your best birthday celebration?
Shidduch Questions for Ongoing Dates
As you go out more and start to build familiarity, your questions can gently move toward more personal and revealing topics.
Dates 3–5: Building Emotional Insight
These questions help uncover personality, motivation, and worldview:
- What energizes you?
- What makes you angry?
- Who or what has impacted you the most in life?
- What inspires you regularly?
- What’s your greatest strength—and biggest weakness?
- Where do you stand on social or political issues?
Dates 6 and Beyond: Exploring Compatibility
When you’re thinking more long-term, it’s important to talk about compatibility and vision for the future:
- What qualities do you look for in a future spouse?
- What types of personalities do you get along with best?
- Have you visited Israel? How did it affect you?
- What’s your taste in décor, music, food, and clothing?
- What would you love to learn more about?
- What life accomplishment makes you proudest?
Deep Dive: Hashkafic and Life-Oriented Topics
Once you’ve built enough trust, deeper discussions about values, goals, and lifestyle can help determine true compatibility. Consider exploring:
- How do you build and maintain friendships?
- What are your family dynamics like? Who are you closest to?
- How would you like to raise future children (bezH)?
- What role does chessed play in your life?
- How do you see household responsibilities being shared?
- What place does Torah learning have in your day-to-day life?
- What are your core life values and priorities?
- How do you imagine Shabbos and Yomtov in your future home?
- How have you dealt with life’s challenges and grown from them?
- How do you resolve moral dilemmas or conflict?
- What do emunah and bitachon look like in your everyday life?
- What are your non-negotiable red lines?
- How do you see yourself supporting and relating to your spouse?
- What are your views on finances and money management?
- How would you describe your level of religious observance?
- What lessons would you take (or not take) from your parents’ marriage?
- How would you handle disagreements or stressful situations in marriage?
- What’s your stance on technology in the home?
- How important is living in a strong community to you?
Final Thoughts
Shidduch dating isn’t just about compatibility on paper—it’s about connection, shared vision, and the ability to communicate and grow together. Whether you’re easing into conversation or diving into deep values, having thoughtful questions at your fingertips can help you move forward with clarity and confidence.
