Dating is a deeply personal and sometimes overwhelming experience. In the world of shidduchim, it’s not just about chemistry — it’s about compatibility, values, and long-term potential. This guide is designed to help boys gain clarity as they navigate the dating process. Whether you’re getting to know someone or assessing your current relationship, these reflective questions can help guide your thinking and decision-making.
Basic Character Assessment
Understanding your date’s personality and emotional makeup is foundational. Ask yourself:
- Does she seem like a happy person? What makes you feel that way?
- What types of situations upset her? Does she handle stress with resilience?
- Is she able to process frustration or anger in a healthy way?
- Does she speak positively about other people?
- Is she flexible and capable of giving in when needed?
- Can you count on her? Is she someone you feel you could rely on?
- Would you describe her as a giver? Or does she come across as “high maintenance” or entitled?
💬 Your Relationship Together
Building a meaningful relationship means being honest about how you interact and feel around each other.
- Do you trust her?
- Does she respect and look up to you?
- What do you admire about her? What does she seem to admire about you?
- Is either of you hoping the other will change after marriage?
- Can you truly be yourself with her?
- Do you feel she “gets” you?
- Are disagreements manageable? How do the two of you work through conflict?
- When there’s a misunderstanding, does she take responsibility, or is blame one-sided?
- Are you able to problem-solve as a team?
- Do you enjoy her company?
- Are you physically and emotionally attracted to her?
👥 Her Relationships with Others
A person’s interactions with friends and family can be revealing:
- How is her relationship with her parents and siblings?
- Are you comfortable with the type of friends she has?
- Has she had difficult roommates? How did she handle those situations?
- Does she have a mentor or Rav she stays in touch with?
Hashkafic Compatibility
Spiritual alignment is a cornerstone of many successful marriages:
- Are you on the same page regarding tzniyus and dress standards?
- Have you discussed the kind of home and community you’d like to build?
- What are your shared visions for your children’s education (e.g., Yeshivos, Chinuch)?
- Are your views aligned on media, technology, and internet usage?
Personality Compatibility
Even the best couples experience tension — what matters is how you manage it:
- Are there any habits or traits that bother you?
- Are there things you’re hoping she’ll change?
- Does she seem to need more emotional attention or time than you might be able to give?
- How does she spend her downtime?
- Do your strengths balance each other out? Can you help each other grow?
🍼 Marriage & Motherhood Readiness
Consider the day-to-day aspects of building a life and raising a family:
- Is she patient, kind, and good-natured?
- Is she open to learning and growing as a wife and mother?
- Can she live within a budget? Do you see signs of financial responsibility?
- If long-term learning is your goal, would she be content with a simpler lifestyle?
- Does she appear organized and productive?
- Have you discussed shared responsibilities around childcare and housework?
- Does she have experience with children?
- Has she been involved in Chessed or volunteering?
👗 Style & Self-Presentation
While outer appearance isn’t everything, it does matter in the long term:
- Do you like the way she dresses?
- Does she put too much or too little emphasis on her appearance?
- Are you comfortable with how she expresses herself?
- Is she too loud, too shy, or somewhere in between?
- How friendly is she with strangers — and are you okay with that?
🎯 Goals, Ambitions & the Future
Make sure you’re aligned on both lifestyle and long-term dreams:
- Does she have strong preferences about where to live (e.g., near her parents, in Eretz Yisroel)?
- Do you agree on how long you should stay in learning?
- If she supports your learning, does she have a viable plan to earn a living?
- Are you comfortable supporting her through a degree or training program?
- Have you discussed whether she plans to be a stay-at-home mother or pursue a career?
👨👩👧 Family Dynamics
A successful marriage often involves building bridges between two families:
- How do you feel about her family? Could you stay with them for Shabbos or longer stretches?
- Does she seem emotionally independent from her parents?
- Is she comfortable with your family — and how do they feel about her?
Final Thoughts
Dating is not about passing a test — it’s about discernment, honesty, and introspection. These questions aren’t meant to create anxiety, but to empower you to think clearly about the person you’re getting to know. A successful Shidduch is built on shared values, mutual respect, emotional intelligence, and Hashem’s guiding hand.
If you find yourself uncertain or overwhelmed, don’t hesitate to reach out to a mentor, Rav, or trusted advisor. Your future is worth the investment.
