Dating with clarity and intention is one of the most powerful ways to approach the Shidduch journey. Use this guide to get you there!
While emotions can be strong, it’s essential to also reflect practically and spiritually. This guide was designed to help girls assess the character, values, and compatibility of the boys they are dating — not to judge, but to clarify what feels right, and what aligns with their vision for the future.
Below you’ll find guided questions and prompts grouped by topic to help you gain deeper insight during your dating process or even before it begins.
Character and Middos: Who Is He at the Core?
- Is he generally a happy person? What makes you think so?
- What kinds of things frustrate or anger him?
- How does he handle disappointment or stress?
- Does he seem flexible or able to be mevater (yielding)?
- Are his comments about others usually positive or negative?
Tip: The way someone speaks about others is often a window into their values and emotional health.
❤️ Your Relationship With Him
- Do you feel emotionally safe around him?
- Do you trust him?
- Do you respect him — and feel that he respects you?
- Can you communicate freely about deep or sensitive topics?
- Are you able to be yourself around him?
- Are you attracted to him on an emotional and physical level?
- Does he express appreciation or admiration for you in a healthy way?
- How does he speak about your family and friends?
- Are disagreements handled respectfully? Can you “fight fair”?
- When miscommunications happen, how does he respond? Do you end up blaming yourself?
🏠 Fitness for Marriage
- Can you see him confidently taking on the role of a baal habayis?
- Does he demonstrate competence and follow-through?
- Is he financially responsible or aware?
- Does he drive safely and respectfully?
- Can he accept your input or direction without defensiveness?
Interpersonal Relationships: How Does He Treat Others?
- How does he speak about his parents and siblings?
- Does he have a close relationship with a Rebbe or mentor? Why that one in particular?
- Has he ever been given challenging guidance? How did he respond?
- Does he have healthy friendships?
- How does he relate to older family members (e.g. grandparents)?
- Has he ever had a difficult roommate or peer? How did he navigate that?
- Who does he turn to when he needs to talk?
📍 Future Plans and Vision
- Where does he imagine raising a family — and why?
- What are his career or Torah goals: Chinuch, business, Rabbanus?
- Are you comfortable with and supportive of his vision?
- Do his long-term goals align with your values?
🕯️ Hashkafos and Values
- What does he consider a bad middah?
- How do you know he has real Yiras Shamayim?
- Is he cynical about Yiddishkeit, Rabbanim, or frum institutions?
- How does he talk about less observant Jews or non-Jews?
- Has he ever taken on personal challenges for spiritual growth?
- What is he most proud of accomplishing?
- How does he spend his free time — Friday afternoons, Motzei Shabbos?
💬 Beliefs About Marriage and Family
- How does he view the role of a working mother vs. stay-at-home mom?
- What are his feelings about your education or career aspirations?
- Would he be comfortable helping with household tasks or childcare?
- Does he value partnership in daily family life?
🌱 General Compatibility
- Are you comfortable with his tone, language, or how he expresses emotions?
- Are you okay with how he dresses and presents himself?
- How extroverted or introverted is he? Are you comfortable with that?
- Is he appropriately friendly with strangers?
- What does he enjoy doing during Chol Hamoed or family trips?
- Would you feel proud to walk next to him in public or introduce him to those you respect?
- How do you see him fitting into your family dynamic?
- Are there aspects of your family life that he may need to adjust to?
In Conclusion: Don’t Just Ask — Reflect
These questions are not a test, nor are they meant to create doubt. They’re here to help you gather information, process your experience with clarity, and stay true to your emotional and spiritual instincts. Sometimes the answers come easily, and sometimes you’ll need time, conversations, and Tefillah to gain clarity.
Dating isn’t just about checking boxes. It’s about building a foundation for a life of mutual respect, growth, and shared values.
