Question
I’m dating this guy, and we have a lot in common. However, I’m unsure about how serious he is when it comes to Yiddishkeit and Hashkafa. How do I bring this up without it sounding like an interview or interrogation? Any thoughts?
Answer
It all starts with your mindset. Are you approaching this conversation with genuine curiosity, or do you feel like you’re conducting an interview? Your tone and choice of words will naturally reflect your intention. Remember, these discussions are what shidduch dating is truly about—open and honest communication about values and life goals. Instead of waiting for the topic to surface organically or dropping hints, it’s important to address it directly in a natural, flowing way.
Approach the conversation with curiosity and an open mind rather than a rigid checklist. Instead of thinking in terms of whether he “ticks all the boxes,” focus on truly listening and understanding his perspective. Afterward, reflect on whether your visions align and whether you can respect his approach, even if it doesn’t perfectly match what you initially thought you wanted. The goal isn’t to find someone who matches your exact vision perfectly. It’s about discovering how your values and life goals can intertwine.
Maybe you envisioned being married to a man who has three shiurim a day and this guy has two; it may be that his two shiurim are really quite deep and meaningful. Or, maybe he currently learns four hours, but he recognizes that he will learn less when he is working to provide for a family. Instead of focusing solely on the specifics of what he’s doing right now, talk about why certain aspects of his life matter to him and how he envisions things changing in the future. And of course, share your own values. This will give you insight into whether your broader goals align, even if the details don’t match perfectly.
You can start the conversation by setting a positive tone by saying something like, “I really value building a home with shared goals and values, so I’d love to hear your thoughts on what that looks like for you, and I’m happy to share mine too.” This makes the discussion feel more personal and mutual rather than a one-sided interview. It opens the door for a conversation that feels balanced and collaborative.
You can start by talking about the general atmosphere you want in your home, and then talk about different aspects. For example, you could say: “What I love about how I grew up is… for example, my father did… my mother did… and Shabbos was a special time because…” This opens up the conversation in a natural, personal way. Providing specific examples can help him better understand your outlook and why certain values are significant to you. This personal sharing can foster a deeper connection and invite him to open up as well.
When it comes to specific aspects like learning, Shabbos, or music, the key is to bring them up in a way that doesn’t feel like you’re ticking off a list. Instead of asking, “How much do you learn each day?” you could say, “Learning is really important to me for a Jewish home and family. How do you see learning fitting into your life and family? What does that look like for you?”
Keep things conversational and engaging by asking open-ended clarifying questions, such as: “When you say you want to learn all day, what does that actually look like to you?” “When you say ‘for a few years,’ what timeframe are you thinking?” “Is there a family you look up to and would want to model your own after? What is it about their home that resonates with you?” These types of questions encourage a deeper discussion while keeping the conversation natural and pressure-free. They also provide insight into his values and future aspirations.
As the conversation progresses, summarizing what you’ve heard can be helpful: “So, from what I understand, you’re saying XYZ. Am I getting that right?” This invites clarification and reassures him that you’re genuinely listening. It’s an opportunity to deepen the conversation and ensure you both are on the same page.
Most importantly, remember that you don’t need all the answers from just one conversation. These discussions are part of an ongoing dialogue, and if you’re still unsure after one date, that’s completely okay. Let the relationship unfold naturally, allowing time for both of you to keep learning about each other without the pressure of having everything figured out immediately. Circle back to this topic if you have any other questions or need clarification along the way.
Ultimately, these conversations are about understanding each other’s values and seeing if they can intertwine. By focusing on the ‘why,’ ‘how,’ and ‘what,’ you can have a meaningful discussion that sets a strong foundation for your relationship. Take your time, and be open to hearing different perspectives so you can both feel comfortable moving forward together.
