6 Honest Questions Shidduch-Age Bochurim Have

The summer is winding down and everyone will soon be returning to life as usual (only to be briefly interrupted by Tishrei in a few short weeks). With this comes a new cohort of bochurim and young ladies preparing to start their journey in shidduchim. This stage can be met with excitement, anxiety, or anything in between. With so much focus on the challenges young women face in shidduchim, the struggles bochurim have are often overlooked.

One thing is for certain: every bochur has thoughts, feelings, and opinions about this new chapter. Most understand the significance of beginning shidduchim and realize that the decisions made during this time will likely shape the course of the rest of their lives. Many carry big, important questions about themselves and about the process. While some bochurim are fortunate to have parents, mashpiim, and friends in whom to confide, many others are confronted with insecurity, confusion, shame, and fear.

To help bochurim think through and begin to resolve some of their concerns, I want to share a selection of the many questions I am often asked, along with my thoughts on each one. My hope is that by presenting these questions and responses, more bochurim will find support and clarity as they navigate shidduchim — whether they are just starting out or have already been dating for some time.

1. I am set up to go out on my very first date, but every time I think about it, I start to feel very anxious. How should I deal with my anxieties?

Welcome to this brand new stage of life. If you’re like most bochurim, you haven’t had much preparation for the practical realities of dating, so no wonder you’re anxious! Anxiety is a G-d-given signal that something is important and consequential.

Your task is to sit with the anxiety and explore it. What about dating worries you? Is it that you might behave awkwardly with a complete stranger (who is a female no less!)? Being caught off guard? Having to share something personal? All of these are legitimate concerns. But remember: you don’t need to be prepared for all possibilities before your first date. The purpose of a first date is really just to answer one question: Can I spend a few hours with this person and enjoy her company as we break the ice?

If even that feels overwhelming, you can call it out honestly. For example, you can say, “This is new to me and I sometimes get nervous in new situations, but I’m looking forward to getting to know you.” Just acknowledging the reality of how you feel in the situation can go a long way toward putting your nerves at ease.

2. Do I need to know what I will do for a living before I start dating?

In secular culture, financial security is often valued above family life. In the frum community, family life usually takes precedence. That does not mean a financial plan isn’t important — it certainly is — but having a career locked in before you begin dating is neither expected nor realistic.

What matters most is having direction. Do you know your skills, strengths, and passions? Have you begun to explore how to use them productively? Are you ready to make the commitment and accept the responsibility of supporting your family? When you date, let these ideas be part of your conversations. As things become more serious, discuss them more openly and see whether you share the same values. The right match will respect your career path and stand beside you with support and encouragement.

3. I have seen things on the internet that I know I shouldn’t have. Is there hope for me to build a true connection in marriage?

This is a sensitive question, one that’s easy to look past. But ignoring it won’t make it go away. The unfortunate reality is that most men today have been exposed to harmful material online.
The first thing to know is that you are not alone. Many other bochurim are struggling with the same issues and there are rabbonim, mashpiim, and therapists who can compassionately help you. What matters more than the degree of exposure is how it has affected you. If you find yourself unable to control your technology use and what material you consume, that is a larger challenge. If you’ve taken steps to guard yourself and move forward, you are already on a healthier path.

Having someone you trust to confide in about your specific challenge is critical. With the right support, you absolutely can build and sustain a true, long-lasting connection with your future wife.

4. I’m actively working on myself so I can be ready to date, but I’m feeling pressure to begin and not wait. What should I do?

It’s admirable and commendable that you are investing time and energy into your growth before dating. Reflecting on yourself and committing to taking important steps toward bettering yourself as a man and a frum, chassidishe bochur will surely pay off as you go forward in life. Too often, young men skip this step or assume they can “figure it out on the way.”

The world we live in today has so many pressures, distractions, and challenges. This reality demands that a bochur be very intentional in his approach to shidduchim. Each individual has his own issues to address; some larger and some smaller. If you know you need time, take it. But don’t confuse readiness with perfection because the latter is neither achievable nor the ideal. Identify the areas you need to work on, set a plan, and give yourself a realistic timeframe.

Talk to your parents about where you are holding. Let them know that you are working on yourself to be able to enter shidduchim with the correct mindset.

5. I have gone out with a few young ladies whom I liked, but after a few dates they didn’t want to continue. Am I doing something wrong?

Nevertheless, there are ways that the nicest, most suitable potential husbands can show up to a date that can result in a young lady looking elsewhere. Make sure you plan the dates well. Know where you are going and have some familiarity with the spot (looking at pictures online or asking friends who have been there may be enough). Be present; the young lady who is sitting across from you is there to get to know you. Your phone should be silenced and out of sight. Get curious about her, show interest. If you’re going out for a 2nd, 3rd, or 4th time, reflect beforehand on what you would like to delve deeper into about both yourself and her. Be decisive, respectful, and confident.

This is a painful situation, especially when little or no feedback is given or when the explanation seems too diplomatic or vague. While rejection is rarely easy, it doesn’t automatically mean you are doing something “wrong.”

That said, there are ways to ensure you show up well: plan dates thoughtfully, be fully present, silence and put away your phone, and show genuine curiosity about the other person. Reflect on what more you’d like to share about yourself and what you’d like to learn about her as dating moves forward. Be confident and decisive, and always be respectful. Remember: sometimes a shidduch simply isn’t the right match, and that’s okay.

6. I’m hesitant to get married because I’ve seen so much dysfunction in marriages around me. What’s your advice?

This is an honest and important question. Witnessing dysfunction — whether neglect, poor communication, or abuse — can be painful and leave deep doubts.
What your experiences might have hidden from you is how much beauty, joy, and growth a healthy marriage can bring. Your awareness of what doesn’t work can be an asset if it pushes you to learn what does. Spend time with families who function well. Observe, ask questions, and read about healthy relationships. Seek mentors who can model what it means to be a healthy husband. Your past experiences do not define your future.

Marriage, when approached with care and commitment, can be a source of brachah, fulfillment, and profound growth.

***

The journey of shidduchim has its challenges — sometimes practical, sometimes deeply personal. Each question is an opportunity for growth, reflection, and clarity. No bochur should navigate this path without guidance. With mashpiim, rabbonim, therapists, and trusted family and friends, every young man deserves the support he needs.

Rabbi Dr. Dovid Brownstein is a licensed psychologist and the facilitator of the Beyond Breadwinning workshops, designed to help bochurim in shidduchim or engaged prepare for marriage with confidence and clarity. For more information about upcoming workshops, visit beyondbreadwinning.com. You can reach Dr. Brownstein by email at [email protected].