22 Sep Dating and Relationship Advice

Dear Rabbi and Shira, 

I am a single 28 year old man. I am the “black sheep of my family.” My family is very Yeshivish and my siblings have all gone to learn in kollel. I have chosen to go to college and pursue a career in business. As I was the top of my class in Yeshiva my parents don’t respect what I’m doing and it’s tearing my mother apart. I often find her crying. The question is in terms of shidduchim my family is a prominent family in the community and I can’t seem to break free of the stigma that I am modern and off the Derech. I go to minyan everyday and make time to learn daily. The shadchanim either say they don’t know anyone for me or keep setting me up with modern girls. I don’t view myself that way. How will I ever find someone for me if the community doesn’t understand who I am? 

-Boxed in in Brooklyn 

Dear Boxed in, 

We’re sorry to hear about the trouble which you are having. You have been true to yourself and chosen a path, one in consonance with Torah and Mitzvos, but one which is a little different than your family. Ashrecha, that you have the strength to live within your convictions. You have consciously made decisions regarding every part of your life. Each step has been with nuance, combining the highest of ideals with the realities of life. We hope that you’ll find someone as measured, balanced and thought out as you. We’re sure your parents will continue to have nachas from you. When the dating process becomes difficult, frustrating and worrisome for you, take time to take a deep breath. Take moments for self-care, and relaxation. You’re looking for a specific person who is looking for you. This difficulty in finding your spouse is present “across the boards” even for people who “fit in the box.” Please don’t beat yourself up in selfdoubt. The first practical piece of advice that we’d give, is to diversify your shadchanim. Each shadchan has a social circle in which they are drawing people to set up. If the shadchanim are all drawing from a similar group, that’s not necessarily going to find a match for you. Try to meet with matchmakers who are involved in different communities. You’ve heard it before, diversify your portfolio! Second, when you meet with shadchanim, accept that people often lack nuance, therefore, give them feedback to explain to them what they are getting wrong. At first glance, it would seem to them that you are either “Yeshivish or “Modern.” Spend time explaining to them what your life and world is like. This will allow them to be more targeted in their selection of possibilities for you. Invest the time in getting to know your shadchanim. Third, we believe that it is time to consider using dating websites or attending singles events. These will allow you to represent yourself and your views accurately and adequately, and be able to filter out people who are not on the same page as you. This will give you some more power over your process and be able to take your own destiny back in your hands. Fourth, is to daven. Remember that our actions only can add up to so much, and a lot is in the hands of the Orchestrator of the World, the Shadchan of Shadchanim. Hatzlacha Rabba, and a Gmar Chasima Tova,

-Rabbi Reuven & Shira Boshnack