Dear Penina,
I’m at a loss about how to help my younger sister with shidduchim. I believe my parents are making serious mistakes, but I’m not sure if or how to tell them—they’re easily offended and hold grudges. The problems show up at two stages of the dating process.
First, they’re really misguiding my sister through the process. They have a specific vision for what they want in a son-in-law that doesn’t match who she actually is, neither in hashkafa nor personality. They keep steering her toward young men who aren’t right for her, then wonder why all her shidduchim end after one or two dates. Meanwhile, my sister needs some guidance to figure out what she’s actually looking for in a husband, plus some help with basic dating etiquette and skills.
Second, they meddle way too much and have caused problems when she was actually dating someone. Once, when a young man came to pick up my sister, my father asked him to give a dvar Torah on a parsha we’d read three months earlier. Another time, my mother ordered pizza right before a first date, and when the young man arrived, she insisted they all sit down to eat before going out. I love my family and want to help, but I get the sense they’re not open to feedback. I want to connect her with people who could guide her, but she follows their lead and thinks it’s not necessary.
Sincerely,
Helpless
Dear Helpless,
Your question captures an age-old dilemma: how to help people who don’t realize they need it and have made clear they don’t want your interference. It’s especially frustrating when it involves your inner circle. You’re watching your sister’s chances being hurt by factors she doesn’t understand, and it’s painful. Your primary challenge is that unsolicited advice risks pushing away the very people you want to support—which is why you need to tread carefully.
Look for ways to support her without directly confronting your parents. Suggest a sisters’ shopping day and ask if she needs anything for dating. This opens the door for important conversations, making yourself available to hear her out during this process. Suggest a shidduch to her yourself—even if she doesn’t accept, it signals that you’re there to help guide her and clarify what she’s looking for.
About the meddling: It sounds like your parents see outside help as a threat to their authority or a critique of their competence. Maybe you can gradually step into a role that feels like “sisterly bonding.” By asking open-ended questions about what she wants—rather than telling her what she should do—you’ll help her develop her own voice, which she’ll eventually need when standing up to your parents.
If there’s a trusted rav, rebbetzin, or older relative your parents respect, they might be able to suggest a more objective approach to her dating. Sometimes an outside voice carries more weight than a daughter’s.
Ultimately, remember that Hashem is the true shadchan. While we’re required to make reasonable efforts, our results don’t dictate the outcome. Find a way to accept what you can’t change. If your parents refuse to budge, your role may shift from fixer to supportive sister who loves her exactly as she is. Do your part, keep davening, then try to release the heavy burden you’re carrying. You can be her greatest advocate by simply being the one person in her life who offers love without pressure or rigid expectations.
Wishing you clarity and peace,
Penina
Penina Flug, LCSW, has dedicated over two decades to helping individuals, couples, and families. She received her master’s in social work from Fordham University in 2003 and advanced training in Emotionally Focused Couples Therapy (EFT) in 2015. Her private practice focuses on relationship therapy and premarital education. Flug is also a passionate advocate of premarital education within the Jewish community and contributes to the field by training premarital educators, including kallah teachers. She can be reached at penina@peninafluglcsw.com.