Photo Credit: Jewish Press

Dear Dating Coach,

I am 22 years old and have been dating for a short time. I am from the type of family that would expect their daughter to find their bashert through the shidduch process and I am the kind of girl that looks like she would follow that route as well. But a few months ago, I went to a Shabbos meal by a newly married friend and she had a bunch of singles at her meal. One of the guys there started talking to me and we took a long walk after the meal. Then he reached out after Shabbos and we started spending a lot of time together. Long story short – I think he is the right guy for me, but my parents have no idea I have been dating him! I need to tell them, but I am terrified that they are going to be really angry. I think they would like him, but I need a full-proof way to get them on board. Please help!


Scared Single


Dear Scared,

True Story. You can Google it after Shabbos. I read recently that a young boy in Africa standing at the water’s edge was surprised by a hippopotamus who swallowed him whole. Surprise! A quick-thinking good Samaritan attacked the hungry hippo, who miraculously released the boy unharmed. Surprisingly, when the boy’s panicked parents arrived, he was heard yelling, “best surprise ever!”

Nope, that did not happen. Not even close. He is likely in therapy right now.


Surprise Me! Not.

Thank you for your letter. You met someone in an unexpected way. You planned to date only through a shadchan and this was certainly the expectation of your family as well. Yet, you are now dating someone that you connected with at a Shabbos meal and you hope to plan a future with him. Your parents however, do not know and you are worried about their reaction. You want them to accept him and to celebrate with you, but you are not sure how best to approach them. Is there a way you wonder, to disclose that you have been dating someone secretly in a way that might minimize an adverse reaction.

Let’s be real. Even if we begin with the assumption that this guy is perfect for you in every way, it is highly unlikely that your parents will be accepting from the start. “You have been dating someone we know nothing about secretly for months and want to marry him? That’s terrific!” – Said no parents ever. So, to begin you must expect that they will feel blindsided and shocked; a feeling that often showcases big reactions and emotions. To expect them to smile and nod and then pull out their checkbooks to plan a vort is not only unrealistic, it’s also self-centered and immature.

Instead, ask your parents if they can meet with you privately. Tell them you have something to share with them and then calmly relate the truth. Apologize for not being forthcoming until this point and take ownership of this slight and the hurt your secrecy will have caused them. Be prepared for their shock, for their anger, and for their questions. Remain respectful throughout the conversation. Then be prepared to offer concessions. If they would like to find out about him though their community friends, agree. If they would like to meet him, agree. If they would like you to slow down so they can feel more comfortable, agree. Finally, as hard as this is going to be – listen to the feedback they offer you. You are already emotionally invested in someone that your family has not researched or vetted. There is a reason families appreciate the shidduch process, and you have rejected it. If information arises that is of legitimate concern, take the time to make sure that you are making the right decision with the help of your family, a trusted mentor, rebbetzin, or a dating coach.

Surprises are not always easy. Be patient, accepting, and open-minded in sharing your information, and only then can you hope that your family receives the information in the same way.


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Henni Halberstam is a Dating and Marriage Coach whose expert advice will help you navigate dating and relationships in order to ensure a successful marriage. You can contact her at to schedule a phone session.