Photo Credit: Jewish Press

Dear Dating Coach,

As an older single I have been told to expand my options and I have tried to be very open to possibilities. So, when a single father was suggested to me, I said yes even though I previously refused to go out with men who had children. We have gone out for a while now and we have really connected. I like everything about him and we started to discuss an engagement. Then, I met his daughter. She is adorable, don’t get me wrong. But suddenly the challenge of introducing her into the mix, the responsibility, and the “step-parent” role became very real. I don’t know if I can do this anymore. I am so conflicted! He is amazing and I want to marry him, but I am not sure I accept the whole package.




Dear Step,

I once went hiking with my cousins. We walked and walked for hours (67 minutes) and traversed the rugged terrain (there might have been a rock). We were determined; armed with our hiking boots (converse high-tops), our walking sticks (broken branches), and our equipment (sunscreen). We climbed higher and higher, growing more fatigued with every step. My cousin sat down and urged us to continue on without her. ‘I can’t continue, this is more than I bargained for.” We reminded her of the view waiting at the top, of the sense of accomplishment she would feel, but still, she would not get up. “How about one step?” I asked. Just one step. She stood up and took a step. Then she took one more, and one more after that. Very quickly we reached the peak. The view was breathtaking; the challenge suddenly small, as we stood in awe of nature’s beauty and the gift we had been given.



You are clearly brave. You opened yourself up to possibilities and one found you. You found someone that you want to marry, but when you met his daughter, your old doubts and new worries surfaced. This is a challenge and not one that can be dismissed. It is a big responsibility to include a child into a new marriage, and of course you have concerns. You want to be successful in your future marriage and your new added role and you are not sure that you will be.



Reach out to those who can guide you. A Rebbetzin, a wise family member, or a therapist who might offer you advice moving forward. They can give you guidance on navigating a role you find daunting, and can offer tips and act as a sounding board when you feel overwhelmed. Be open with this special man, communicating your concerns so he can validate, problem-solve, and reassure you. Work together to assess your comfort level, his, and hers. Your willingness to “try” will be meaningful and precious to him.



Remember, a child is forever, but today you don’t need to figure “forever” out. Today, you only need to take one step forward. Focus on small tasks as you work your way towards a larger goal. Spend an afternoon with his daughter. Focus on connection. Then spend a whole day. Accept that this mountain won’t be without challenges, and be kind to yourself through the process. If you are willing however, to take one step at a time, you may walk yourself toward a wonderful future.


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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 [email protected] to schedule a phone session.