Dear Dating Coach,
My family is really close with a few different families in our neighborhood. Of those families, one has a daughter that I really like. I went to yeshiva and I am not in the habit of talking to girls that I am not dating, but I am definitely interested in her. When we attend mutual events, I can see how she interacts with others – warmly and kindly. She has a great laugh, and is always helping her younger siblings. She is beautiful to me, and she seems so confident. I have spoken to my parents about reaching out to hers or making the connection through a shadchan, and they think it’s a great idea. But I’m scared. What if she says no outright? What is she is completely not interested? Or if we do go out and she doesn’t like me, then it will forever be awkward between our families! I want this to work very badly, but is it worth the risk?
Risk Averse
Dear Risk,
My lovely neighbor just gave us a box of chocolates for Shabbos that came with a handy illustration sheet that explained what each piece was. There was butterscotch, milk chocolate ganache, hazelnut, coffee bean, and the dreaded macadamia nut. The next morning, the sheet mysteriously disappeared, but the box was still offered at dessert. It became very quiet as everyone contemplated the box with intense concentration. No one could remember which chocolate held delicious caramel and which one carried the menacing macadamia. (Too dramatic? Maybe.) They peered, hoping for x-ray vision, they “ennie meenie miney moed,” they reached out and retreated, and they sniffed the air like hounds. Finally, the table agreed to take the risk. Everyone held their piece and took a bite. Needless to say, the reaction was positive, minus the macadamia winner who vowed to never eat chocolate again with us…until the next box arrives.
If At First…
I hear you. Taking a risk is scary. You know a wonderful girl, and like what you have seen. You have spent enough time in her company, albeit in larger groups, to know that you are interested in a deeper connection. You are worried that she will not be interested, perhaps she will even scoff at the idea of “you and her.” You are concerned that even if you are blessed with a “yes,” she may not like you after getting to know you better, and awkwardness with descend on both of your families forever and ever.
You Don’t Succeed…
You spoke to your parents, asked for their opinion, and they agreed that this was a good idea. This tells you that others can envision what you see so clearly; that there could be more, even a potential future. You are not dating her now. If she is asked and is not interested in going out with you, you will still not be dating her. If she is asked, and goes out with you and then decides not to continue, you will also not be dating her. Therefore, the worst result for you, puts you in the exact situation you are already in; not dating her. Nothing ventured, nothing gained, literally. I agree, that there is potential for some discomfort, but that would dissipate naturally over time.
Don’t Skydive.
What if she says yes, however, and you go out and birds sing, the clouds part, the sun shines, and you get married and have a beautiful family? What if she has been feeling the same, but has also let the fear of rejection hold her back? What if you are perfect for each other, and only apprehension stands in your way? Sometimes, that risk offers you the best chocolate in the entire box.
