Dear Shoshy,

I just went on my second date with someone, and he told the girl who set us up that he wants to “break shadchan.” In other words, he no longer wants to go through her and report to her about how each of our dates has gone, rather he thinks we are ready to discuss this and potentially end the courtship face-to-face. However, I am not sure I am ready for this so soon in the process. I have never “broken shadchan” this early on and I do not yet feel comfortable discussing our relationship with this boy himself. I am hesitant to tell my friend that I am unready to “break shadchan,” for fear of hurting the boy’s feelings. If he feels we have already hit that mark, perhaps I should allow my friend to be taken out of the process. On the other hand, do I want to risk the potential of having to break up with him after our third date, face-to-face, when I hardly know him?

Thank you for your help,

To Break or Not to Break

Dear To Break or Not to Break,

It sounds as though you have found yourself between a rock and a hard place. During the dating process it is important to make sure you always feel comfortable. That being said, the other person’s comfort is important as well. I understand the awkwardness of speaking to someone so early on in the process about ending it, or any of the other details he might want to discuss. It is unfortunate that the two of you are not on the same page and that he seems to want to speed things up a bit.

You also may feel uncomfortable at the prospect of having this boy know that you are not on the same page as him. However, you need to ensure that you are expressing your feelings in the correct manner and giving him the proper indication of where you think this is going. Therefore, I think it is important for you to assert yourself with your friend who is the go-between. Tell her how you are feeling and that you are not in the same emotional space as the boy. If you want to ease the awkwardness, maybe ask your friend if she can tell the other party that she thinks it’s a bit too early and that she doesn’t think it’s the proper time for her to be taken out of the equation. Alternatively, you may want the boy to know that this is coming from you and that you are not ready to discuss your feelings with him. Good luck!

Im yirtzeh Hashem by you,

Shoshy Goldstein

Shoshy Goldstein (a pseudonym) is in the “dating parsha,” but she has great intrinsic instincts that her friends and family members have sought out when they have questions about dating etiquette. Ask Shoshy your own questions by emailing [email protected]. Disclaimer: This column is not intended to replace professional advice.