Dear Shoshy,

I recently went on a first date with a boy and left the date feeling unsure how to proceed. I generally go on second dates as a rule in order to give the person another shot. However, I left this date unsure if I wanted to do so. The boy I went out with seemed perfect for me on paper, before I met him. Our hashkafas aligned, we were interested in the same things, he was a few years older, which I generally think is better for me, and we run in similar social circles. I was excited to meet him since it seemed like we had so much in common. However, when we were on the date, I felt as though he was more interested in himself than he was in me. He spent the majority of the time describing himself and presenting his life’s accomplishments. He was in semicha and told me that everyone always called him assuming that he would know the answers to their halachic questions, although he had not yet reached that status. He enjoyed boasting about his frumness and letting me know all the different details of his past. I tried to stay engaged in the conversation and asked him lots of questions about himself but this was not reciprocated. The bulk of the date seemed to be focused on him. When the go-between asked me how the date had gone and if I would go on another one I did not know how to respond. I did not want to break my general rule and he seemed like a fine boy, but, on the other hand, I felt a little hurt by the lack of attention he showed me. I wondered why he was even going out with me if he was not really interested in me. I still have not answered and I’m unsure what to do.

Thanks for your help,

Second Shot or Not

Dear Second Shot or Not,

I am sorry you did not have the greatest experience on your date. I know that generally people go on a second date to be polite despite how the first date may have gone. This is a kind rule, because if the roles were reversed and you were having an “off” night you would not want to be judged so quickly on a first date. It is possible that this boy was simply nervous and unable to fully give his attention to you; perhaps, seeking your approval, he went a little bit too far and wanted to make sure you had a full picture of what he was about. I understand, however, that this can definitely be off-putting.

If you sense that there was an arrogance about him and he simply wanted to talk about himself and was not interested in you, then there is no reason to try again. It is his loss and he should probably speak to someone about the proper way to conduct himself on dates (he can always contact me :). However, if you think that it is more likely that this came from a place of nervousness then perhaps it is worthwhile to give him a second chance, especially since you two seem to have so much in common. I think it is worth telling the go-between your concerns about dating him again and seeing what response you receive. It is definitely a worthwhile rule to give someone a second shot, unless you simply cannot imagine it going anywhere. Good luck!

Im yirtzeh Hashem by you,

Shoshy Goldstein

By 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.