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So much to answer…
Why does he want to be Ashkenazi? I have no idea. He comes from a very proud Sefardi family with a history of great rabbeim in the “old country.” I think he was influenced early on to think that if he’s going to be a great Rosh Yeshiva and be taken seriously, he has to be Ashkenazi. While his family speaks Farsi, he learned Yiddish.
Did the girl settle? I don’t know. He is VERY outgoing and talkative. A very friendly guy who will talk to anyone. But I’m told that when she talked to the boy’s mother she was friendly and wanted to know more about her son. So I think there’s some genuine interest.
They’re Americans dating in the Israeli culture. I don’t know how much that plays into the awkwardness. I know that when I was in yeshiva and the guys were dating, if the couple wasn’t talking after 3 dates, it usually ended, but could continue for a few more if it’s a good match on paper.
How does he know that they share similar goals and values? It’s all on paper. How much of that stuff is sincere, one never knows.
We’re going to meet the girl in a few weeks and actually see them together. I think we successfuly manipulated them into a double date.