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I’ve gone out with guys of various hashkafas, and I haven’t noticed any differences. In all cases, they might ask either of us first or both simultaneously. But again, I am talking about American singles in Israel which may be its own thing. And when I say various hashkafas, I guess most were somewhere in the grey range at least in terms of background.
On SYAS, they let the girls choose if: 1. they want to be asked first 2. they want the guy asked first or 3. they want both to be asked together. I think there might also be a choice 4. I don’t care.
I was talking about before the first date. After each date, I’m still not sure what people expect. I think some people expect the girl to answer before the guy does.
I always assumed the shadchan was supposed to get back to me and tell me what the guy said (either way). When they don’t get back to me, I always assumed that meant the guy said no. But once when a married friend set me up and she didn’t get back to me, the next time I saw her she asked me why I hadn’t called her. I told her that I assumed the guy said no since she didn’t call me. She said she was waiting for me to call her. I didn’t get that – why didn’t she just call me? And the whole thing made no sense to me – if the guy said yes, she should have called me, and if he said no, why did she care if I called her or not?
Another time (before the first story), my teacher’s wife set me up. I wanted to go out again but was waiting for her to call me (because I thought that’s what I was supposed to do). Sure enough, she called me afterwards (I don’t think it was the next day, but shortly afterwards), but it turned out she was calling to invite me for Shabbos, and she didn’t say anything about the shidduch! So I assumed the guy wasn’t interested and she was uncomfortable telling me.
But then after the first story happened (which really happened second), I thought maybe my teacher’s wife was also waiting for me to call her. But I still think that if the guy had said yes, she would have called me.