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I once pushed myself to go out more than once with someone b/c he fit the bill, but I was NOT attracted to him. I continued for quite a while, and the guy really thought things were progressing. My feelings about the lack of attraction pretty much stayed the same, and I eventually ended that. I think it’s very rare that someone with whom you’ve had little or no attraction for, that it can work. Sometimes it can grow (depending upon how neutral the feeling was. A person’s appearance can change with something as simple as a change of clothing and or opening up personality wise. But, from experience, if it doesn’t grow within the first few dates, it probably won’t. I know of only one girl who married a man she was not attracted to (chemistry means either physical appearance or personality or both). She is still married to him after many years. But a) she followed the advice of her rav to marry him and b) she was truly not a shallow girl. She dressed neat and clean, but gave very little thought to her appearance. The friends she chose baalas midos tovos, not the super popular outgoing types who everyone flocks to. So she always chose based on good values.