Just discovered this thread so I though I’d share my worst and best dating stories:
The worst was that a co-worker had a friend from out of town he thought might be a match. She was visiting friends in NJ for Shabat (I live in the Bronx) so he suggesed we meet after Shabat. I called her up and suggested several restaurants in Manhattan, all of which she vetoed because they weren’t certified by the local kashrut vaad. My attempts to explain that Manhattan didn’t *have* a local kashrut vaad fell on deaf ears.
So we agreed to meet at a hotel lobby in New Jersey. I warned her that it might take some time for me to drive there because of the likelihood of traffic over the George Washington Bridge. Well, there was no traffic on the bridge so I arrived 40 minutes early! And when I arrived I discovered that the hotel was hosting the annual banquet of the Palestinian-American Solidarity Committee!!! Here I was, cooling my heels in my yarmulke, surrounded by hundreds of Palestinian activists. And my date was almost an hour late. When she finally arrived she apologized but started telling me about the great right wing talk show host she had been listening to on the way. As anyone who is a regular reader of the comment forums here might guess, I would not find myself in agreement with right wing talk show hosts. The date sort of went downhill from there. That was my first and last hotel lobby date.
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About a year later a different woman from out of town contacted me on frumster.com. She had been attracted by exactly the honest stuff that shadchanim had told me not to tell any prospective partner. We corresponded by email, snail mail, and phone for five weeks before finally meeting. Before meeting, she talked with my rav, and I talked with two of her rabbis. By this point we were certain we were compatible; we just weren’t sure whether there would be chemistry. Her hashkafa is a bit to my right and her politics are a bit to my left, but our differences were not so great as to be incompatible. Well when we finally met we hit it off instantly (fortunately one of her rabbis had given each of us the shomer negiah lecture before we met in person!) and we were engaged the second time we met in person. We were married three months later and are still married 5 1/2 years later. 🙂 We are frumster match #152.