The Jewish community is small. It's even smaller when you're dating. And it shrinks to minuscule proportions when you only take into account those who are seriously looking for their beshert and not the ones who are fishing for casual dates or hook-ups. Chances are the same people you see on J*Date you'll also see at a bar, working out at the gym or catching a concert at the park. If by chance you happen to run into someone you've never seen before, odds are they're the friend or relative of someone you've already dated... or your friend or relative has already dated them. The Jewish dating world can quickly become incestuous. There was this one guy I met on J*Date, Adam, whose family seems to have been intertwined with mine since the beginning of time. His dad graduated from high school with my mom, our uncles grew up as best friends and his grandfather was one of my teachers in sixth grade. I know it sounds cute, but it can get obnoxious. Case in point: I was recently set up with a guy I supposedly knew when I was little. My mom even pointed him out in pictures from my second birthday party. A charming story, sure, but it didn't equal fate. I met another guy, Ariel, at an organized happy hour for singles who recently moved to town. After adding him as a friend on Facebook, I found that he knew many of my elementary school classmates and was able to utilize the six degrees of Jewish separation and do a quick, undercover background check. All of our mutual friends heaped praise on him and gave their blessings. Although he isn't my beshert, I can now count him as one of my good friends, all thanks to the endorsements. A few years ago, I met Eyal at a networking event. We quickly discovered that his best friend and my sister had dated in college, but it wasn't until we played Jewish Geography a few months later that we figured out I had dated his sister's best friend's brother. It may sound like a distant enough connection, but four degrees of separation was apparently enough to skew his view of me. In Eyal's mind, the kind of woman who would date his sister's best friend's brother isn't the same type of woman Eyal would date. Which brings me to a topic many women spend time fretting over: due to the seemingly small circle of Jewish singles, is it okay to date an ex-boyfriend's friend or a friend's ex-boyfriend? That all depends on how serious the relationship was, why the relationship ended, how much time has passed, and how strong the friendship is. In my opinion, a relationship that lasted more than six months, a friendship that is more than five years old, a relationship that ended less than two years ago and a break-up that was overly dramatic all equal too much history to make it permissible. But in this world of casual dating, there will probably be plenty of times when it is okay. Think about how many acquaintances you have, now think about how many of them have gone out on a few dates with someone only to realize there was no chemistry. I say, all those dates are fair game! When I meet a guy who has dated a friend of mine, I want to make sure it's okay with her, but I don't want to know the details. Just because he acted one way with her doesn't mean he's going to be the same way with me. Hopefully, he learned from that relationship and her loss is my gain. All's fair in love and war, right? Many successful relationships are the result of shidduchim, the ultimate in Jewish Geography. Shidduchim don't always work out, no matter how good the intentions are. Halfway through a recent blind date, I realized the guy would be perfect for my friend Julie. I got really excited at the idea of making a match, but setting up a guy whom I myself had met on a shidduch wasn't going to be so easy. Shidduch shuffling is not a sport. Even though I thought he was a quality guy, passing him off to my friend - as amazing as she is - is still rejection. I tried as hard as I could to soften the blow, but he has yet to call her. For the most part, Jewish geography can be helpful. You know what kind of company he keeps, who his friends are and if he's an all-around good guy. But it can also ruin a perfectly good prospect. Sometimes it's better not to know those details, especially from a secondhand source, because that may not reflect who he is now or who he is around you. And really, that's all that matters.