Back in September I went out with a guy (let's call him "Bob"). He was an investment banker, nice, cute and a little dorky and had a really high pitched voice. We revealed all the typical information people reveal on a first date and that's when I learned that he came from a very religious (Jewish) family who resided in a very religious neighborhood. The same neighborhood in which my boss lives, actually. Not really making anything of the situation, I enjoyed our date, but wasn't super into him. After two glasses of wine I said that I should get going. He offered to walk me home because he was a gentleman, not a creeper. I declined his offer, but agreed to walk with him halfway (since I knew he had to go in the opposite direction at that point anyway). It was there, by the second aveneue construction site, that my short, high pitched, religious date tried to kiss me. Shocked by his brazenness, I went along with it for about three seconds and then darted out of there.
The next day when I got to work, I told "Chelsea" about my date the night before and about how his family lives in the same town as Boss Man. Chelsea instantly stated "Oh, well then he knows the family." I said, just because they're religious and live in the same town, doesn't mean they all know each other. So, we did what any employee at a normal firm would do, we paged Boss Man and asked if he knew the ---------- Family. Boss Man's response: "Yeah, I pray with his father."
Chelsea then proceeded to tell our boss about how I went on a date with "Bob" and about how "Bob" tried to kiss me and that he had asked me out again. My boss is a very nice man so he didn't want to say out loud what his facial expressions were clearly stating - he was mortified that the son of this strict family was running amok dating gentiles in the City. My boss gave me a look like "you need to put the kabosh on this ASAP." So being the good employee that I am, I agreed to go out with Bob again.
We actually went out two more times and I tried to figure out if he liked me or if he was secretly planning some grand rebellion against his religious family and needed me for it. I asked him if his parents mind that he's not as religious as they are and he said that they didn't really mind as long as he didn't "flaunt it in front of them." I began to wonder then, how would he ever introduce me to them? Would he invite me to Shabbat dinner at his parents' house and hope that I wouldn't tell them that I am a gentile? Would he be worried that I would act totally obnoxious and show up wearing a giant cross like rappers wear or that I would insist that we say grace before eating? Or that I would ask for a side of dairy product with my meat? Would my boss be there? Would he be really angry with me for not listening? There were way too many concerns.
I wasn't even all that into Bob, but I went out with those two other times because he was nice and it made for great conversation with Chelsea and my boss. After the third date though, I made up a lie that I was going to be really busy in the coming weeks. I think he got the hint because he didn't contact me too much after that. Sometimes when I'm talking to my boss about a case of mine, I ask him how "Bob's" family is doing and remind him about how funny it was that I went out three times with "Bob." My boss laughs, but deep down I know he is happy and proud of me for not causing problems in his community.