We recently got a new female analyst. We invite her for lunch and sometimes have small talk. Thing is, there's literally zero chemistry. We can't include here in our dumb Skype chat because its usually filled with incredibly dumb offensive memes - so we just try to keep our laughs down. We tried invite her to video game night and even organized board games just because she wasn't into video games that much. But again, there just isn't any chemistry. I genuinely think that the border isn't just between anti-social/pro-social. I also wouldn't ever consider making deprecating jokes towards her. What's considered inappropriate is too blurred also. I can make fat jokes/racist jokes/generally inappropriate jokes with most guys, since we know there's no malevolent intent. It's kinda cathartic and it's a two-way street. I genuinely don't think I can be like that with any woman in the workplace. I know comedians can have such a relationship though, so maybe there is a chance? Maybe not now when people are publicly executed for speaking their mind but in the future.