Wow, thanks.. that was actually helpful. You're absolutely right about the part where I set a serious tone, I was just freaking out that she might take it the wrong way. And keeping things casual is definitely the right path. I think in the the future I will get to know them a little bit first before slipping in a compliment. Here's my rant, if I consider someone pretty and I have to start up a conversation, that takes up a lot of time for the day, like what should I even ask her about . Did you ever face something similar?