Dawww my internet bro all grown up
Don't I have a say in this? It's customary for us to talk about shit like that over booze you know.
In all seriousness, go for it. I tend to become timid and awkward a bit myself, but if you click with that person, you'd be surprised how natural and organic it becomes. And you'd be surprised at how much you wouldn't care about judgment because you know she wouldn't judge you.
For instance, I never act silly or dumb around people, and I can tolerate people hating me (heck I can even enjoy it), but the one thing I cannot abide by is having my intelligence insulted. But with special people (a very rare experience I've had), I act around them like the silliest dumbest fool, because I stop worrying about my image.
Oh also, one sure thing for me that makes you know you made it: comfortable silences.
There is nothing more awkward than silences in a couple or mutual LIs let's call them. Except if you click so much that both of you know that you don't have to talk nonstop all the time and are perfectly capable of being silent for 15 minutes or half an hour or even hours, doing nothing but staring, or eating or whatever. So if you do end up meeting and have comfortable silences, consider yourself up a level.