So I've noticed that a couple girls I know have been strangely receptive to compliments accidentally (where I didn't intend or expect for them to be taken that way). This seems took me by surprise for some reason, as if I've completely forgot about them as a tool. And it makes me think back to examples of guys who just hit on women on the internet or over text and over time basically drive the girl wild and make her want to fuck them. At least how I've seen it.

So my questions are: How much is too much flirting or complimenting over text with random girls you're in contact with? Is there such a thing? I just told a girl that she looked great at edc with her outfits, would it be creepy if I got specific and stated which one? It seems like pickup is just a game of whoever can flirt the most and make the girl like you.

But on the other hand, I have experiences with a gay guy almost grilling me (I'm friendly with them, but not really gay or bi) to the point where I'm frustrated or angry that he wouldn't leave me alone. So I don't want to be that.

Like the guys who talk about all the nasty things that they want to do to a girl, some girls dig it and then are disappointed if they don't perform like they said they would. Is that obscene or.... viable? Time and a place?