1. Yes, guys are oblivious, and for the majority of guys, they struggle to be the first to reach out, especially when you are already friends or acquaintances. Even with random girls most guys fold. And yes the chase is so much fun, like oml flirting is so fun if done right, but you can be forward and still have the fun of the chase. 2. That’s too unspecific to tell, would vary by person.