Most Helpful Guy
No guy would write a girl off for being "too bold or too desperate". If he says no, its because she is unattractive to him. Simple.
But if you are attractive to him, he'll be ecstatic, and have no reason to say no.
So yes, its a gamble. Now you know how guys have felt for the past few thousand years. I think its about fucking time girls have a taste of it themselves. (sorry getting a bit off topic 😅)