He can't say yes unless I ask?

He can't say 'yes' unless I ask.
But then again, he can't say 'no' either.
This seems all too familiar.
Last time didn't work out so great.
Which is worse, rejection or regret?
I don't want to live in fear because of something that happened in the past.
Maybe I should just go for it.
Like pulling off a bandaid. (Did I really just compare this to pulling off a bandaid? haha)
The anticipation's the worst part.
Good things have come from taking risks in the past :)