The context is about character(1) doubting character(2) whether or not she can kiss the main character because character(2) couldn't express her feelings to the main character, so character(2) said:
I interpreted it as:
Surely it is a honest feeling for the umpteenth time!
I shortly gave up and checked the English translation which says
It's sure to go well by now, you know!
I'm not sure I understand what 何度目か means but I found this link: How should I understand 何回目か in this sentence?
I'm also pretty confused at 正直的, if 正直 were to be understood as "honest" why is 的 used?