How do you understand this sentence? "もうそろそろ何度目かの正直的な感じでしょ！！”

Question

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:

もうそろそろ何度目かの正直的な感じでしょ！！

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?

Answer 1

As the comment says, this is a deformed version of the common idiom 三度目の正直 "third time lucky". It's common to "hide" a part of a well-known long cliché/proverb using なんとやら, etc (see this). By not saying everything, you can convey a you-know-what-I-mean sort of sentiment. This 的な is just -ish or -like, but it is applied to 何度目かの正直 as a whole.