Meaning of のs in this sentence


The below sentence is inner thoughts produced by the guy going out with a hot
girl (from manga). I get a general idea but I am not sure about its grammar.

> 俺みたいな **の** に、付き合ってる **の** 、なんて時間の無駄くらいに思ってて、当然なのに...

I wonder if the first の is a normalizer for 人. Also, I am not sure about the
particle に with the verb 付き合う. It is supposed to be と.

What is the second の is doing? I think it is redundant because of なんて?

Maybe I am parsing the whole sentence wrong. There are two のにs in this
sentence meaning although. The second の is normalizer and なんて means something
like なんといっても.

> 俺みたいなのに... 付き合ってるのはなんて時間の無駄くらいに思ってて当然なのに...

But I am still not sure about 俺みたいなのに. Why it can't be 俺なのに.




  * A **と** 付き合う and A **に** 付き合う are both valid expressions. A **と** 付き合う tends to mean "to date A" (A and the subject are in a romantic relationship). On the other hand, A **に** 付き合う does not assume a romantic relationship, and it's often more natural to translate it like "to keep A company", "to go out with A (for a practical purpose)", "to spend time with A", "to socialize with A" or even "to play along with A".
  * The first の after 俺みたいな is a substitute for 人. There is no のに meaning "although" at this position.
  * The second の after 付き合ってる is a nominalizer that turns 付き合う into a noun. なんて can take both a verb and a noun, so this の is optional, but this の doesn't feel redundant to me.
  * 俺なのに ("although it is me") makes no sense here.

> 俺みたいなのに付き合ってるのなんて時間の無駄(だ)くらいに思ってて当然なのに...
>
> It's only natural if she thinks it's a waste of time to socialize with a
> person like me, but...




  * A **と** 付き合う and A **に** 付き合う are both valid expressions. A **と** 付き合う tends to mean "to date A" (A and the subject are in a romantic relationship). On the other hand, A **に** 付き合う does not assume a romantic relationship, and it's often more natural to translate it like "to keep A company", "to go out with A (for a practical purpose)", "to spend time with A", "to socialize with A" or even "to play along with A".
  * The first の after 俺みたいな is a substitute for 人. There is no のに meaning "although" at this position.
  * The second の after 付き合ってる is a nominalizer that turns 付き合う into a noun. なんて can take both a verb and a noun, so this の is optional, but this の doesn't feel redundant to me.
  * 俺なのに ("although it is me") makes no sense here.

> 俺みたいなのに付き合ってるのなんて時間の無駄(だ)くらいに思ってて当然なのに...
>
> It's only natural if she thinks it's a waste of time to socialize with a
> person like me, but...

