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.