Paulie said something about fixing rocky up with his first woman and rocky said she was pregnant and Paulie said so what you was no prize either. What does that whole convo mean? Was rock there for somebody who was pregnant?
I think that Paulie was trying to take credit for Rocky's first serious relationship with a girl. That girl being Paulie's sister, Adrian. Paulie had approved Rocky to date his sister, and so he felt that Rocky owed him. But Rocky's relationship with Adrian turned serious because she became pregnant, and not because of any further involvement by Paulie.
Paulie then insults Rocky by saying that he wasn't a prize either, meaning that he didn't consider Rocky to be much of a catch with girls in general. So, Paulie still felt that he was owed for Rocky ending up in a relationship.