I've spoken to a Jewish man who speaks original Aramaic about this passage and he laughed at how Calvinists interpret it. He said that those who understand the original language and the usage of the word "hate: in context with his elective choice would NEVER come to this conclusion. I agree with him for these reasons:
1. Paul begins the chapter expresses extraordinary love for his fellow countrymen who are being hardened in their rebellion, so unless you believe that Paul, writing under inspiration of the Spirit, is more loving than the God who is inspiring him then you can't come to that conclusion.
2. In the original language there are other examples of love/hate being representative of choosing one over another. i.e."...you must hate your mother and father..." Which clearly means you choose God OVER even your own parents, just as Jacob, and his posterity, were chosen OVER Esau, and his posterity, for the noble purpose of bringing redemption.
3. Even Paul refers to them being 'nations' in her womb prior to drawing this comparison, so it is not a stretch to understand his point from a corporate standpoint of using one nation for noble purposes and the other for common use, rather than the idea that God irresistibly saving one and not the other.
Oh yes, the Jews will correctly interpret Christian doctrine when we can't. How convenient to cite Jewish fables when one cannot answer sound exegesis.
The foremost authority of Judasim in the first centuries of Christianity is Jacob Neusner. He has written books in which he outlines his arguments against the doctrines of both Christ and Paul. I have them, and have read them. There is no mistaking what Paul was saying. I expect that if your Jewish friend were examined, I would find that he takes issue with Paul, not Calvinism
per se, and that he simply took the opportunity to bring Christ down further in your estimation. He must have gotten quite a buzz that one claiming to be a Christian minister has gone to him for enlightenment on a polarizing verse in the Christian Scriptures.
These national interpretations of yours are nothing new. It's the Jewish fable offered as the antithesis of the Christian preaching of the Suffering Servant of Isaiah. The Servant isn't Jesus, it's the Jewish nation.
Don't forget, the Jews believe Jesus was the illegitimate son of Mary, that He was a liar, that the works He did were by the power of Satan, that His disciples were and are heretics, that the letter you were asking him about is heretical, and that its author was justly executed for writing it.
Way to go, Scandal!