Darrell Bock has recommended the four volume set written by Michael Brown on Answering Jewish Objections to Jesus as “a wonderful resource for study of the relationship between Christianity and Judaism.” I personally own the first three volumes of this set and I gladly add my recommendation to his.
Many of the questions that Jewish people have about Jesus are very different than those one will confront in the academy or the broader marketplace of ideas. In these four volumes Brown deals with (1) General and Historical Objections, (2) Theological Objections, (3) Messianic Prophecy Objections, and (4) New Testament Objections.
You are looking at close to $100 to buy all four volumes in new condition, so you probably don’t want to run right out and buy them unless you have an immediate apologetic, evangelistic, or academic need. However, it is good to know they exist and that they are a good equipping tool so that you can keep an eye out for discounted copies of them. [I was able to pick up my three volumes at a discounted price ($3.98 each) several years ago. And, they are available on Kindle for about $13.00 each.]
If you want to start with just one volume, my favorite is volume 2 on Theological Objections. In it Michael Brown works through 28 unique questions using the Hebrew Bible, rabbinic texts, and the New Testament. He covers topics such as the sacrificial system, atonement, the Trinity, the Law, and the Messiah. This is not the kind of book that one can enjoy if read passively. However, inquiring students of the Bible will be rewarded for the investment of mental energy necessary to work through the nuances of the questions and answers and will find engagement of the material to be both stimulating and challenging.