In closing, let me encourage you not to get side-tracked or intimidated by such an approach to Messianic prophecy. Keep alert and learn to spot an unbalanced focus on Second Coming prophecies.
If your Jewish friend rejects the Messiahship of Jesus on the basis of Second Coming prophecy, tell him that he's ignoring a whole body of Messianic material. Tell him that he's bypassing the predictions of a suffering, rejected, and humble Messiah. Then take your friend to Zechariah 9:9-10 and to the Gospels. Show your friend how Yeshua fulfilled Zechariah 9:9 during the Triumphal Entry.
Then go on and show your friend that Jesus is also portrayed in the Passover lamb. Show him Exodus 12:1-6, take him to I Corinthians 5:6-7. Show your Jewish friend how Jesus was the perfect spotless Lamb of God during the Triumphal Entry as well.
Then let the Word of God do its job in your Jewish friend's heart.