Is your friend Catholic? Trad? Novus Ordo?
This is the first and most important question.
Novus Ordo
Tough sell.
This whole "two covenants" stuff is just Post-Vatican II Conciliar ecuмenism on steroids - it borders on being a denial of Christ Himself!
However, ask them basics, like "Do they think Jesus is God or just sent from God?" If they say "only sent from God" or that Our Blessed Savior only had a special relationship then I would be tempted to just say "Well, have a nice day." but let's hope it isn't the case.
I would spend a lot of time going over the first several sentences of the Gospel of St. John and ask them line by line how they read that. Since Jesus was with God and Jesus was God, why would a group of people who reject Him have a covenant that is still honored by the Creator?
You want to take the approach that the Old Covenant lead to the New and wouldn't necessarily need an "end" date. And that the Old Dispensation is strictly in preparation for the coming of the Lord and serves no other purpose, certainly not one for racial identity glorification.
Try to get them to understand that everything JP II or B XVI says isn't "handed down from Heaven" but don't overplay this or they may become defensive.
Ask them if Jesus is really God, why would He want a covenant other than His as non-revocable? (Is that a word???) Never to be revoked - for all time!
Ask them, philosophically, why they feel a need to defend a two-covenant system as if Jesus, Our Lord, said "No one comes to the Father except through me?" Why would the Creator of the Old Testament and the Torah say that?
Keep us posted on how your friend responds.