Hey there College Kid!
In my opinion, you need to go back a little in your debate with your friend.
First, you need to agree upon the issue of authority. In all my dialogue with Protestant friends, I have learned to always start at this point, and not go any further until this has been established.
Until you have authority sorted out, you will just be exchanging verse for verse with this person. It will just be their opinion against yours (or the Church’s hopefully

) until the cows come home.
I am in the beginning stages of dialogue with 2 very knowledgeable Protestants right now, and I have made the point at the outset that we will not go into any other area of discussion until we have exhausted the issue of authority.
This has been well received and agreed upon.
I can’t see any point of discussion on anything else, except perhaps Faith Alone, until you both agree on who is the rightful interpreter of any verse of the Bible.
I hope this helps you out. I think you will find your friend will agree to start back at this point too.
I once spent 90 mins on the phone with a Protestant friend going around in circles through all the usual objections e.g. Baptism, Purgatory, Indulgences, Confession etc, because there was no final authority that we had as common ground. The conversation went nowhere.
May God bless you and your efforts.