Like many things in life much of this is comfort and confidence. If you don't like single handling or lack the confidence in you and your boats ability it will be hard. This is not a knock on anyone's ability or skills but a reality we face in all life.
Now, as we become more confident in our skills and comfortable with our boat we will begin to gain the skills and confidence to single handle things. When I first started sailing 20 years ago on small keel boats the thought of single handling a 41' ketch would have never crossed my mind. Now some 20+ years, later I am preparing to possibly sail single handed from San Francisco to LA. I'll take all the right precautions and be prepared but otherwise it's just a long day sail (ok several days) sailing
You mentioned that you just finished up your classes, you now have the basics, and will learn lots everytimeyou go out. So will your friend. Will he ever change his mind? Who know's, if he keeps sailing and always has crew maybe he won't need to. Either way, enjoy, learn and sail on, sailing is almost never about the destination but always about the journey.
Fair winds,
Capt. Vic