I love senpai's growth, at the beginning of the series he would have given up after realizing he us not cool and handsome, now he have the courage to act. I also love how Nagatoro was so enthusiastically on board with the idea when she realized what was happening. This is exactly what he needs to build up courage and self confidence.
For the career path, I guess senpai will be convinced by Nagatoro to aim for something he loves and try to maybe becoming a painter or a mangaka. Nagatoro will probably choose to become a pro swimmer and then take English lessons....wait, I think I'm mixing things up.