Thanks for the Lani info, it sounds like this is event is later than I expected it, the guide I was following made it seem much sooner:
Raise Stats
Beat Lani (Sparring)
See her scene
Join Guild and go on a mission
Ask Lani to join party
Take Lani to Guild
Beat Lani (Sparring)
See her scene (Massage)
There's a note on that last tip that reads "Special scene if you ask for a date, then see them in Marla’s Room the next evening (Before the date happens)"
I downloaded this guide from Lewdzone IIRC.
Also, re: Challenger, it seems the only way to get the top rank is to raise stats as much as possible before doing any fights (i.e before chicken fight) and then go straight to the 4-star dungeon and rely on Light magic skills to beat mobs, I will try this on my next life.
Any tips on raising Magic Proficiency? I edited my original comment so you may not have seen that question.