Hey Mark!
Thanks for the movie tip. I'll be sure to watch it some time!
As for your more general question: I think it could be any challenge, but I also think that the "make this person want to be in a romantic relationship"-challenge can ever be fully completed.
I don't believe that, once you've "conquered" someone's heart, you can then take that persons's relationship with you for granted. All relationships have an upkeep of some sort. Fail to live up to the upkeep and the relationship falls apart. So, in a way, I guess you'd have to "conquer" that person time and again. Prove to him/her that you're still worthy of being in that relationship. Same goes for friendships, family, colleagues... or at least, that's how I see things.
Btw. I also think that "loving someone" (as a spouse, friend, brother, etc.) is different from "being in a relationship" with someone. I.e. the love I have for my friends is unconditional, but my relationship with them requires effort from both sides. If a friend fails to live up to his/her part of the upkeep, I wil not love that friend any less, but I will probably choose to lower or even abandon my upkeep on that relationship...
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