Subscription seems to me won't work well because the churn rate of such app will be quite high (folks will play few weeks and learn basic "quests").
Using data is very controversial as can be seen in comments - also not sure how to monetize it well.
put another way, what value does this have over a static html page of "150 cute date ideas" from Elle or Cosmo that I could just cut out and pull out of a hat?
searching for "cute date ideas" gets me to Marie Claire with "80 Fun date ideas for when you're tired of a Dinner and a Movie". And with the fashion mags, if I pay them money I get plenty of other stuff that's not date ideas, and won't datamine me (as hard)