Take 9 south to I-69 south, stay on that for about 30-40 mins, you'll come to a town called Indianapolis. You should not have a problem finding something to do there. Walking the canal is always a good date activity, free and a great spot to get to know eachother, plus it may be cooler out so you can be nice and offer your jacket or hold her close to keep her warm.
As much as Anderson is turning into a ghost town, there's still some stuff there. The casino, of course, then (I think it's on the same road) there's an old fashioned drivein where you can get good stuff to eat right in your car. Mounds park, then a few minutes to Pendleton there's another park there, and a thing or two in town. See if the Wright Brothers are playing up there; they put on a nice show in one of the parks. Over to Muncie there are a few things, as they need to keep the college students amused. There's a radio controlled airplane museum and facility around there somewhere. XGF could tell you more, but I don't talk to her anymore.
Yeah, on second thought, at the casino, you're not really "together", you're just in the same place, with a lot of sensory overload. More of a thing for an established relationship.