Hey Smooth, I was in Terre Haute on Sat. and dined at the Olive Garden. I agree with your restaurant choices. I really enjoy the Stables.
JTM, If you are up for a trip to Indy you can't go wrong with a trip to the Zoo then visit the White River Gardens which is adjacent and included in the price of entrance to the Zoo. Aside from the the Gardens, the big draw there is the Butterfly Exhibit. They have hundreds if not thousands of different varieties of Butterflies throughout a two level glass structure filled with tropical plants and water features. My wife is quite a fan of the place. Then you can top it off with dinner downtown (5 minute drive) at a restaurant of your choice. My favorites would either be P.F. Changs or Fogo De Chao (a newer Brazilian steakhouse).
Victory Field (home of the Indianapolis Indians) is also in between the zoo and downtown. Even if you aren't a baseball fan it is just a great time people watching and soaking up the ambience.
If your anniversary is around Oct 11, you can always get tickets for the So You Think You Can Dance Tour. Yes, it's at Conseco on that day and I don't want to talk about it anymore
If those options don't aren't appealing to you then fill us in on some of your joint interests and I will swing again.