I don't go to Montana's often, as they don't really cater to any of my particular cravings. The food here is ok, more than anything. They serve a small assortment of burgers, pastas, chicken dishes, etc - a general hodgepodge of meals that you could find the equivalent to at a handful of other restaurants for about the same price. I'm never particularly wowed by anything on the menu; there isn't anything that makes me think "I have to try that!", but generally what we do order is tasty and satisfying at the time. I do recommend the Honey Apple Cobbler (om nom nom).
The thing I love about Montana's is the paper tablecloths and mug of crayons available at every booth and table. What can I say - I'm a sucker for gimmicks and anything that gives me an excuse to color on random surfaces. While this doesn't really lend to a classy dinner date (whatever, you're at Montana's), it is a fun sort of distraction, giggling as you try to determine if your companion has drawn a lima bean or an airship.