Of course Interstellar is just a movie so it is not scientifically accurate in all points. In your example I came up with 3 points:
1) Gravitational time dilation is real but for 2 hours on the planet/23 years for Romilly an object would have to be so close to a black hole that it would inevitably spiral into it.
2) The other problem is that the crew could not survive such high Gravity on this planet. (No matter how fit McConaughey is)
3) And the third that I can think of that even if they could, there is no chance that they could leave this planet. For a place with such a bit gravitational time dilation, you would need an escape velocity (How fast you have to go in order to escape the gravitational pull of a body) of almost the speed of light.
To try to answer your Question, Romilly would see the planet, her spaceship and all the past decisions that she made which led her to this place, get sucked into this super-massive black hole.