Don't worry. Gina's logic is definitely there, but it may be an acquired taste. 😉
Luckily, we have just a function for helping out ingame already. Once you click D.G., you enter the assisted mode:
In this mode, the hold it and objection buttons are highlighted if you need to use them on this line of dialogue...
...and if you hover the items, the correct one is also highlighted with a red border.
So, in summary: Use Hold it on every line, and hit objection when the button turns red. You should be able to clear the trial like this and get Gina to Lvl6 afterwards.