I've encountered a bunch of weird glitches in Lilith's gift/hangout dialogs. In some cases it seems like it concatenates three different scenarios together at once - horror movie, dinner, and hang out - repeating the whole "You are closer to developing your relationship..." part 3 times. In one case on a Sunday night after this happened, it then played the sleep cutscene and displayed the "Your rent has increased by $250" and "It's Monday..." dialog 3 times as well (it did actually increase the rent by 3x). It then immediately jumped to the "Wanna sleep in my room tonight?" dialog with Lilith (not sure if that's intentional), and then outside her house in the morning.
On a different case (which happened multiple times), after playing all three hangout scenes like above, it cut to Lilith's dialog for unlocking a new outfit (gothic elf), then cut to her character card, and then got stuck in a loop where closing the card repeats the outfit dialog and the card pops up again indefinitely. (Going on a date through the card option was able to interrupt the loop).