This is the central idea for one of the finest fantasy or science fiction shorts I've ever seen - Multiverse Dating for Beginners.
If I were to simply recount the story, it might seem familiar; a woman and a man walk and talk and are obviously interested in one another, and when the moment they share has come to an end, it starts over, but she knows what's happened, he does not. She explores the possibilities of the night through repetition, trying this, and trying that, but as the interactions continue, she begins looking just as hard at who she is, and who he could be, and that leads to an impressive degree of self-awareness, not to mention pathos.
This is a film where two characters, Ivy and Dave, go through a series of emotions, where each is so perfectly encapsulated in a moment. In a way, it is Ivy over-thinking at every turn, and Dave living in what always seems to be a moment of incredible promise. In that way, Ivy is the villain, but at the same time, in her eyes (and likely the eyes of anyone who hasever been in that moment where you're not the you you're sure you need to be to make a serious connection) she's desperately trying to NOT be the villain. To her, at least as time/space/universes go on, she is looking through the moment to the future, never quite connecting with the idea that all there is, all there can be, is the present.
Multiverse Dating for Beginners is a marvelous film, full of comedy, tragedy, and most of all, character work. These two are perfect at exploring. The direction and writing of Kelly Tatham is absolutely perfect, making the most of every nuance in a story that easily could have abandoned nuance for bombast. The way it was edited, and especially the titles, only makes the entire film feel like it is a unit moviing with full purpose towards a goal - to get the audience to realise that "There is only now... and maybe before."
You can see Multiverse Dating for Beginners as a part of the Something Funny series of shorts showing at Hammer Theatre SJ in Beautiful Downtown San Jose on Sat, Mar 3 11:15 AM, Sun, Mar 4 8:30 PM and Sun, Mar 11 10:15 AM, plus Century 20 Redwood City - Screen 10 Sat, Mar 3 9:30 PM and Sat, Mar 10 7:50 PM