As far as I know, you're right with your observation.
2.
Do you ever fall in love? --> It might be said by someone who's desperately in love to someone who doesn't have the same feelings: "Look, I've tried to do everything I could but your feelings haven't changed a bit. You're cold, your heart is a stone. Do you ever fall in lov
I don't think this means dating in this context. That's more like going out together.
It's closer to your 2nd interpretation, but the sentence is a bit confusing, esp that repetition of both. Do you have a full context or this is something invented by yourself?