This is my guess so take it with the tiniest grain of salt
Assad: He started to be interested in her because of what he heard her over say while pretending to be asleep. Many talk shit about him behind his back but she while she thought he was asleep not only did she say she liked him but also wished for him to be happy.
Yeah honestly the story is a bit- well kinda bad when it comes to their relationships x_x it's like Assad is like "oh wait you don't like me anymore? That can't be right I'll do things for you and make you like me again" and it's just odd! If this woman forced me into this relationship and then she said let's annual the engagement I would be so happy like- it just doesn't make much sense to me tbh
Nope she said all that when she first meet him and thought he was asleep. Then they have the conversation about breaking up. I agree that he should just let go but it kind of a staple of these types of story, heroine isn't into the lead so they let them go but in a way that shows them affection that they have never had. ML is now interested and wont let go. FL falls for ML. Hijinks/misunderstanding/drama ensues. ML and FL get together and live happily ever after.
I think this is one of those "you used to love me and I didn't give a shit about you but now ha you've moved on, I love you" kind of cliché which isn't the most unrealistic things ever. I know a lot of people in real life who only feel attached to someone after they decide to move away or get a new boyfriend/girlfriend. It's human nature in a way and it validates he "you only know the true value of something after losing it" kind of thing
I find it so weird that he likes her .-. like with Cion I can understand since she is all he knows and I feel like Jay is the type that doesn't like losing but Assad? (Sorry If I spelt it wrong) is just weird? Idk but both Jay and Assad confuse the hell out of me as to why they like her x-x especially since she's treated those two the worst