
Me: ok Jiwoon you have two dialogue options here to talk with DG, you can choose the WORST POSSIBLE REALLY HORRIBLE one, or you can say something nice. What do you choose?
Jiwoon:
Me:
Jiwoon: hmm this is hard
Me:
Jiwoon:
Me: c'mon it's an obvious choice!
Jiwoon: ok
Me:
Jiwoon: I choose the worst possible really horrible thing to say!
Me: NO!

A simple suggestion like that worked the last time so why not just suggest it again?
Besides Jiwon is confused and he most likely doesn't love DG.So his reaction is totally understandable.Give him a break lol.
I actually appreciated that because it shows that Jiwon is human and not just an asshole like people often call him here.
If he was an asshole he would had easily lied to DG and respond to him right away and tell him that he loves him like DG wanted to hear and that way Jiwon could have DG back but he chose not to.
Besides DG was very aggressive and didn't give Jiwon enough space to clear his thoughts and talk things through so that made Jiwon nervous.
DG just wanted a quick answer but that's not how such serious matters work out...

Exactly because DG seemed to be over him. Jiwoon knew all along about DG's feelings and he also knew that was the only reason why he accepted them being sex friends to begin with. DG is a romantic boy, as he said himself, and he doesn't like loveless relationships. By asking DG to put himself in that position ~again~, now with the plus that DG knows Jiwoon will never love him back and treat him well (or so he believes), is akin to asking "last time you let me cut out one of your fingers, why not let me cut out another one?"

I don't believe Jiwon "knew that DG loved him from the start" because as we have seen Jieon unfortunately has never received love in his life therefore he doesn't understand it.
I think that Jiwon only said that he knew things would end up like this from the start was just the normal human reaction most people have.
Blaming ourselves for something that went wrong.
It doesn't mean that he knew DG "loves" him.
Also there is this issue that Jiwon has.He thinks that only his persona "Alex" matters and that's all he has to offer.And Jiwon knows that DG "loves" Alex only.
DG got with him for Alex and for a long time Alex was the only one DG could see except from the time Jiwon got drunk.
So in conclusion it's complicated.
This I so unbearably cute I feel PERSONALLY ATTACKED by all this fluffy