@givemersspls
"There's no way to tell what Sang-Won could be thinking."
Pretty sure that is what she was coercing her to do. I think the conversation boiled down to:
Do you have feelings? Let's check. Yes you do. Now go act on them.
"But Grandma what if he doesn't like me"
Well you can never know that just thinking about it... so what do you think the next logical step is now champ?
"Also, the entirety of her speech on how meeting other people isn't a calculated thing. Hmm. Who is a kind of crappy parent who has manipulated basically all the main characters?"
I don't think the calculated element she was referencing was the one you are thinking of. She isn't talking about their meeting beeing calculated but what I think what was implied is that it is never really calculated who you are going to fall in love or bond with. For example, I worked as a door to door salesmen at one point. Even though my routes were preordained, the types of people I met were completely random. Some were the kindest people on the planet and others wanted me to die because I was a solicitor. One of the nice ones is my friend to this day. Even at first when I was smoozing him up to sell him a package or personalities didn't click very well. Still to this day we are quite the mismatched pair on just about everything but he is still my bro.
For the record. I quit within the week because I was told we would be going to places who do not have a soliciting ban. I felt like a total jackass but I needed the job. I got a new one the week after though so it all turned out OK.