Hmmm I've done the other three so far, but I assume of these two choices;
2 of them are breakup variations:
a) if you rejected her for J&M or Sage(crossed out what I've already seen)
b) if you rejected her for Bella
going for Bella hurts Jill more?
If that is the case, I look forward to destroying Jill.
I thought it's predictable. It
always hurts her, since you have this bench scene anyway. She is still confused a lot, but, at least she doesn't feel betrayed. And their friendship doesn't seem to have been destroyed. Damaged, but not destroyed.
When you romance Jill and Bella at the same time, then it's the worst possible outcome, since Bella & Jill friendship gets ruined as well. During the bench scene you'll have an option to make things even worse than they was currently.
When Jill asks MC "Why you choosed her?" he may answer "I couldn't choose both of you". Then, she will try to kiss him.
If you kiss her back, then:
It gives you cheating points (+2) and the episode have an alternate ending scene with Jill. She doesn't cut MC polaroid photo if you did the thing above:
In any other scenarios (J&M, Sage or Bella w/o picking that particular answer choice in dialogue) she cuts MCs photo.
By romancing them together you're not destroying Jill. You're destroying Bella and her friendship with Jill. Bc if you played game with paying attention to details, Bella said several times that Jills friendship means a lot to her. She feels very guilty for what she did to her, and what's even worse, behind her back AND after she encouraged Jill to date MC especially. They have very different conversation in EP9 flashback in a scene where Bella comes to talk to Jill in preps mansion, depending on MCs relationship state with Jill.
You can play game for train wreck scenarios and patterns for maximum drama purpose or to get all possible outcomes and endings, but knowing DPC, you shouldn't expect any happy end from such gameplay style.
It's impossible to build happiness on someone else's grief, either in real life or in this game, at least in the long run. Karma is a bitch.