Possibly, Bacchus, but here's my reasoning on this.
I'm of the viewpoint that Jill is, as demonstrated so far...a REAL woman. ALL the other women in the game are broken somehow (cheaters, sluts, prostitutes, irresponsible, criminals, drug addicts, self destructive, insecure, selfish, manipulative, or just morally bankrupt). She is the ONE character who is grounded, confident, uncompromising, and...according to her...monogamous. She made it very clear about how she feels about more than one partner in a relationship at the start of the Tennis Date. I don't think she has the moral "fluidity" to form a relationship with multiple partners, particularly after she made it clear how she feels on the subject...Despicable!
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Sorry to shock everyone, but the vast majority of our species is monogamous. There are some who aren't but those are rare. Don't believe me? Cheat on your wife or girlfriend or find out she cheated on you and come back and tell us how it went. It's one of the worst things one human can emotionally do to another. Multi-partner relationships are truly rare outside of books, games, movies, etc, and don't actually work or even make sense in the healthy human heart. If Doc follows along with founded reality and the human condition, Josy/Maya/MC three-way path, is doomed. And they would all suffer...sadly, Maya will likely take the brunt of the pain IMHO. Of course, Doc won't do that to the characters, nor should he in the story. It's a story, and we will want closure before the end.
In reality, most of the time these "open" relationships leave behind wounded and shattered people. For more information about how that plays out, please review the MC/Josy/Maya storyline, paying particular attention to the opening scene of when MC chooses to stay with Bella (where we see not only the depth of the MC's pain (this beautifully written scene still chokes me up..."Please. A little while longer...."), but also we see Bella's rather blunt viewpoint that the whole multi-partner idea is "stupid.") Hehe...Doc covered ALL this stuff in the game!.
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I do not think that Jill is that kind of a person to do what Josy, Maya, and (lest we forget) the MC did to each including the (plausible in fantasy only) three-way option they are going to "figure out". I am just friends with them in my Main Save...I chose to path of "they chose their path, now they have to walk it as I walk mine." They have each other to comfort them...they don't need the MC anymore.
As demonstrated by Jill's character so far she isn't that person, unless she experiences a dramatic personality change (which would be sloppy writing), or Doc just caters to Fan Service (and the Harem mentality most of us have in this genre of game. Who among us have played through the game at least initially trying to hook up with AS MANY GIRLS POSSIBLE in a single Save? Hehe...). In fact, if the MC wants Jill, she will expect him to have no one else. If he does, he'll lose something precious. The MC is a huge Man-Whore, so that will be a hard decision for him to make. Do I want The Prize, or to Sow my Royal Oats?
From a writing perspective, it's unlikely that Doc will attempt ANOTHER three-way relationship thing in the same game twice. He already did it in Acting Lessons, AND in this game with Josy,Maya,MC. It would be sloppy to do it again. You'll notice that every major character and circumstance are unique in this game so far. I don't think Doc would "Cliché" himself. I know many fans want to play a three-way with Bella & Jill but according to the characters and the writer...there is no foundation for that.
So, Jill as part of a Harem? Jill in a multi-partner relationship? Bella even?
Nah...Ballerina Chad is more plausible.