I finally played through most of this game and I was quite impressed. I'm definitely going to have to get episode 5 when it's released. I agree with Holy Bacchus that the interaction between the characters leaves a lot unstated and does feel very human.
On Josy in particular, I think the main issue is that she was isolated - both in that she was lonely, but also in that there was no one she could turn to for advice. She seems like the sort of person who needs to be around people, but she couldn't see Maya and her other friends had moved on. We also know that, like Maya, she didn't want to talk about being in a lesbian relationship.
I think she went on the first 'date' with the MC because she just wanted a friend to hang out with for a bit. After all, he'd been working with her for months and hadn't asked her out, so she probably thought he just wasn't interested in her romantically. It was only when she realized there WAS a mutual attraction between them that she panicked and called the whole thing off. That in turn made her feel even worse because on the one hand she felt like she had cheated on Maya, but on the other hand she enjoyed the companionship and felt like she had treated the MC badly.
From there it gets more speculative because we don't know what they said to each other or when they said it. But we do know they had started fighting and we know Josy told Maya about her plans to leave town, probably about the same time she told the MC. That's when the MC asked for (effectively) a second, and Josy said yes.
I suspect Josy wanted Maya to make more of an effort to see her, but Maya wasn't willing to risk it until she had a way out from her father's control. After her brief tryst with the MC, that became increasingly hard for Josy to take. So once it looked like she wasn't going to get in to B&R (thus might never see Maya again AND had no clear path out of her lousy situation), Josy started thinking about running away and making a new start somewhere else. When the MC heard that, he rushed back to see her. Maya didn't.
So when the date happens, it's no surprise Josy is really conflicted. As she said, she desperately wanted to feel loved, and here was the MC showering her in affection while Maya was (possibly) avoiding her. Based on her dialog in the sex scene, it seems like Josy was trying rationalize the cheating by leaving it up to MC; I don't think it's coincidence she brought up her father and Monica over dinner. She was so desperate to get away from her worries and feel something positive she was willing to cheat, but still couldn't quite bring herself to pull the trigger. It's self-destructive behavior, but it does feel believable, at least to me.
Obviously, this depends on things we don't know, and it might fall apart if and when we learn more about Maya's dad (or Josy's dad and Monica, for that matter). But personally, I find it works very well because all three parties can share the blame for the situation. Maya absolutely should have told the MC that she was still in a relationship, but it's understandable why she didn't given that she's a very private person who has clearly been burned badly talking about that relationship in the past. Josy should have either broken up with Maya or stopped flirting with the MC once it was clear he was interested in her romantically, but it's easy to see why she failed to do so. And while the MC can justifiably feel misled by Josy and betrayed by Maya once the whole thing came out, at the end of the day he was the one who kept pursuing them after they had each said no in their own way. As Josy said, he knew full well she was in a relationship when her pursued her; the only thing that really changed is that he got to feel what that was like from the other side.
Anyway, I've really enjoyed their story thus far. Hopefully all four possible 'pairings' can have a happy ending, but we'll see. That said, while I think this trio is too central to the story to ignore them, it would be good for the next episode to put more of the focus on Jill, Isabella and Sage. There's plenty of room to flesh out the new status quo of the MC and Maya/Josy through small incidental interactions. This is something the texting phone app might be good for.
It's only when the three are an item that we should keep the focus on them. Fortunately, it would make sense for that start slow, so there's still a chance for the other characters to shine now. Eventually whichever characters aren't chosen will have to fade into the background, so some level of varied interaction is going to have to happen. But hopefully that will come near the end of the game so it doesn't get unmanageable.
