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Hilbert and Hilda are not currently going out, or at least that is what I am picking up from the the current version that I have played (v1.0.2c). Currently it seems that Hilda has feelings towards Hilbert, but Hilbert currently seems to have no romantic interest in Hilda. It could be possible that if the main character pursues Hilda in a romantic way that Hilbert may realize that he has feelings for her or at the very least realizes that he misses her not spending as much time around him.
Brendan and May however are a different story, for one they seem to be together but most of the time we see them together they just seem to be acting like good friends rather than a couple. There are a few elements that are in the story of the current demo that could effect their relationship in a negative way. Such as Brendan saying that he is afraid of commitment in front of May, which is a bad thing to say in front of the person you are dating. Furthermore the way way that Brendan acts towards May when they are together is more like close friends then an couple. Even if two people like each other, if one of them feels like the relationship isn't going anywhere or that there partner isn't taking the relationship as seriously as they are, it can lead that a break up. The same is true if one partner feels like the other is rushing the relationship or is demanding too much of their time. I can pretty easily see the two of them taking a break, or at least having some time apart because Brendon said or did something to upset May, or because May wanted Brendan to show more commitment then he is currently comfortable with in their relationship. Depending on how events would proceed from that point would effect whether their bond would become stronger or if they would just stay as friends.
The most interesting thing in this kind of development is that Brendan is one of your potential roommates, and if you did choose Brendan as your roommate then you will have more influence on outcome of their relationship. And if you do romantically pursue May then it will obviously put a strain on your relationship with Brendon.
While that is an interesting concept, harem routes only tend to work if there are 2, or at most 3 partners for the main character, any more then that and it loses focus and substance. needless to say there are a lot more then 3 potential heroines, and considering that harem routes are normally unlocked after beating every other route, it would be a nightmare for both the team to develop and for us to reach.
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