Indeed, so that goes to support my theory about the Pink Box being basically owned by the MC's family, and his mom working there... well maybe not his mom exactly... frankly I just replayed the start and the shower scene and I get the impression its probably more along the line of stepmother, she refer to him in the car as 'the boy' now it could be that the Dev of this game isn't a native English speaker, however it gives off stepmother vibe far more than actual mother vibe, the only time I ever heard someone referring to their child like that typically were either men or not personally related and if the MC's dad has been basically fucking around like crazy too, its liable the MC is the fruit of either a first marriage or just one of his liaisons producing an offspring.
Also... I suspect possibly Devon might be the MC's stepsister, the picture she has that the MC has some recognition about, I wouldn't be shocked that is her mother / his stepmother. I mean she clearly isn't related to any of the other blonde mature women we have seen in the game, otherwise their would be some mention of 'hey that's my mom', so the only blonde we haven't seen her interact with to make that claim in the game is Sam. Ironically it would fit two other things, first her name being gender ambiguous, both Devon & Sam are names used by both genders, second the fact their are some hint to her being fairly slutty, which might be trying to make a point to 'like mother, like daughter'. I don't remember if Devon has ever mentioned her family, if she mention being raised by a single father it would support that theory.
As for the MC maybe we'll discover some other woman is secretly his birth mother. Another thing I noticed, the MC got a singular will to deal with... if both of his 'parents' were really his parents, shouldn't he get a separate will for his mother? This being not the case, and the fact the only things he got he get from his father's will... again lead me to really believe Sam wasn't his mother, but merely his stepmother.
Next something suspicious, the Nurse at the Hospital, the red head, she knows his girlfriend's name, yet he wasn't visited by anyone nor did he mention her name, so how does she know? It shouldn't be possible. Also you see her at the lawyer twice, so she is clearly related to his case, personally. But something else is particular, the way she talks to the MC, I don't know about how real Nurses are supposed to act, but she clearly encourage the MC to move on from his girlfriend and seek out other women... forgive me if I am wrong but it seem, she is taking way too much of a personal interest in his personal life, also encouraging pretty strongly for him to head to college... conveniently.
Which considering to some degree how Jenn has been acting weirdly, and she is working for a business likely belonging to the MC's family, it makes me wonder if she wasn't pushed to break off her relationship to the MC, and than pushed to work for the Pink Box after she went to college. Maybe she was deemed not open minded enough, and if the intent was for him to be something of a playboy, she might have been deemed as an obstacle to him developing how they wanted, so they gave her a very well paying job in compensation for breaking it off and made sure she would be considered not quite the 'girlfriend' material anymore, maybe she was told however if she went with it she would be able to get back with him later, which is why she break down if you reject her at the club, because she was lead to believe she'd be able to get back into some relationship later.
Now it would however be somewhat strange with the girlfriend clause of the will, perhaps the intention was for him to go to college, fuck around and maybe later she'd try to get back with him and fulfill the girlfriend clause at that point, however Devon sorta undercut her and sorta stole her chance to make it back to being his girlfriend, that being said if you deny Devon maybe down the line you get the chance to take Jenn back as a girlfriend. But yea maybe the intention was for him to be initiated into the life of a playboy during that expected break off time, I mean Charlie does seem to help him along into that too, and introducing him to the Pink Box before he settle with Devon, possibly again she is involved in the entire thing, being a bit of his handler in college to make sure he got the chance to fuck around before he could get serious with anyone, making sure he get a taste of the playboy life, it wouldn't be shocking to discover she encourage many of the girls to throw themselves at him for that purpose.
Another weird thing is how he got to the hospital, the 'Nurse' said he was pretty much intact, his clothes were somewhat burned... logically that mean he was extracted from the burning car, the only people that could have done that are the killers, whoever was waiting at the old gas station wouldn't have time to come rescue him if the car was burning for him to be safely enough saved. So it mean whoever killed his parents also wanted to save him, they recovered him expediently enough for him to be largely unscathed, I mean you wouldn't think whoever arrange for the assassination of a man like that would be bothered with collateral damages, unless they have vested interest in the rescued, so make me wonder if whoever did it is connected to possibly his birth mother.