Can we take a moment to discuss the fact that Eva spent several months reworking Stan's storyline, only to present something that was virtually unchanged? Thinking about it now, I realize how bad it actually is, which makes you wonder how she decided that she had achieved any meaningful differences at all.
Honestly, all the problems with Stan are still there. Sure, he might be slightly less incompetent, and maybe not as apologetic for his own existence, but at the end of the day, he is still a self-pitying creep. No matter how many encouraging words you choose to give as Lena, he is still exactly the same. He goes on and on and on about how no women would ever find him attractive, how he is just a bother to everyone else, and how no one likes him. And to be fair, he would be right, because a person who thinks like this would become extremely unappealing to spend time with.
As an additional sort of "fuck you", he thanks Lena for all the encouragement by masturbating to her pictures in broad daylight and spying on her when she has sex. I mean, wow! Those definitely aren't some extremely unsympathetic character traits that makes him more repulsive than he already is. I was actually highly surprised when I saw that the scene where he is caught masturbating to Lena is still in the game, because that is one of Stan's most unforgivable and damaging moments This, of course, makes it even harder to justify why you would ever seek a relationship between him and Lena.
It is just regrettable that Stan's character still has so many flaws. I think that Lena's love interests are already much worse compared to Ian's, with many of them having the potential to immediately disqualify themselves through completely natural choices (i.e., not forgiving Axel for cheating, rejecting Robert for being a pushy douche, rejecting Seymour for being a manipulative asshole, and telling Louise about Jeremy). So, making Stan a self-pitying creep doesn't really help. And keep in mind that this is coming from someone who actually looked forward to Stan's storyline, as this would allow for Lena's complete depravity by fucking someone who clearly is not in the same league as her.
Anyways, I am not going to be all negative, because I actually do have a few ideas for how his storyline could have been infinitely better. First of all, make him a proud nerd. He can still be awkward and shy, but allowing him to actually have some interests that he could energetically discuss, would make him instantly more likeable. Even though Lena might not share these interests, I could at least believe that she would see some charm in a person who dares to be themselves, and who shows some true passion for something.
Second, make him be not-a-creep (or at least not visibly creepy). If he secretely jerks off to all of Lena's pictures, that is fine, just don't have her catch him doing it. And if you absolutely must have some element of Lena discovering that he masturbates to her, do it in a more lighthearted way, i.e., finding out he is subscribed to her Stalkfap or has her as his computer background. If you couple this with them having a pretty good and easy-going relationship, she could tease him about it as a friend, because she knows that, at the end of the day, their relationship is good and he treats her with respect.
Third and finally, make Stan more competent in their photoshoots/Lena's content creation. It makes perfect sense that he acts as an amateur the first time, and that Lena has to direct him. However, when he goes to edit the photos, he can surprise Lena by delivering photos that were edited with a quality way above her expectations. Upon asking how he managed this, he explains that he took some courses, watched some tutorials, as to really give her the best result possible. Then, we can see Lena really appreciate the effort he put in.
During the second shoot, it starts off just like the first, with Lena having to direct Stan to a large extent. She asks how the photos are turning out, and Stan answers, hesitantly, that they are okay, but that they are missing the X-factor. He could then propose a pose or an angle, which turns out to be really good and the best photo of the entire shoot, Once again, this is due to the fact that he has been investing a lot of time in course and tutorials, which really impressess Lena. He can also provide input on what her Stalkfap subscribers would enjoy the most.
Either way, what you end up with is a situation where Stan is clearly making a great effort for Lena, which facilitates a relationship between them in two ways. On one hand, it could happen because Lena simply starts to appreciate Stan, because he is treating her very well, and because they might connect over one of the interests Stan is passionate about. On the other hand, it can occur in a more porn-like way, where she decides to reward him for all of his efforts with a blowjob, and at a later stage, sex (which could be more a fun thing for Lena given her lax attitude towards sex). Or, when her Stalkfap subscribers ultimately ask for boy-girl content, it could be natural to ask Stan, because, after all, he is the one that has helped her out the most, so it makes sense that he is rewarded for it.
If their relationship developed in this way, rather than Stan wallowing in self-pity and acting like a complete creep, I think the route would be much more appealing to play, and would improve tremendously. Regrettably, it will probably never happen, but one can't help speculating in the ways in which this part of the game could be easily enhanced.