Interesting topic. I think I’d have to start first by figuring out whether they would work as a friend first, because right now I’d say I’m more interested in making new friends rather than holding hands and drinking milkshakes.
The hardest part for me would be the initial meeting of any would be potential friend/boyfriends/girlfriends. I have social anxiety, so I don’t chat up new people very often, and extended eye contact tends to really freak me out, especially with people I don’t know very well, but even my oldest friends of 10+ years have noticed it too. Obviously, it’s also kind of hard to say how this entire thing would work in the first place: Do I recognize them exactly from the game/anime or am I just somehow drawn to this person and interested in them naturally? If it’s the former, in my case, I think that would intimidate me all the more, and reduce my likelihood of initiating with them at all. That being said, all the close friends I have now are ones that initiated things with me, so I suppose it’s still possible, even if I did recognize them. If the latter, then maybe.
With that out of the way, I’ll consider my favorite female character at the moment and explore the possibility of an actual friendship, then as a potential girlfriend. I’ve always really adored Kurugaya since watching the LB! anime, and now after digging into the VN, she has definitely been solidified as one of my favorite characters in any anime or VN I’ve seen yet (female or male). I think the reason I’m drawn to her is because I feel like she’d fit right in with my circle of friends. We all mess with each constantly, make stupid and perverse jokes, ditch class, been in fights, and the like. In theory, assuming the circumstances were right and I didn’t make a total ass of myself, I’d like to think we could be decent friends.
As a romantic interest, the only girls I’ve been really close to have been tomboyish and independent, and therefore mostly self-reliant, all of which are traits I believe she has. Ultimately, my ideal thought for a relationship with someone is that I’d like us to remain individuals, even if we are together. I get bored easily with the usual small talk crap that I have with acquaintances, coworkers, casual friends, or friends of friends, and I don’t want someone to constantly be calling or messaging me because they haven’t heard from me in a few hours or a day or two. Sometimes I like to just go off and take a walk in the woods and be alone for a bit, but sometimes I want someone with me. That’s a bit selfish, yes, but that’s the kind of relationship I have with my friends now; we all agree to it, understand it, and work around it. That’s the idea of what I’d want from a romantic relationship as well, (at least early on, and see how things go from there) and (again, in theory) based on what I know about her, I’d like to think Kurugaya might be able to roll with that, but that could just be me projecting here.
At the very least, I’d be down to give either a friendship or a relationship a shot. Despite my initial meeting issues, I wouldn’t be worried about any long-term relationships problems, since those will come up regardless of the context. I don’t dislike anyone who I’ve fallen out of love or touch with, and if things didn’t work out, then I’d just hope we had a good time while it lasted.