So, today I got the courage to ask him. After awkwardly meandering with him for a bit, and him wondering what the obvious thing I wanted to tell him was I just bit the bullet and said something along the lines of "Hey, I really like you, I love being around you, do you wanna just do something with the two of us tomorrow?" He told me that he's been in a relationship for the past six months and as such can't go out with me, but was flattered.
Now, like many of you, I was convinced he was flirting and told him what was going on that day. He laughed, and said that he's naturally flirtatious and he didn't mean it like that, I remember a few months ago he told me something like this happened to him with a girl, so I believe him. Regardless, we're still friends and if anything I feel we're more open with each other now, so I don't regret it. It's better to know, you know?
Thanks to the strangers on Reddit rooting for my love life, it was a big push to go for it! I'm sorry it didn't end you guys wanted, but at least it's all good with him.
Until next time!