My first visual novel was Umineko no Naku koro ni. I started reading it because the girl I liked was reading it (lol) and because I was really into Higurashi when it was airing. ...Then Umineko took over my life, whoops!
Though I'd always had this weird interest in eroge. It started when I was 11 or 12 and was part of roleplaying communities where we used anime style CGs, so I found out about titles through the art I'd use. At the time my computer only had like 2GB of storage (?!) so I could never download games, and then for years I never tried anything on my Mac. So instead I just LOOKED at a lot of games and retained a lot of knowledge about various titles without actually playing them myself?? But once I had Umineko running, I suddenly felt motivation to try and get games running on my Macbook. So here we are.
My first eroge was Shuffle! purely because it was the first eroge I'd heard of years ago and I, for some reason, felt like if I ever started playing eroge, it'd have to be my first one. Wasn't really worth it tbh.