Aw, I'm glad you like him, I aim to provide all the funny squid times I can manage.

AND YES I believe they would've run into each other multiple times, and would've chatted about the sweets they like (though in Lovecraft's case, it's probably "EVERY SWEET"). He probably wouldn't show off his tentacle self during those times, but still, I imagine they'd find in each other a sweet-loving kindred spirit.