I've thought about that. It might revolve around their high school member graduating. I could just see Jigu getting there first and being too nervous at the meeting point despite noticing others showing up. They don't approach him either.
But Yeowoon shows up and they immediately know it's him. Then, after a few little introductions, he calls Jigu over and the high schooler breaks the ice, showing Jigu's still the pestering *sshole they know. Then, the whole thing would become a vibe, chuckles galore at finding out the two of them are the neighbors they both complained about, and THEN that they're dating.
We can only hope.

jigu i am quite fond of you you soaking wet cat ughh i love both of them soo much i hope we get a sequel where all guild members meet irl theyre all so cute