richie

-you did
-your biggest fear is losing richie
-so after IT appeared to torment you, you ran to his house
-when he answered the door you hugged him tightly
-"i love you so much, richie."

bill

-he did
-after he saw georgie in the basement
-you were staying over that night
-he came running upstairs crying
-"y/n, i love you. i don't want to lose you too."

eddie

-you did
-it kinda just slipped out
-"god damn, i love you."
-you don't even realise you said it
-eddie.exe has stopped working

stan

-you both said it at the same time
-"i love you, stan."
-"i love you, y/n."
-giving each other strange looks
-but then dying of laughter

beverly

-she did
-really causal about it
-"love you, y/n/n."
-"uh, um... i... love you too, bev."
-bev just laughs at hiw flustered you got