This is still brroken, but at least it doesn't freeze up any more.

config/punctuation/default.conf

@@ -46,24 +46,20 @@ _:===:line
 [customDict]
 
 [emoticonDict]
-<{-.-}>:===:Raves
+(?:['|"| |^])(<{-\.-}>)(?:['|"| |$]):===:Raves
-8-):===:smile with sunglasses
+(?:['|"| |^])(8-\))(?:['|"| |$]):===:smile with sunglasses
-:-/:===:confused
+(?:['|"| |^])(:-/:)(?:['|"| |^])===:confused
--.-:===:bugged
+(?:['|"| |^])(-\.-)(?:['|"| |^]):===:bugged
->.<:===:laughing
+(?:['|"| |^])(>\.<)(?:['|"| |$]):===:laughing
-8-X:===:skull
+(?:['|"| |^])(8-X)(?:['|"| |$]):===:skull
->:):===:evil smile
+(?:['|"| |^])(>:[?-]\))(?:['|"| |$]):===:evil smile
->:-):===:evil smile
+(?:['|"| |^])(:/)(?:['|"| |$]):===:confused
-\o/:===:Hurray
+(?:['|"| |^])(8\))(?:['|"| |$]):===:smile with sunglasses
-:/:===:confused
+(?:['|"| |^])(:D(?:['|"| |$]):===:laugh
-8):===:smile with sunglasses
+(?:['|"| |^])(;\))(?:['|"| |$]):===:wink
-:D:===:laugh
+(?:['|"| |^])(XD)(?:['|"| |$]):===:LOL
-;):===:wink
+(?:['|"| |^]):[?-]\))(?:['|"| |$]):===:smile
-XD:===:LOL
+(?:['|"| |^])(->)(?:['|"| |$]):===:arrow right
-:-):===:smile
+(?:['|"| |^])(<-)(?:['|"| |$]):===:arrow left
-:):===:smile
+(?:['|"| |^])([Oo][Oo])(?:['|"| |$]):===:WTF?
-->:===:arrow right
+(?:['|"| |^])(\^\^)(?:['|"| |$]):===:enjoy smile
-<-:===:arrow left
-oO:===:WTF?
-Oo:===:WTF?
-^^:===:enjoy smile