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