Coulda Woulda Shoulda is a form of second-guessing or regret. According to Urban Dictionary, one definition: Meaning that it is of no use to dwell on what should have (shoulda), could have (coulda) or would have (woulda) happened/been done. Said as an attempt to shorten a discussion that focuses on the past, thus providing no solution to an actual problem. “The saddest … [Read more...] about Coulda Woulda Shoulda