Skwoulda Share definition Flag Hybrid combo of shoulda-coulda-woulda, should have-could have-would have, etc. Pronounced skwood-eh. classified in the same phylum as scoulda. I skwoulda invested in gold mining stocks. Skwoulda by Ace B May 23, 2006 0 0 Get merch Get the Skwoulda mug. Buy Now — $32.95 See more merch