Entertainment Weekly gave the album a positive review, stating: "To Mellencamp's credit, even though 'Whenever We Wanted' delivers his signature rock & roll punch, he doesn't try to. That Mellencamp still has the courage to make depressing assessments in a pop context is a victory that outweighs the record's other shortcomings."
Despite calling Whenever We Wanted one of the best records he had ever made during his 1991 promotional radio tour to support the album, Mellencamp's opinion of Whenever We Wanted has since diminished. He told Alan Sculley of Call Newspapers in 2005: "There were some records that I really wasn't there for. I mean, I did a record called Whenever We Wanted, which really isn't a very good record. I mean, I was there, but I was painting. I'd be hours late for sessions just because I was in the middle of a painting. That's not good doing that kind of thing. Human Wheels turned out pretty good, but I kind of was doing the same thing during Human Wheels."