In an interview with Billboard Walker stated, "Music should provoke some type of emotion in people, whether it be sad, romantic, or happy, and 'Then What?' is definitely a pick-me-upper." He also stated, "As an entertainer, being on the road so much, I hope to have a song that will go over good live. And this is probably the best song live that we've had since my first single."
Larry Flick of Billboard wrote "The island feel of this track's production gives Walker's new single a fresh, bouncy, and totally appealing sound. Walker's vocal is teeming with personality, and this little number should find instant favor among programmers looking for a sunny winter offering."The Dallas Morning News wrote, "A quasi-calypso ditty - you can't get more innocuous than this - the song's accompanying video comes complete with Gilligan's Island motif and the usually stiff Mr. Walker donning sandals and singing with his denim shirt wide open.
Kevin John Coyne of Country Universe listed "Then What?" as the 377th greatest contemporary country single and wrote, "With this out-of-left-field smash, Walker has the dubious honor of bringing Caribbean-flavored country back to the forefront." 
This song debuted at number 60 on the Hot Country Singles & Tracks chart dated December 27, 1997. It charted for 27 weeks on that chart, and peaked at number 2 on the chart dated April 11, 1998. It also peaked at number 65 on the Billboard Hot 100.