It tells the story of the song's events in retrospect as the narrator looks over the damage he incurred from his wild night with Becky (such as pulling a corn leaf from the undercarriage of his Ford Ranchero or looking at the scar he picked up from his fight with the "mountain of a man with a 'Born to Kill' tattoo", which apparently is Becky's ex-boyfriend) while wondering if it was really worth it. The video features Lauren Elaine as "Becky", the white tank-top wearing "beauty from South Alabama". Elaine also appears in "How Am I Doin'", "Lot of Leavin' Left to Do", and "Am I the Only One" as the same character. The video was shot in New Braunfels and Kingsbury, Texas over 3 days in May 2003. The video opens the night of the date when Bentley takes Becky back home. She asks if he would want to do it again, and though he is unsure, he reluctantly agrees. Throughout he is seen performing with his band, and sitting on the hood of his truck looking at pictures of the date he can't remember. "What Was I Thinkin'" reached its peak position of number one on the "Billboard" Hot Country Songs charts dated for the week ending September 27, 2003. The song succeeded Alan Jackson and Jimmy Buffett's duet "It's Five O'Clock Somewhere" at this peak.