Sure Thing was first presented at Manhattan Punch Line's Festival of One-Act Comedies, New York City, in February 1988. The director was Jason McConnell Buzas. The characters of Bill and Betty were played by Robert Stanton and Nancy Opel, respectively. 
Sure Thing was part of Ives’ original six-play collection, All in the Timing, which premiered Off-Broadway in 1993 at Primary Stages, and was revived at Primary Stages in 2013. Ives won the Outer Critics Circle John Gassner Award for Playwriting, 1993-1994.