Jerry and Elaine had dated for a while before the show started. They started dating in 1986 (as revealed in "The Truth"; per "The Betrayal", this would have been shortly after Jerry moved into his apartment and Elaine first moved to New York, suggesting Jerry was her first New York boyfriend), then dated for three years until 1990, indicating they started dating in late 1986 and broke up in early 1990; however, in "The Deal", Elaine states they only had sex 37 times, and in the same episode Jerry states he thought it was 25 times, numbers which, given the length of their relationship and post-relationship promiscuity, seem implausible. In any event, during conversation in "The Deal", Jerry and Elaine make clear that their breakup was not due to sexual issues; the precise reasons for their breakup are never elaborated on. However, in "The Stakeout", Jerry tells his parents that the reason for the break-up had to do with fighting too much and "physical chemistry".