Till arrived in Money, Mississippi on August 21, 1955. On August 24, he and cousin Curtis Jones skipped church where Wright was preaching, joining some local boys as they went to Bryant's Grocery and Meat Market to buy candy. The teenagers were children of sharecroppers and had been picking cotton all day. The market was owned by a white couple, 24-year-old Roy Bryant and his 21-year-old wife Carolyn, and mostly catered to the local sharecropper population. Carolyn was alone in the store that day; her sister-in-law was in the rear of the store watching children. Jones left Till with the other boys while Jones played checkers across the street. According to Jones, the other boys reported that Till had a photograph of an integrated class at the school he attended in Chicago,[note 1] and Till bragged to the boys that the white children in the picture were his friends. He pointed to a white girl in the picture, or referred to a picture of a white girl that had come with his new wallet, and said she was his girlfriend. One or more of the local boys dared Till to speak to Bryant.
The facts of what took place in the store are still disputed but according to several versions, including allegations from some of the kids standing outside the store when Till walked in, Till may have wolf-whistled at Bryant. A newspaper account following his disappearance stated that Till sometimes whistled to alleviate his stuttering. His speech was sometimes unclear; his mother said he had particular difficulty with pronouncing "b" sounds, and may have whistled to overcome problems asking for bubble gum. According to other stories, Till may have grabbed Bryant's hand and asked her for a date, or said "Bye, baby" as he left the store, or "You needn't be afraid of me, baby, I've been with white women before."
Bryant testified during the murder trial that Till had made sexual advances and asked her for a date. In her testimony, Bryant alleged that Till grabbed her hand while she was stocking candy and said, "How about a date, baby?" She said that after she freed herself from his grasp, the young man followed her to the cash register, grabbed her waist and said, "What's the matter baby, can't you take it?" Bryant then allegedly freed herself, and Till told her, "You needn't be afraid of me, baby," used "one 'unprintable' word" and said "I've been with white women before." Bryant also alleged that one of Till's companions came into the store, grabbed him by the arm and ordered him to leave.
Till's cousin, Simeon Wright, writing about the incident decades later, challenged Carolyn Bryant's account. Entering the store "less than a minute" after Till was left inside alone with Bryant, Wright saw no inappropriate behavior and heard "no lecherous conversation." Wright said Till "paid for his items and we left the store together." The FBI also noted in their 2006 investigation of the incident that a second anonymous source, who was confirmed to have been in the store at the same time as Till and his cousin, backed this claim as well.
In any event, Bryant was so alarmed she ran outside to a car to retrieve a pistol from under the seat. Upon seeing her do this, the teenagers left immediately. It was also acknowledged that while Bryant was running to her car, Till whistled. However, it is disputed whether Till whistled towards Carolyn or towards a checkers game that was occurring just across the street.
One of the other boys ran across the street to tell Curtis Jones what happened. When the older man with whom Jones was playing checkers heard the story, he urged the boys to leave quickly, fearing violence. Bryant told others of the events at the store, and the story spread quickly. Jones and Till declined to tell Mose Wright, fearing they would get in trouble. Till said he wanted to return home to Chicago. Roy Bryant was on an extended trip hauling shrimp to Texas and did not return home until August 27.