Troublemaker Jamie Halstead, along with his friend Josh Crowther, were customers of Café Main Street in March 2016. Josh tried to touch one of the cakes but owner Brenda Walker slapped his hand away so Josh lied that he had had brittle bones, and Jamie chipped in that he'd need to go to hospital. Josh even threatened to call the police until Olivia Flaherty told Brenda the pair were winding her up and are idiots. Jamie hit back that at least they aren't in prison, unlike Liv's half-brother Aaron Dingle, and Josh stated only real scum ended up there. Noah Dingle stuck up for Liv by revealing his mum was in prison and she's not scum but this didn't help as Josh suggested Liv's mother was aware Liv's father sexually abusing Aaron. The boys left the café after telling Brenda that the place was garbage.
The following week, Jamie and Josh returned to the café and Brenda gives them a second chance. Jamie talked to disinterested Liv whilst Josh chatted up Gabby. They four skived off school and drank vodka at Gabby's house before being thrown out by Gabby's step-mother Laurel Thomas. A few months later, Josh and Jamie turned up in David's Shop looking for Jacob Gallagher and before they left, Josh stole a copy of Tracy Metcalfe's erotic novel and they later tormented Jacob by reading passages containing details of Tracy's sex life with Jacob's surrogate father David Metcalfe.