Toby was a guy who Kris Fisher and John Paul McQueen spotted at the SU Bar in March 2008. Making a bet over being the first to kiss a guy, Kris pushed John Paul to speak to Toby first. John Paul managed to win the bet with Toby, but ended up giving Toby his number. Walking home with Kris, John Paul began getting texts from Toby. The next morning, Toby found John Paul at the Hall of Residence, giving him a kiss on the cheek and revealing that he had brought John Paul breakfast.
John Paul told Toby that he needed to meet with one of his sisters, to which Toby said that he would join him and called him "babycakes". Kris - enjoying John Paul's discomfort - had Toby meet him and John Paul at the SU Bar at 7:30pm. John Paul struggled to tell Toby where they stood and ended up telling him that he was having an affair with a married man. Toby was left disgusted and, about John Paul's jeans, said "two words: Simon Cowell", told him to have a nice life "loser" and stormed off.