Gilbert briefly dated Pam Hobsworth after the pair had met at a singles evening and went out on a double date to the tea room at The Pines Hotel with Vanessa and Bill Webster. Since Pam claimed to be a concert pianist, Vanessa suggested she should play the piano for everyone in the establishment. However, Pam fooled Gilbert by telling him that she had injured her wrist and needed him to get some ice. Gilbert went to seek assistance, but Vanessa saw through Pam.