Reginald is first seen eating at a picnic table in the beginning of "Tourist Trapped," with Rosanna and two others sitting at the same table.
Reginald is formally introduced in "The Legend of the Gobblewonker." He tries to propose to Rosanna while the two are fishing together. However, the proposal is interrupted by Stan, who bothers them with his pessimistic jokes and views about marriage.
In "The Hand That Rocks the Mabel," he and Rosanna are both seen putting money into Stan's "Sack of Mystery," and then later seen walking to the Tent of Telepathy and watching Gideon's show, where Rosanna catches Gideon's cape when he throws it to the audience. They are also seen eating at the restaurant where Gideon and Mabel are having their date.