Thomas "Trip" Hesburgh III (Robin Dunne). He is a journalist and George's first serious relationship.

George found herself liking Trip a great deal and became extremely upset when she thought that Trip was her reap, Thomas Hesburgh Jr. Though it was soon revealed that Trip was Thomas Hesburgh III and she was supposed to reap Trip's father instead.

Despite being raised in a wealthy family Trip seems to be very unhappy with his life, tired of the social superficialities of his wealthy upbringing, a thing his older sister Ashley always scold him about. He became George's first lover and called her his girlfriend, however after spending the night with George, he never called or sought her out again, sending the girl into a rage. Trip and Ashley know George by her real name (rather than by her Millie alias), a revelation which Mason chides her for (although all the other reapers introduce themselves to the living with their real names throughout the series).