Simon is an English man whom Elaine briefly dated in "The Soup."
Elaine met Simon in England while traveling with Mr. Pitt. Simon flies to New York using Elaine's frequent flyer miles, but in the taxi on the way from the airport, he makes rude comments toward Elaine, dampening her excitement about his arrival. Elaine and Simon's relationship does not go well, as he is constantly borrowing money from her and is always out. Later, Jerry gives Simon an Armani suit given to him by Bania. Simon, while wearing the suit, blatantly flirts with a woman in front of Elaine, and informs her and Jerry that he has a job interview. Elaine tells Bania that Simon has his suit and Bania goes to confront him.