Dee Reynolds and the Waitress despise each other but oddly enough neither has any close female friends. The Waitress sleeps with Dee's twin brother Dennis in "Charlie Has Cancer". Dee and the Waitress sat next to each other in Trig class in High School but Dee does not remember her. (The Waitress Is Getting Married). Dee first officially met the Waitress when Dee and Charlie were taking Tommy Doyle (the boy Charlie thought was his son) to the mall shopping. The Waitress was mentoring a young Mexican girl as part of a Big Sister program. Charlie had tried to imply Dee was his girlfriend but Dee corrected him. (Charlie Wants An Abortion).