The Waitress (It's Always Sunny in Philadelphia)

Character Overview

The Waitress is the most frequently featured character of the recurring cast of It's Always Sunny in Philadelphia. The Waitress is not a part of "The Gang", but frequently finds herself involved in The Gang's antics due to being dragged in as a pawn for one member to get revenge on or humiliate another member. Despite having an on-again off-again crush on Dennis Reynolds, The Waitress despises the gang, most notably Dee Reynolds, who is responsible for most of The Waitress' involuntary involvement with The Gang.

The Waitress is openly stalked by Charlie Kelly, who is enamored with her, but the Waitress constantly rebuffs him. She has numerous restraining orders against him, but that doesn't stop him, as she begins to allow him to continue his obsession when she realizes he has been helping her avoid danger by testing her food for poison and putting vitamins in her shampoo.

The Waitress is "easily forgettable" according to The Gang, who only refer to her as "The Waitress", with the only one who possibly knows being Charlie. Her name tag was also missing at the high school reunion and Dee forgot she went to school with her, believing that they met ten years later when Charlie introduced them.

The Waitress has worked a number of menial side jobs alongside her occupation as a coffee shop waitress, including a manager of a corporate pub, a booth manager at a carnival, and a food delivery woman. She struggles financially, and eventually ends up in a women's shelter.

The Waitress is an on-again off-again alcoholic, who has been involved with Alcoholics Anonymous for years, but as a result of The Gang's action, she repeatedly relapses. When intoxicated, she is rude and belligerent.

Charlie Kelly

Charlie Kelly openly stalks The Waitress, and keeps a journal of all her activities and whereabouts day to day, but Dee steals it in return for a favor from The Waitress. It is likely he has begun a new one. On occasion, he has hired other people to stalk her and report her whereabouts. The Waitress has issued several restraining orders against Charlie, but amends them to allow Charlie to come within a fifty-foot radius after many of the tasks Charlie completes for her, including putting vitamins in her shampoo, testing her food for poison, and killing rats for her apartment go unfinished, and The Waitress realizes that Charlie is valuable to her life as he is the only person who cares about her well being. She also gets jealous when Charlie finds an interest in a new woman, demanding to know who "that bitch" is.

Charlie goes to great lengths in order to woo The Waitress, including trying to impress her by demonstrating his paternal nature by pretending to raise other people's babies. He also fabricates a story about him having terminal cancer when he sees her wearing a Lance Armstrong bracelet. He also attempts to connect with her by pretending to be an alcoholics he could continue to spend time with her at Alcoholics Anonymous, where he continues to guilt her into being her sponsor.

Charlie once proposed to The Waitress, but she declined.

Dennis Reynolds

Dennis does not care for The Waitress whatsoever, however, she is notably infatuated by him. When together, she seems to forget herself and follows Dennis blindly and will do most anything to get his attention. Her most extreme cases of trying to grab Dennis' attention include being Charlie sponsor for Alcoholics Anonymous, grinding on homeless people, and (although weaseling out of it) sleeping with Charlie. On several occasions, Dennis has used her undying love for him against her, mostly to blackmail Charlie into doing whatever it is Dennis would like. He has slept, flirted, dated, and been in overall close sexual contact with The Waitress in order to do said blackmailing, usually involving "climbing up the ranks" of Paddy's, getting out of Charlie work (earlier in the series) or general tomfoolery.

Throughout the course of the show, Dennis has slept with The Waitress several times, of which he records their sex, giving it a "one star" rating in terms of enjoyability and fun.

Mac

Mac has little relationship with The Waitress outside of trying to sleep with her in order to upset Charlie, on account of Charlie smashing one of Mac's "Project Badass" tapes. This is later revealed to be untrue, as the tape Charlie was smashing was actually Frank and The Waitress' sex tape that Charlie mistakenly watched.

Frank

The Waitress sleeps with Frank in order to make Dennis jealous of her. She does this under the guidance of Dee, who is being instructed by Charlie, in order to get The Waitress (through a convoluted plan) to like him. Unbeknownst to anyone for a long time after, Frank records their sex. His toupee falls off during their love-making session.