Unlike her brother Trevor, Ruby is an honest and kindhearted person. She genuinely likes Charlie, and (unlike most women) is not bothered by his bizarre behavior. She breaks down crying after Charlie calls her a "stupid little rich slut".
In "Charlie and Dee Find Love" (Season 8, Episode 4) Ruby and her brother Trevor meet Charlie and Dee after Trevor rear-ends Dee's car. She and Charlie appear attracted to each other at first sight. Trevor proposes that the four go on a dinner date.
At the dinner, Charlie and Dee pretend to be members of a wealthy family. However, they become stressed and eventually break down, revealing the truth. Ruby is relieved at this, telling Charlie and Dee that she likes them because "you're not like anyone we know."
The next day, the rest of the gang follows Charlie and Dee to the Taft estate. Dennis, convinced that Ruby is plotting to humiliate Charlie, decides to play tennis on her team in an attempt to "extract her plan". He begins flirting with her and even removes his shirt, but Ruby is unimpressed. After Charlie gets a shoulder cramp, Ruby begins massaging him; however, Frank and Dennis are still convinced that she is just "sinking in her hooks".
Later, Ruby and Charlie are walking together down a street. Charlie admits that there's another girl who's the love of his life, and says he has to let go of her before he's able to go any further with Ruby. At that moment, the two are confronted by The Waitress, who mistakenly believes that Charlie is poisoning her. When Ruby says that Charlie has been with her for the past couple of days, The Waitress angrily demands to know who "that bitch" is. Charlie responds that she's his girlfriend, and kisses Ruby.
At a party thrown by Trevor and Ruby's father, Dennis brings forth an incriminating tape, revealing that Trevor had given Mac an insider-trading tip while the two were wrestling. He then accuses Ruby of "playing her own games", and takes out his phone. Over the phone, Frank tells Charlie that "someone accidentally hit The Waitress with my car...I mean, 'their' car." The Waitress herself, lying in a hospital bed, asks Charlie to help her.
Hearing this, Charlie decides to leave the party. Ruby, visibly upset, tells Charlie that she wasn't playing any games, and that she genuinely likes him. However, Charlie replies that he was aware of this all along, and that he was merely using Ruby to make The Waitress jealous. He also claims that she is not a "woman of quality" because she was willing to sleep with him shortly after meeting him, and goes on to call her a "stupid little rich slut". Hearing this, Ruby breaks down and begins crying.