Rachel Cannon (Chloe)
Out of all the girlfriends he had in the show, Chloe was the one Charlie wanted to get rid of the most. As you undoubtedly know about Charlie, he was never truly ready to commit to a relationship, which was what drove him insane about Chloe.
But when Fernando, the handsome handyman played by none other than the Latin singer Enrique Iglesias, comes by to fix Charlie’s deck, Chloe has eyes for no one but him. This drives Charlie insane, and he even dresses up as a younger version of himself before interrupting Fernando and Chloe’s getting-it-on session. In the end, he bribes her to come back, and Fernando is out of the picture.