Rachel Cannon, Actress: Fresh Off the Boat. Rachel Cannon was born in Tulsa, Oklahoma, USA as Rachel Wells. She is an actress, known for Fresh Off the Boat. Rachel Cannon - Two and a Half Men. elnino - 08/05/08 - views, 0 replies. FORUM THREAD. Rachel Cannon is an American actress who portrayed the recurring role of Chloe, Charlie's girlfriend, in seasons 4 and 7 of Two and a Half Men. Rachel Cannon Character Chloe Season(s) S4, S7 IMDb profile.