20 Weird Celebrity Couples: Is She Really Going Out With Him?! (PHOTOS)

She: Actress best known for her role as Betty Draper on Mad Men; previously linked to funny men such as Ashton Kutcher, Seann William Scott, and Jason Sudeikis; has earned a reputation for being an ice queen

He: Operatic singer whose first four solo albums have gone multi-platinum; #1 best-selling U.S. artist of 2007; broke into the world of acting with appearances in Glee, Crazy Stupid Love, and The Office   

Status: January and Josh dated for over three years, beaking up in the middle of 2006. In September 2011, January gave birth to her son Xander, though the father’s identity has not been revealed.