15 January Jones and Josh Groban
Before Jones became the much-hated Betty Draper on Mad Men, she dated the much-loved musician Groban. More surprising than their romance, however, is the fact that Groban has yet to find a serious girlfriend since. “We were madly in love,” the singer told Details in 2013. “It was definitely my longest relationship.” Hmm… we have a feeling Megan Draper might be single soon…