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January Jones (2010-2011)

In November 2009, Sudeikis met "Mad Men" star January Jones when she appeared on "Saturday Night Live" as a host. However, their dating rumours didn't begin until July 2010 when People reported the two were seen "making out all night" at an ESPYs afterparty. Around the same time, there were also rumours going around that Jones had been visiting Sudeikis at work while he was filming a movie.

Sudeikis reportedly confirmed their relationship a few weeks later while appearing on "Lopez Tonight" (via Huffington Post). When asked if he had seen Jones "naked and everything," the actor initially responded by saying he "didn't want to get into it," but then joked, "I'm kidding. I do want to get into it! I do, and I have!"

Shortly afterward, Jones responded to Sudeikis's quip in an interview with People at the 2010 Emmys. "He's never seen me naked, nor will he after those comments," she said, before adding, "I think he handled that question very well. He made a joke of it. What was he supposed to say?"

Despite the incident, the pair continued to date until January 2011 when People reported they split. "They've been on and off for a few months and then the long distance kind of ended it," a source told the publication.

Image Source: Getty / Jeff Kravitz