January Jones and Josh Groban dated from 2003 to 2006, and more than six years after that two-and-a-half year relationship ended, Josh called it his longest relationship. He low-key hasn’t had another relationship last that long since. His relationship with Kat Dennings from 2014-2016 came close, but it looks like January was the love of his life. Josh has had a weird dating history since the early 2000s, being linked to Katy Perry, April Bowlby, Selma Blair, and possibly Michelle Trachtenberg. Meanwhile, January had a baby from an unknown (to us) father, strongly advocated for eating your own placenta, and started dating Nick Viall.