The Freeheld star opened up on Tuesday's Ellen, telling her that while the two worked together on The Daily Show, they met long before that at the Second City Theater in Chicago. Nancy was taking classes at the comedy theater, where Carell was an employee, while working at the bar across the street and he would stop in to flirt with her, though they were both too shy to ask each other out.
"The conversation would go something like, 'Hey, you know, if I were ever to ask a woman out, it would be someone like you. Exactly like you,'" Carrell admitted with a laugh. "And she'd say, 'If a guy like you were ever to ask a woman like me out, I would definitely do that.'"
"This went on for weeks," Carell continued. "Other people at the bar at the bar must have been like, 'Just do it! Put us all out of our misery.' And finally, we did. It was great."
The comedian told Ellen that he was finally the one to pull the trigger, though thinking back to that nervous moment brought back Carell’s memory of the first time ever asked a girl out on a group date in the eighth grade. The comedian recalled nervously phoning up his potential love interest and asking her to the movies.
"She got on the phone [and I said] ‘Lisa, would you like to go to the movie, a group is going on Friday, and she just said ‘No, I dont'," Carell recalled. "No excuse, nothing, just like, ‘I really don’t want to do that.'"
It seems like that experience might have led to his nervousness around his future wife, as the actor admitted, "I never asked another girl out on a date. I never had the guts to actually call a girl on the phone after that."