Now the country crooner, 24, seems to be finding her stride, with Gossip Girl hunk Chace Crawford.
“He’s really cute,” Underwood recently told PEOPLE of the 22-year-old Texas-born actor. “I’ve met him and he seems like a really nice guy. He’s got cool hair, he’s a nice height and he just has beautiful blue eyes.”
The pair stopped by Manhattan’s Marquee nightclub last Friday, then popped into Gramercy Park Hotel’s hip Rose Bar on Saturday night.
“At one point, they were holding hands, off to the side of the table, like they didn’t want people to see,” says an observer.
Earlier this year, the American Idol champ and Academy of Country Music and Country Music Television Video Award winner was linked to Dallas Cowboys quarterback Tony Romo. Underwood is also nominated for three CMA awards this year.
Her rep declined to comment on the relationship.