Before Carrie Underwood settled down with NHL star Mike Fisher, she dated a couple of A-listers, including former Dallas Cowboys quarterback Tony Romo and actor Chace Crawford.

The country singer began dating Romo in 2007 after her winning turn on “American Idol.” However, the pair split just a few months later.

Even after the breakup, Romo had only positive things to say about Underwood. “I’ve been lucky to get to know [Carrie]. We’re friends,” the quarterback told Sports Illustrated.

In late 2007, rumors of Underwood dating the “Gossip Girl” fame, Chace Crawford began surfacing. Soon after, a source told People that Underwood apparently broke “Chace’s heart.”

Opening about his relationship with the country singer, Crawford told People Magazine, “I learned a ton about dating someone in that kind of spotlight [...] but no regrets.”