Celebrity Carrie Underwood and Chace Crawford Broke Up Via Text Interestingly, Underwood’s ex-boyfriend Tony Romo is now Crawford’s brother-in-law. By Isabel Jones Isabel Jones Instagram Twitter Isabel is an Oregon-born and Brooklyn-based writer and editor with a special interest in pop culture. InStyle's editorial guidelines Published on March 25, 2021 @ 03:08PM Pin Share Tweet Email Photo: Getty Images/InStyle Who: Teen Choice Award-winning actor Chace Crawford, 35, and Grammy-winning singer Carrie Underwood, 38. How They Met: According to Cosmopolitan, the American Idol alum and Gossip Girl star met in May 2007 at the Hollywood nightclub Hyde. The media caught wind of the relationship that fall, as Gossip Girl became the teen drama du jour. In October, People reported that Underwood had called Crawford "really cute," noting, "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." At that point, the couple was a fixture at early-aughts nightlife destination Marquee and had been photographed together at Justin Timberlake's since-shuttered restaurant Southern Hospitality. Why We Loved Them: May I redirect you to this sentence: "the American Idol alum and Gossip Girl star met in May 2007 at the Hollywood nightclub Hyde." This was peak 2007 in every conceivable way. TBT: Sebastian Stan and Leighton Meester Once Made Out at a Basketball Game in Front of Chace Crawford One of their reported dates (which of course took place at Marquee) included a show "provided by performers in Oompa-Loompa costumes." Famous singer and up-and-coming actor visit popular nightclub to watch ridiculous-sounding performance art — like, that is an episode of Gossip Girl. When They Peaked: Like every Very Cool And Nonchalant Hollywood Couple, Crawford and Underwood refused to actually confirm their relationship. Luckily, Crawford's Gossip Girl co-star Nicole Fiscella said what the pair would not, telling People, "They're the cutest couple." Anyway, both parties appeared (separately) on The Ellen DeGeneres Show in late 2007. During Underwood's visit in November, DeGeneres grilled the singer on whether she'd cook for the cast of Gossip Girl. "Would you cook for Chace, for instance?" she asked. Clearly on the spot, Underwood laughed and said, "I would cook for anyone that would like me to cook for them." "And would he like you to cook for him?" DeGenerous prodded. "You should call him up and ask him," Underwood told her, noting that she didn't have his number. DeGeneres then (of course) presented a paparazzi snap of the couple. "He's right next to you, you could've asked him his number right there!" she joked. TBT: Penn Badgley Called Ex-Girlfriend Blake Lively Both His Best and Worst On-Screen Kiss When Crawford visited the show a month later, DeGeneres played a similar trick on the actor. His sister, Candice Crawford, had recently been crowned Miss Missouri, and DeGeneres shared a photo of the beauty queen with the audience. The talk show host then made her movie, telling Crawford, "You know who she looks a little like is Carrie Underwood." Crawford, even less sly than Underwood, said "Really?? Who is that?" in mock surprise. "She's someone who was here on the show and there was a picture we found of you two … " DeGeneres said. Cue the same awkward sidewalk photo from Underwood's appearance. "That's not me!" Crawford joked. "What are you talking about?" When asked more explicitly whether he was dating anyone, Crawford said "I'm trying to get a pet right now … A panda bear … Maybe a flying squirrel?" The commitment is truly admirable. The Breakup: By February of 2008, Crawford and Underwood's status was unclear. When a reporter asked the Gossip Girl star about his relationship with the singer, he replied, "You're under the assumption that we're dating now." Two months later, it was official. Crawford's aforementioned sister told People that the actor was "upset about the breakup. It's always hard when you lose a relationship." Underwood addressed the split too, telling Extra that it was "completely mutual," adding, "We broke up over text so … it's like 'peace out.'" Nate Archibald would never. "It just didn't work," she continued. "We both knew it didn't work and [had] no hard feelings at all whatsoever." Of course, "sources" insisted to People that it was tad bit more complicated than Underwood had portrayed. "Carrie is the one who broke Chace's heart, not the other way around," an insider told the publication. "He flew to visit her, went on tour with her — he did everything he could for this girl." TBT: Frank Sinatra Wooed Mia Farrow By Taking Her (and Her Cat) on His Private Plane Another fly-on-the-wall said Crawford was the one to break things off: "He was upset, but he also had to make the decision that it wasn't meant to be anymore." In 2009, Crawford told People he had "nothing bad to say" about his time with Underwood. "It was awesome," he said. "I just didn't know how to deal with it. I learned a ton about dating someone in that kind of spotlight. It was such a whirlwind, but no regrets." When Underwood and former hockey player Mike Fisher got engaged later that year, Crawford told Us, "I wish her the best." In a strange turn of events, Crawford's sister ended up marrying former Dallas Cowboys quarterback Tony Romo, Underwood's ex-boyfriend. Where They Are Now: Crawford dated actress Rebecca Rittenhouse for several years before splitting in 2018. His current relationship status is unknown. Next up for the actor is season 3 of the hit Amazon Original series The Boys out later this year. Underwood wed Fisher in 2010. The couple has since welcomed two sons together: Isaiah, 6, and Jacob, 2. The singer's eighth studio album, My Savior, will be released on March 26, 2021. #TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.