A Look Back At Jessica Simpson's Steamy First Date With Tony Romo

Couples like Hailee Steinfeld and Josh Allen and Taylor Swift and Travis Kelce might be making modern headlines for their cross-genre romances, but Jessica Simpson and Tony Romo were one of the earliest incarnations of the music star and football player celebrity pairings. While they definitely had a tumultuous romance, the two had a steamy start to their late 2000s relationship, with Simpson sharing the details of their first date in a 2008 interview.

"The fact that this guy, on our first date, in the first 10 minutes of dinner, wanted to lean over the table and say, This is my girl and I want to kiss her — our first kiss in front of everybody — was awesome," the "With You" singer told Glamour, comparing Romo to other men she'd dated who were interested in keeping things more private.

If you're unfamiliar, Romo served as the quarterback of the Dallas Cowboys for 14 seasons from 2003 to 2016. Meanwhile, Simpson is a pop country singer known for hit songs such as "I Want To Love You Forever" and "Irresistible." She's similarly recognized for her early 2000s reality show "Newlyweds: Nick & Jessica" along with notable acting credits in movies such as "The Dukes of Hazzard" and "Employee of the Month."

When talking about the details of her relationship in an interview with Glamour, Jessica Simpson opened up about how she met her then-boyfriend, Tony Romo. Turns out, the two connected after he shared in an interview that she was his celebrity crush. A mutual friend introduced her dad, Joe Simpson, to Romo and he eventually passed on her contact information.

"Then he e-mailed me, and we flirted over e-mail and on the phone," Simpson explained. "We got to know each other by talking, which I think is the best way. We set up our first date on November 20." Romo flew the Simpson family out to Texas for the Thanksgiving Day football game, with the two setting the plans for their in-person meeting. Simpson added, "I had butterflies that you would not imagine. I wanted to puke in the cup holder."

Before meeting up at the hotel, the pop star confided her nerves to Romo over the phone. "And he told me then, '[Let's] just stay on the phone. Right when we see each other, we'll lock eyes and then hang up.' So that's what we did." At the hotel, the two shared their first date together, sealing the deal with a steamy first kiss.

Jessica Simpson and Tony Romo kicked off their relationship with an unexpected smooch during their first date back in 2007. The Texas native explained that they'd been sitting in the hotel restaurant when Romo started to lean in. "I go, 'What are you doing?' He goes, 'Nothing,' and starts pouting," Simpson recounted. "I said, 'Were you just trying to kiss me in front of all these people?' He goes, 'Maybe.'"

While Simpson may have been surprised, she wasn't at all offended by the attempted kiss. "Then I was like, 'Do it again.' He said no. I was like, 'Fine, I will,'" the pop star explained, deciding to take the kiss into her own hands. "Yeah. I'm a go-getter." Simpson later attended Romo's football game on Thanksgiving Day, with the Irish Examiner reporting that they spent the following Friday with her family.

It wasn't until a December game, in which the Dallas Cowboys played against the Philadelphia Eagles, that Simpson was pictured wearing a pink Jersey in a luxury box. Due to Romo's poor performance, that particular game sparked a lot of speculation about the singer either being "bad luck" or an unnecessary distraction. Unfortunately, such rhetoric became a mainstay of the iconic couple's short-lived relationship.