1 of 9
STAND BY HER MAN
As soon as Jessica Simpson and Dallas Cowboys quarterback Tony Romo were linked in Nov. 2007, the singer became a fixture at his games. Though she wasn't always a welcome presence by fans, Simpson (here cheering on her guy at a Dec. 16, 2007 game) took it in stride. "I really think it's because I was wearing a pink No. 9 jersey and not a blue one," she later joked about being called a jinx.
2 of 9
IT'S A DOUBLE DATE!
Just before their first Valentine's Day together, Simpson and Romo joined Ashlee Simpson-Wentz and her then-boyfriend Pete Wentz for a double date at Dallas's Grand Lux Café on Feb. 13, 2008. The next night, the couple kept to themselves, marking the holiday with a romantic meal at Nove Italiano restaurant. "All eyes were on them," an insider said at the time.
3 of 9
When Romo wasn't busy on the gridiron, the football star and Simpson would often check out other sporting events. On March 18, 2008, the two put on silly faces as they cheered on the hometown Mavericks courtside at the American Airlines Center in Dallas.
4 of 9
IN HER FACE!
Simpson helped her beau have a finger-licking good birthday celebration on April 19, 2008 in Dallas. The singer and Romo shared cake – they both fed each other! – during his 28th birthday bash at the nightclub Suite. She even took to the mic to sing "Happy Birthday" to Romo, then "licked cake from his face as everyone cheered them on," a club insider said.
5 of 9
Despite reports of a split, Romo was a doting date to Simpson at little sis Ashlee's wedding to Pete Wentz on May 17, 2008. "They were cute," the bride said of her maid of honor, who dirty-danced with Romo at the Alice in Wonderland-themed reception.
6 of 9
MAKING A STATEMENT
7 of 9
A week after meeting Romo's parents, Simpson had plenty to smile about as she celebrated her 28th birthday at Sagebrush Cantina in Calabasas, Calif., on July 9, 2008. The couple dined with Ashlee and Pete before partying at West Hollywood's Key Club, where Romo serenaded the b-day girl with Journey's "Don't Stop Believin'".
8 of 9
MORE TO LOVE
While making headlines (and even a cover of PEOPLE) for her recent weight gain, Simpson and Romo (on Feb. 13, 2009) celebrated this past Valentine's Day at New York City hot spot Waverly Inn and capped off the night with dessert at Serendipity. Simpson, who played a show in the Big Apple the day before, told the crowd at the time: "There is something about being in love, right? It just makes you appreciate every day, right?"
9 of 9
Just a week before their split, Simpson showed her support by joining Romo at the 2009 ATampT National golf tournament in Bethesda, Md. The football star teed off alongside Tiger Woods while Simpson sang the national anthem at the kickoff ceremony. But despite their break-up the night before her 29th birthday, Simpson seems to remain hopeful about love. "Everyone needs to know that hope floats ... grab the strings and pull it back to you," she wrote on her Twitter page