In Venice, Sept. 5. Photo by: Chris Jackson / Getty
Hello ... Goodbye| Renee Zellweger
After a brief getting-to-know-you period – largely conducted via e-mail – the couple quickly and stealthily moved to the next level, with Zellweger secretly accompanying Chesney on the road, where she often "stood alongside the stage like a little teenager, clapping for her man," says Wilson.

Chesney was equally smitten. "In all honesty, Kenny struck me as a school-boy about it," says songwriter Rodney Crowell, a Chesney friend. "He said that he felt he had a chance to put something really good together with her." Another Chesney pal notes that the singer – who had been previously engaged in 1999 – was eager to settle down. "Kenny is in love with being in love," says the friend. "He was ready to get married."

Zellweger, whose romance with rocker Jack White had ended the previous fall, was ready as well, initially playing the role of supportive new wife on the road. Though they rarely appeared in public together, those who know the pair say they spent more time with each other than people realized – at least in the beginning – and one friend estimates that she was present on his tour "about 40 to 50 percent" of the time.

Still, "they got married and spent a couple weeks together," says Wilson. "Then she was off [to promote Cinderella Man] and he was touring." The schedule was hardly ideal for establishing a firm foundation for marriage or family. Notes a Chesney pal: "This isn't a lifestyle conducive to a relationship until you are willing to put your career in the backseat."

Friends also say that Chesney was uncomfortable with the level of scrutiny involved with being married to an Oscar-winning movie star; one pal recalls a frustrated Chesney complaining that paparazzi were disturbing the waters off his St. John retreat and scaring off the fish. At the same time Chesney's more relaxed, Nashville-style approach to media relations may have caused some friction between the two.