"If I feel like I’m making headway, I’ll keep going,” Dent told the Charlottesville Daily Progress ahead of this week's Charlottesville challenger. “If not—if I’m floundering or taking steps backward—then I’ll make that decision [to retire] sooner rather than later."

Dent and his wife, former pro Jenny Hopkins Dent, are parents of a 9-month-old son, Declan. "It’s a challenge and a life change," said Dent, "but I’m having a great time with it."

The 29-year-old reached a career-high of No. 21 in 2005 and was sidelined for two years after multiple back surgeries and returned to the tour in 2008. He has been as high as No. 76 since coming back and is now ranked No. 89.

Dent added that he had moved away from his trademark serve-and-volley game upon his return and was struggling to find full comfort from the baseline. "When I came back, I said, ‘I’m going to rework my game and make it fit in with the modern style,’" he said. "That’s kind of been frustrating because I feel like I’ve been floundering with the same problem for about a year and a half."