Christine O'Leary, 38, spends an hour nearly every night searching magazines and the Internet for contests, The St. Petersburg (Fla.) Times reported Tuesday.
O'Leary, an accountant, said she never enters contests where the prizes are worth so much that she won't be able to afford to pay the taxes on them.
In the last 14 years, she's won a $6,000 nose job from a plastic surgeon, a private concert with musician Lenny Kravitz, a cruise to the Bahamas, jewelry, spa treatments, multiple trips to New York City and a walk down the red carpet last month at the Producer's Guild Awards in Los Angeles.
She even won two wedding rings and a chance to propose to her boyfriend -- now husband -- Dan, at a Tampa Bay Storm game in St. Petersburg in 1995.
"She's the luckiest girl in the world," Dan O'Leary said. "I'm waiting for the lottery right now."
Celebrity Families of 2014 [PHOTOS]