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From a trip to Los Angeles to her new nose, a Palm Harbor woman just can't lose

Christine and Dan O’Leary recently won a three-day trip to Los Angeles for an awards show where they met actress Debra Messing, right.

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Christine and Dan O’Leary recently won a three-day trip to Los Angeles for an awards show where they met actress Debra Messing, right.

PALM HARBOR — Nearly every night for the last 14 years, Christine O'Leary has spent an hour on a single activity: entering contests.

Some might call her a contest-aholic. Or obsessed. Any way you cut it, she's a serious winner.

Among her prizes:

• A private concert with Lenny Kravitz. ("I got to sit on his lap.'')

• Plastic surgery. ("I won a nose job.")

• A trip to a Hollywood awards banquet. ("Dana Delaney was right there when we got out of the limo.'')

Among her more ordinary wins, a cruise to the Bahamas, jewelry, trips to New York City and spa treatments.

O'Leary, 38, is at a loss to explain her amazing success rate.

"I don't know why," the Palm Harbor resident said. "I'm lucky like that."

Of course, she acknowledges there's more to it than luck. "I play every day."

• • •

O'Leary's first big win came in 1995, when she entered to win the chance to propose to her boyfriend, Dan, at a Tampa Bay Storm game at the old ThunderDome in St. Petersburg.

"I actually did it as a joke," O'Leary said of her last-minute faxed entry. "I never thought I'd really win."

But win it (and a pair of wedding rings) she did. She popped the question during halftime on June 1, 1995. She and Dan were married two years later.

• • •

Contests have allowed O'Leary to experience things she never would have otherwise.

Like spending a day with ''celebreality'' D-lister Victoria Gotti, daughter of the infamous John Gotti.

"Her and I hit it off," O'Leary said. "She was so awesome."

And the Kravitz concert at an intimate club with just 40 guests.

"We got to meet him and be on the stage with him," she said. "He was so nice."

Then there was the plastic surgery. O'Leary won a $6,000 nose job from a Mix 100.7 radio contest.

"I always wanted my nose done ... so I wrote this funny story about how I didn't like my nose and stuff and they must have liked my story," she said. "That's probably the most expensive thing that I've won."

• • •

O'Leary's latest score was a January trip with Dan, 40, to Los Angeles, where they walked the red carpet at the 20th annual Producers Guild Awards, the grand prize in a sweepstakes.

She had been wrestling with a way to afford a 40th birthday celebration for Dan, a regional restaurant manager. She had even joked with Dan on New Year's Eve that she hadn't won anything all year.

A few days later, she got the call from Parade. Her name was randomly selected out of about 5,000 entrants.

"She's the luckiest girl in the world," Dan O'Leary said. "I'm waiting for the lottery right now."

The trip to Hollywood, valued at $4,900, lasted three days, but the highlight was the awards ceremony, said O'Leary, an accountant for Outback Steakhouse's corporate office in Tampa.

"The minute we get out of the limo, we were on the red carpet," O'Leary said. "It's just what you see on TV, the lights flashing, the paparazzi."

O'Leary said she chatted up actress Debra Messing ("She said she loves Tampa"), sat right behind Ron Howard ("I could have tapped him on the shoulder") and met Michael Douglas ("I almost fell on the floor!").

"Al Gore was three tables over," Dan added. "We got whiplash from looking around all night."

• • •

O'Leary doesn't waste her time dropping business cards into fishbowls for free lunches.

She's after the big one.

Worthwhile contests must meet two criteria — prizes she's not able to afford but that also are low enough in value that she'll be able to pay the taxes on them.

She scours the Internet and her favorite magazines in search of them. Then, it's all about the clicking. "I keep the ones that I have my eye on under my favorites (list). I go to the link. Hit auto fill. Done."

Essay contests also appeal to O'Leary, who loves to write. Humor is a good way to get a judge's attention, she said. Like this line from her nose job entry: "My nose is so big ... it hits the windshield when I drive."

In the end, she said, it's all about having fun.

"I'm not that serious about it," she said. "It's not like I'm obsessed.

"Some people like to knit to relieve stress. For me, this is a stress reliever. It's not that I'm sitting there thinking I'm going to win. That's just my way of chilling out at the end of the day."

Rita Farlow can be reached at (727) 445-4162 or

O'Leary's contest journal

Christine O'Leary keeps a journal from all of the trips she has won. Here are some excerpts from her trip to Hollywood, Jan. 23–25, for the 20th annual Producer's Guild Awards:

First impressions of Hollywood

"Danny was amazed that across the street (from the hotel) there was a legal medical store that sold pot. I was more interested in the doughnut shop next store."

Touring Los Angeles on a double-decker bus

"We got our tickets and sat on top of the (tour) bus and went all around Hollywood. It was chilly and breezy, but I didn't care. It was so much fun to see all the things you see on TV."

Meeting Debra Messing at the award ceremony

"She was gracious and kind to us and even posed for some pics! She was so down to earth. I couldn't believe this was even happening. Someone pinch me! When a moment like that happens to you, your brain suddenly stops functioning correctly."

The end of the evening

"I felt like I was turning back into a pumpkin and disappointed that all this excitement was coming to an end. It was one of the best nights of my life."

From a trip to Los Angeles to her new nose, a Palm Harbor woman just can't lose 02/09/09 [Last modified: Tuesday, February 10, 2009 10:15am]
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