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Pleasantville Resident Wins Close to $50K on 'Wheel of Fortune'

Robyn Cucurullo O'Brien shares her plans for her winnings and when she plans to take that vacation.

"You stumble during the opening interviews, you call a letter that’s already been called, then you leave a letter out when you solve a puzzle and then you’re the big winner! Perfect!"

Host Pat Sajak joked about the "winning formula" Pleasantville's Robyn Cucurullo O'Brien used to win almost $50,000 in cash and prizes on Wheel of Fortune Thursday.

O'Brien, who grew up in Briarcliff Manor and spent "a lot of time in Pleasantville," admits "the first half of the show was a little rough," but she did manage to give her now home village of Pleasantville a shout out during her opening appearance on the ABC game show—noting its status as the second best smelling place in the world.

"Pat seemed to really get a kick out of it and used it to riff off of for a bit!" O'Brien wrote in an email to Patch.

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O'Brien, who currently works for the New York City-based The Actors Fund, said she has been a fan of the show "since I was a kid dreaming of acutally being on" and spent a lot of time practicing for her appearance.

Despite her slip-ups ("I just got so overwhelmed and distracted!" she said), a personal pep talk from Sajak during a commercial break put O'Brien back on track.

"...for some reason, he just took to me and his words really helped me get out of my own way and make a comeback," said O'Brien.

And she didn't come back in a small way heading into the third puzzle.

"My strategy for the prize puzzle is always solve as quickly as you can—don't worry about banking more money because you will get a trip which the value of will add to your grand total," explained O'Brien. "So while I was down and out, during the commercial break, Pat came up to me once again and said, 'Just go out there and win the prize puzzle,' to which I replied 'OK Pat!! I'll do that!' And sure enough I did! And once I solved the puzzle 'Riding The Perfect Wave' I KNEW I was going somewhere tropical and amazing."

And the Hawaiian vacation, which O'Brien said she and her husband Jerry are tentatively planning for the end of summer, turned out to be the perfect location for the married couple of one year.

"I was beyond thrilled because my husband and I were going to go to Hawaii for our honeymoon, but opted to save a little money and do Bermuda instead," she explained. "I guess it was just meant to be and that the universe was telling us to hold off as we'll get our opportunity soon enough!"

In addition to winning the prize puzzle, O'Brien brought in enough cash to win the whole game and head to the bonus round.

"...the stage manager brought us down to the stage and told us that she doesn't know this but she drew the $35K card, and that if she gets it he's going to say 'Go' and we're going to run on stage and hug her," Robyn's husband Jerry shared. "Once that happened I just KNEW that in moments I would be on stage celebrating with her."

And O'Brien managed to solve for the word "Chalkboard" within the designated 10 seconds, making her total win in cash and prizes for the day $48,480.

"You can't imagine the shock you feel when it hits you that you've won the whole game—I was freaking out!" she said.

The win was as equally thrilling for Jerry.

"I was relieved and completely overcome by the whole situation, and in addition to being thrilled that my wife won all of these amazing prizes, I was just so happy that her big moment turned out to be even more than anything we had even imagined!" he said.

The prize money O'Brien won from the show will be used to put a down payment on a house or a condo, hopefully in Pleasantville, she shared.

"Obviously we hope to stay in Pleasantville, and if not, somewhere nearby, so fingers crossed that we find something fabulous!" said O'Brien. "I think once the check comes I may also treat myself to a little something, but pretty much every penny of my winnings is going towards a down payment."

From the friendliness of Sajak and Vanna White ("During our rehearsal, Vanna came out to welcome us all, say hello and wish us all luck, which I thought was so courteous"), to the exciting win, "the best part was every part," O'Brien reflected.

"From start to finish, everything was just beyond incredible—everything I had dreamed it would be and much much more."

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