Josh dresses as Cher for fun.
Over the years, Oprah and her team have hooked up deserving fans with college scholarships, once-in-a-lifetime opportunities and dinners with all-star athletes. And who can forget Oprah's "you get a car!" giveaway?

Oprah says she loves to make dreams come true...but it's not as easy as it looks. "My producers spend weeks and weeks planning, coordinating, plotting, scheming every little detail," she says. "Then, they sit on pins and needles hoping to pull off the ultimate surprise hookups."

When it's time for the big reveal, Oprah says you never know how someone will react. Josh, a massage therapist and Cher enthusiast from Portland, Oregon, didn't disappoint.

After learning about Josh's love for music superstar Cher—he even dresses up as her for fun—Oprah's team worked with his partner, Rob, to orchestrate a special surprise.

"I'm about to surprise him with something that is going to totally blow his mind," Rob says. "I'm about to go inside and tell him that The Oprah Show is sending us to see Cher in Las Vegas. He's going to freak out."

Watch Josh's surprised reaction to the news!Watch

When Josh gets the good news, he can barely contain his excitement. After a few happy tears, Josh packs his bags and heads to the airport with Rob.