After orchestrating a romantic weekend as elaborate as any leg of The Amazing Race, Cheyne Whitney, 23, who won the 15th season last December with his longtime girlfriend Meghan Rickey, 24, popped the question near their home base of San Diego on Sunday.
“Other than ‘what are you going to do with the $1 million,’ the question that comes up the most is, ‘when are you guys going to get married?'” Whitney tells PEOPLE. “And I’ve been planning this since the Race ended, so I’ve been like, ‘I’m working on it! I’m working on it!'”
The Plan: It all started after their Amazing Race win when “I fake-proposed to Meghan on Jimmy Fallon,” Whitney says. “Brides magazine thought that I really did propose, so they emailed us the day later and asked if Meghan would like to pose for a wedding dress? I kind of intervened and said, ‘Hey, would you like to work on the proposal? I have some ideas!’ And they were super-helpful. I really did plan it since Dec. 10. For two-and-a-half months I have been planning this day!”
On Friday, Feb. 26, Whitney shopped at his local Robbins Brothers store in San Diego and picked out an ArtCarved 2010 Limited Edition platinum engagement ring with a princess cut diamond and diamond side stones. “I did show her best friend the ring,” Whitney says, “and she said she loved it and that Meghan would love it, so that was reassuring.”
Then on Sunday, Feb. 28, after a romantic weekend where they stayed in the presidential suite at the Omni San Diego, the whirlwind proposal would happen.
The Big Day: “We stayed downtown together,” Whitney says, “and Sunday we went on a helicopter ride off the coast, had lunch at a winery, went home and then did a walk down memory lane. We went to the elementary school we met at, the middle school we always used to hang out at, the high school we became really good friends at, and then went to this little lookout point where we’ve been going since we started dating.”
At the lookout point, Whitney handed Rickey a copy of the April issue of Brides. “He told me he had some rings to show me in the magazine,” Rickey says, “and I was like, ‘Okay, that’s kind of weird,’ and he opened up the page and I saw my name first at the top and was like, ‘What the heck?’ And saw our picture at the bottom, and I just read it and I could not believe it.”
The words read, “Meghan, will you marry me?”
“I was shocked,” Rickey admits. “I was kind of confused at first, like, I just didn’t know what was going on but once it hit me, I was in tears, and I was totally overwhelmed and shocked! It felt like I had won The Amazing Race!”
Says Whitney, “I kind of handed her the magazine, and she was taking it in and I pulled out the ring at the moment and got down on my knee, and I think it kind of sunk in for her right then. I opened up the box and I just told her that I’ve known since we started dating that she was the one.”
For a final surprise, Whitney had a crew from Entertainment Tonight come out from the bushes to capture the happy engagement. “There were cameras hiding and it was all crazy,” Rickey says with a laugh. “I didn’t realize Cheyne had done all that work to make this happen.”
Although they don’t plan to tie the knot soon, Rickey jokes, “I always tease Cheyne because I’m the planner in this relationship and I’ve been very impressed by his planning abilities, and he may be doing more of the wedding planning!” –Cynthia Wang
Tell us: For a couple that’s been around the world a lot, where should they honeymoon?Robert Benson/WireImage