Everyone knows that Walt Disney World is a wonderful place to propose to your loved one. And how could there be
a better time to receive that proposal than during Dapper Day weekend. In 2017, Adelene posted on Facebook that
she wanted to know ahead of time if anyone knew if there were any proposals coming up because, if so, she wanted
to wear waterproof mascara. Of course, that set our minds in motion. Why not stage a proposal during each day of
the events, and be sure to get them on video or at least in photos. We warned on social media that Ray often
carries “engagement rings” with him just in case. Someone responded, “Rings? Plural?” We said he always likes to
be prepared. The following photos are from various proposals done by Ray to different ladies. It is all in fun, but the
more often he did it, the more those proposals became in demand.
Addy had no idea what was coming, but here she is at Disney Springs on Dapper Day eve enjoying the evening
with a group of friends. Since she was the one who had asked about proposals, of course she had to be the
first proposal Ray did. The crowd went along with it, and there were a few passersby who weren’t in on the
story, but stopped to see the proposal happen. It caused lots of commotion, but everyone had fun with it.
You might be able to see that Ray even had a ring box in his hand with a faux engagement ring.
Marina said she has waited for over a year for her proposal. She finally received it at Dapper Day in November of 2018.
Her expression shows her response. “Finally!” It looks like Joanie might not be as willing to share him as anyone had
expected, but she is getting used to it.
Kirstie had been one of the first three original women to be
proposed to by Ray. One of the ladies said this year that they
thought there was a time limit and that they needed to have their
proposal renewed. So Kirstie and one of the others received their
second proposal during the 2018 Fall Dapper Day festivities. Kirstie
was all aglow at the thought of the pending engagement.
Once word got out that Ray had proposed to one woman, others started acting jealous, like they wanted to receive a
proposal, too. Ray did three proposals the first time, and has done a couple more since then. The first three, in order,
were Addy, Dani and Kirstie. Since the women think the proposal is only good for a limited time, he has again proposed
to Addy and Kirstie. We’ve also seen him proposing to Marina, but we think the one that is most important is the one to
Joanie. It looks like she is the one who has stolen his heart for good.
Photo by: Sean Neumayer
In the Spring of 2016 at Dapper Day, Ray decided to propose to Joanie again. He always carries
engagement rings with him in case he gets an urge to propose once more. We are wondering if this
started the trend of wanting a proposal from Ray at various events.
Ray proposed to Dani and she was very
excited about it. Then she got jealous
because her fake fiance then proposed
to Kirstie. So she said she might back
out of the engagement.
Ray found these photos of Dani online and couldn’t believe his eyes!
Here is Dani in the arms of the famous screen star Woody! The fake
engagement has been on shaky ground ever since these photos were
discovered.
The same year that Ray proposed to Dani, in the Spring of 2017 at Dapper Day in Epcot, Ray next
proposed to Kirstie. As you can see from the photo on the left, Dani was very jealous and threatened to
call off their fake engagement. Kirstie wasn’t sure how to react.