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Casandra and Chuck Memorable & Sweet Proposal
(7 Votes)

Please comment below what you liked the most and what you think is the most romantic, crazy, and funny in their story. And more important, why do you think they deserve to win the contest.

You cannot vote for this story anymore, as this story participated in constest that ended on August 31, 2011

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Casandra and Chuck Memorable & Sweet Proposal


You cannot vote for this story anymore, as this story participated in constest that ended on August 31, 2011



Quite a few years ago, they both worked for the same company - Casandra in the Cayman Islands (Caribbean) and Chuck in Toronto, Canada. After hurricane Ivan hit Grand Cayman, the office there initiated their Business Continuity Plan by transferring a few employees to the Toronto office for a few months in order to continue their work. One morning, we ran into each other in the hallway and made eye contact - or as Chuck says, fell in love at first sight (swoon!). By that afternoon, Chuck had found out who Casandra was and what she was doing there in the office. The "Cayman people", as they were called, had set up shop in one of the training rooms and were continuing business as usual while their office was being refurbished in Cayman. Chuck made it a point to stop by the room on a daily basis for "work purposes"!

During the few months working in Toronto, Chuck got to know one of Casandra's colleagues/friend but the most he got from Casandra was "Hi" (very shy). For their last night in the country, Chuck invited them both out to the bar/lounge where he works part-time...a nice send-off. Being the nice guy that he is, Chuck offered to pick them up at their hotel. Throughout the night, Casandra mostly ignored him (lol) - she was under the impression that he was interested in her friend after all (that's noble right!). However, when her friend went "missing" for an hour or so (it was planned!), Chuck got to hang out with her because some other guy was bothering her....so he got to play "protector/hero/boyfriend". By the time Casandra's friend returned, it was time to head back to the hotel to get some rest before flying back to Cayman the next day. Before they left, Chuck asked Casandra for her number so that they could keep in touch and he got it.

Over the next few years, they kept in contact by work email and cell phone every so often. During that time, they both left the company. As it turned out, on her last day at State Street, she emailed to tell him that she was going to work elsewhere, that she'd contact him once settled in and gave him her home email address....but they didn't email. Then on New Year's Eve 2008, Chuck got a text message, from a long distance number, wishing him a Happy New Year and decided to call back . Casandra answered. He asked who it was and she said "Casandra". His response was, "Casandra who?" - apparently its a popular name in his phone book (lol). Once it was cleared up she was "the Casandra from Cayman", the first question she asked him was if he was married with kids yet. He said "no" and asked if she had a boyfriend. She said "no". Being short on time since he was working, Chuck said he had to go but that he'd call her in the morning....and bright and early, he did!

From there on, the rest is pretty much history..... Casandra and Chuck spent A LOT of time on the phone/Blackberry messenger/email getting to know each other all over again. He reminded her how "mean" she was when she worked in Toronto and through this conversation it was finally revealed to her that he had always been interested in her and not her friend, like she'd thought!! (awww). A month later, February 24th to be exact, they began dating long distance and alternated visiting each other...and somewhere along the way, realized they would spend the rest of their lives loving each other. After 1.5yrs of long distance, Casandra moved to Canada & they now live together in the GTA!

The best part. was still yet to come......Upon returning home after some work with the homeless & a family function on Christmas eve, at 1:00am on Christmas morning (2010), they decided to open gifts!! They cozied up on the couch after baking muffins & making hot chocolate together, and shared their cards/gifts.... When it came to the last present from Chuck, he asked her to close her eyes and so she did. When she opened her eyes, there was a ring box in her hand & much to her shock, Chuck in front of her asking to marry him! Apparently a few weeks before, he'd asked her parents blessing (awww) and had planned an elaborate celebration with family over Christmas! (she had no clue!) She said yes of course & just about burst into tears!! He then snuck out onto their balcony where he'd hidden a chilling bottle of champagne! It was truly memorable & sweet! They are now planning an outdoor Summer wedding!


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