Originally posted on justinwinget.com 6/14/09
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Have the pleasure of sharing the good news that Mandy and I got engaged on Friday night! It has been such an amazing weekend and were both on cloud 9…the smiles haven’t left our faces since!
Because I know that while many of you guys were there at the W to celebrate with us, some of you were not – so wanted to fill everyone in on the details…
It all started a few months ago when I really started to put some thought into how I wanted to do “this”…talk about an overwhelming feeling – but I always thrive with a blank canvas! So I had her birthday weekend circled on my calendar for a variety of reasons – the first being that I knew her family was coming to town from Cleveland to celebrate, and secondly because I knew she’d been long dreading turning 32 – so what better way to make the transition to 32 a little easier!
First I talked to our good friend Sarah about it while we were out and about Chicago for work one day, and next thing I knew, she had me in Tiffany’s looking at $50-75K rings to get a “feel for the style I wanted.” I knew she was the perfect person to talk to, as she not only introduced us and can take co-credit for us being together, but had recently been through a wedding herself…What I wasn’t sure about though was that I’d ever be walking through the doors of Tiffany’s again!
The next step (fittingly with a little nudge from the “Ding!” I get daily from Southwest) was to book a flight to Cleveland to take her dad to lunch and ask for her hand in marriage. I had been thinking about it and all the details I’d need to take care of, but hadn’t really put much footing in place yet….So that morning of April 23rd, the “Ding!” popped up with a pretty cheap fare to Cleveland, and me taking that as both a sign that I needed to do this, and also being a sucker for a good deal, I had officially taken my first big step. In my mind, there was not turning back from there…
As I had a little time before my May 27th trip to Cleveland, it was now time to start the overwhelming process of ring shopping…For those of you who’ve done it, I’m sure you can attest that the whole system is not made for the male species….It’s a complex equation of color, size, and clarity which simply doesn’t make much logical sense (demonstrated by the fact that the best colored diamond is labeled with a “D”.) So a couple hours of research & a few conversations with my mom, I was finally starting to get it all figured out…Mandy had “hinted” in the past that she would like a Princess Cut diamond with a platinum or white gold band…but I still figured I needed to get verification from her best friend Megan, whom she had surely been planning her dream wedding with since kindergarten…
So Megan and I had a great incognito lunch at Rosebud here in Chicago on May 7th where I showed up with both ideas for the engagement (which I’d need her help with) and a stack of printouts with some rings I had shortlisted. It turned out to be a great call, as she not only affirmed my hunches about ring styles, but also set me up with her aunt who just happens to be a jeweler in Cleveland…So I now had 2 reasons to be in Cleveland on Wed. May 27th…
I then had a little time to let it all soak in – literally. Mandy and I headed to Aruba, so I got to formulate “my plan” while sitting by the pool basking under the sun for 7 says. However, before I left, I sent some of my ring ideas to Jan (Megan’s Aunt) so she would be prepared for my trip there. I also blocked out that morning on my mom’s calendar to meet me up there and provide both her great insight and the moral support that only a mom can give…
As it turned out, my little day-trip to Cleveland just happened to follow up a Memorial day whirl-wind tour of Ohio which had already had me in Toledo, Dayton, and Cincinnati – so by the end of the week, I pretty much had the whole state covered! Luckily I have the best boss in the world (who I should mention can also take credit for setting us up!) and she not only let me skip out of work for the day, but gave me a ton of moral support and also set me up with a 6AM conversation the morning of with her husband Peter who had done the very same trip to Cleveland some years back to ask her her hand…Needless to say, he could relate and offered up some great advice! I should also mention that it was also a bogus forwarded email from Alison to me that had Mandy convinced that I was going to Cleveland as part of the Cavs new business pitch rather than to take care of this personal business…
The 2 hours I would spend in the air that day also turned out to be a great time to finish up my book “32 Amazing Memories” which would be the lynchpin to the “plan” that I had now started piecing together. More about that shortly – but I had a printing deadline, and this thing needed to get out!
So I arrive in Cleveland to the warm smile of a proud mother. She had some time to kill while waiting, so she struck up a conversation with the information desk attendant – I only know this because after I greeted her, the attendant told me how good of a son I was with a big smile…
Next thing you know, we were in Downtown Cleveland staring at a selection of rings at Abe, Harry, and Son and on the verge of making one of the most important purchases of my life…It didn’t take much time though, because as soon as the ring was pulled out, I knew it was the one! An hour later after sorting through some diamonds, and I had just made the littlest BIG purchase of my life!
So next it was on to Lakewood for a lunch-date with her wonderful father Ron at one of his favorite bars, the Drink. I knew it was the perfect place for the occasion, as it is great local dive with good food, cold beer, and a stairway that leads downstairs to the “restroom” – which is little more than a urinal attached to a door-less wall. I told him I was in town for work and had a little time to grab a bite, but think he was onto me..ok I knew he was onto me when he later told me that his wife Simona was expecting a call with “the details” RIGHT AFTER we were done with lunch. In typical Ron Watt fashion, I couldn’t get in a word edge-wise – so finally after 30 or 40 minutes of BS’ing about this and that, I finally cut in and did what I needed to do…and I couldn’t have gotten a warmer, more sincere response of approval. We both welled up a little bit, had a few more beers, and I filled him in on his oh so important “role” in a couple weeks. I ended my trip with another drink of the patio of their home in Lakewood and phone conversations with Mandy’s mom Simona and Brother Ronnie – both of whom were esctatic (Simona to the point of almost passing out at work, and Ronnie appropriately to the point of sarcasm.) So that was a pretty amazing day, and I was headed back to chicago a very happy man…
All that was left was to get a few details finalized and make sure that some of our friends and family would be there to help us celebrate the occasion…It was quite the elaborate plan, but I knew that with the help of all my great accomplices, that I could pull it off…
So the morning of Friday May 12th, I had conveniently made plans to drive Mandy to work so that I would be able to pick her family up from Union Station around 3:00, as she wasn’t able to do it because of some work conflicts. That turned out to be perfect, as I rarely get the car during the day and would need it to help with preparations. So after a company update meeting and a few pressing things in the morning at work, I left to start getting my propping for the room at the W where it would all go down.
About the same time, Megan, whom we were supposed to be staying with for the weekend because all 5 of us would be a squeeze in our place, was baited to send Mandy an email saying that her son had come down with Pink eye. Her story was that because they had both extra hotel points, and it was Mandy’s b-day, she was putting us up in a room at the swanky W hotel since we wouldn’t be able to stay there in fear of catching PinkEye…Of course Mandy fought it, but eventually gave in – and given the nature of her responses to Megan’s emails, it was clear she didn’t sense a thing. Things were already starting to fall into place…
First it was a stop at our fav bakery Sweet Mandy B’s for the cupcakes, then to 3 or 4 stores before I found those number candles to top the cupcakes with “32″ and to find the perfect wrapping paper for the book. Next to the flower shop to get 32 roses (which I actually had to get 36 because their sold in dozens) and then to find a vase big enough to hold them all…One last stop at Manny’s Deli for an awesome Corned beef sandwich, and it was just about time to get her fam – who had been on an anxious 7 hour ride on the MegaBus from Cleveland….
So I picked them up, got them settled into our place with some drinks (Simona still swears she didn’t polish off the majority of that bottle of wine by herself, but I’m here to tell you she did…) and I was off to the W to check in, get things set-up, then swing across town and pick up Mandy from work. The room was absolutely perfect – looking high overtop Navy Pier and Lake Michigan – and I spend about an hour getting things just right….The roses perfectly set in their vase, a good hiding spot for the ring, getting the cupcakes, candles, and book in place – and then a duh moment for me. Those 4 extra roses I had (and almost threw away) could be de-petaled and spread out over the bed…and I may have done a dry-run once or twice there in the room just for good measure 
So left the hotel around 5:30, got Mandy at 6′ish, and then it was onto what would be the quickest dinner in Watt family history at Market in the West Loop. We had a dinner reservation for 8, and were out of there just shortly after 9:00 in order to stick to schedule – un-benounced to Mandy. A little peeved that she was rushed through dinner, didn’t get to finish her glass of wine or order a dessert for her birthday dinner because everyone was “just too tired” – we then headed back to our place, got the fam “tucked-in” for the night, and quickly jetted off for the W. Little did Mandy know that Megan and Shane were following just a few minutes behind us ready to pick up her parents and Ronnie and take them to the W to meet up with us after it happened.
At the beginning of the 5 minute drive, I tried to hide my vervous-ness by playfully singing along to the top 40 tunes on the radio, but after a minute, I realized I was so off that I might be better off just keeping quiet rather than tip my hand accidentally tipping my hand that something was up….The next part of the plan is the one that had me a little nervous, as I had yet to come up with a good idea for how I could “re-check in” without actually doing it. So the only thing I could come up with was to pull up to the front door and jump out of the car telling her “you valet the car and I’ll check-in” as quickly as I could possible escape….A couple paces in circles inside the lobby of the hotel, a quick email to the troops parked at a bar near-by that the coast was clear, and a reach into my pocket for the keys, and I was back outside. It wasn’t the best scripted part of the plan, but it worked…
Before I knew it, we were up to room 2004 and on the verge of one of the biggest moments of our lives….She joyfully popped open the door to the sight of 32 roses, the cupcakes, candles, rose petals, and a mysterious wrapped present. I lit the candles and did a horrible rendition of “happy birthday” while she began un-wrapping the book..So she started flipping through the book, which contained 32 amazing memories accompanied by pictures and little snipets from our couple years together…and as it neared the end, she started to flip faster and faster, apparently sensing what was about to happen. Then there is was, page 32, and I found myself on one knee asking the girl of my dreams for her hand in marriage…it was truly an amazing intimate moment like no other.
That was of course followed by the requisite tears of joy, calls to our parents, and state of dis-belief. I had months to prepare my nerves for the whole thing, but for Mandy, who was really blindsided by the whole thing in a matter of minutes, found herself on cloud 9 and emotions you would only expect from someone who had been waiting for 32 years for a moment like that…
The last big surprise was that I had made plans for a lot of our good friends here in Chicago, in addition to her fam, to be waiting for us up at the 32nd floor sky bar at the W to celebrate the occasion and party it up! Needless to say, seeing all the people who are so near and dear to us up there to join us really capped off the perfect evening and kicked-off what promises to be an amazing year(’ish) full of celebrations and a lifetime of happiness together…So for all of you who were there, THANK YOU for being there and part of such a special evening, and for those of you who were not, we look forward to celebrating with you guys in the near future!
Cheers!
Justin
(Check out some pictures from the night by clicking here)