Tim H.
Alright...the general game plan for the engagement was developed over multiple weeks, however I can't lie, much was decided the night before. I'll start from the beginning though - going all the way back to last December. Knowing that I wanted to marry Maura, but not really feeling ready (not 'adult' enough?...I don't know), I at least formulated a rough plan that sometime in the year 2004 I would ask her to marry me. Over this past year I tried to determine what ring Maura wanted all the while acting disinterested and annoyed. Tough work, but I REALLY wanted it to be a surprise.
Around September I started actually looking for rings and the diamond. There are ALOT of different settings and diamonds out there. Maura had shared a few different ideas with me (despite my apparent disinterest/annoyance), but they were all very different from each other. I kept looking, kept studying her reaction to different diamonds and settings. In November I finally decided that it would be prudent to propose with a temporary setting, with the diamond that I knew she wanted. So, before Thanksgiving I had the diamond (mounted in a temporary platinum tiffany setting). I wore it every night, and began planning how I would ask her to marry me. Maura asked me to set aside 12/18 so that we could have our little gift exchange...as we wouldn't be together with each other for the holidays....sounds like the perfect time to do it, right? I'd get a night alone with her, and she'd never suspect anything....
Early December I started calling all of the top/romantic restaurants in Chicago for reservations....Everest, North Pond, Gejas...but unfortunately they were booked. Gejas said that if I showed up before 5pm the day of, I could put my name on the list and most likely get a table later that night. Ok...it was definitely one of my most romantic meals with her...worth the gamble. I also booked a room at the W on Lakeshore...very hip/ very romantic. I had the general game plan that after dinner I would somehow get Maura downtown and propose either along the river, or in the courtyard of the old church across from the Hancock building. I was really really hoping for snow.
Next I needed to ask Don for his blessing to marry his daughter. Monday I called Don and set up time Tuesday for lunch. I didn't think it would tip off anything, as we work right across the street from each other...and for the past 4 months had told each other we needed to have lunch. On Tuesday I met Don in his lobby, and we walked over to the Bergoff for lunch. A BBQ sandwich sounded like a good "ask for her hand in marriage" type meal. After a few minutes of conversation, I told him "Don, as much as I really appreciate this time to just hang out...I have a little business I need to take care of. You've probably expected this to happen for quite some time, but know that I'm in love with your daughter and ask you know for your blessing to marry her". Ok...it probably wasn't as smooth as that, I did feel very emotional and choked up....and very intimidated. Not necessary by Don, but by the father of the girl I wanted to marry...although Don taking his sweet time to answer "yes" didn't help me out in that regard. :) No - Don said some very sweet things about Maura and I....and told me that marriage was about respect and communication and love. He thought we sufficiently demonstrated those qualities clearly enough. He asked that I feel free to tell him anything...and that he was excited for me to join the family. With that, I hugged him (a first), and he let me finish my sandwich (which I couldn't).
Friday I knew I needed a full night to do nothing but plan for Saturday. I told Maura that I was playing poker with Focker and the boys all night, and told her to catch up on sleep. I then called in my big guns...Laura Rodriguez (aka 'LoRo'). She said she'd be over at 6:30pm, and surprise surprise wasn't over until close to 10pm. I did some research however on the Sofitel Hotel (as Maura mentioned earlier in the week how cool it was). With confirmation from Laura, I canceled the W and booked the Sofitel....'deluxe room' baby. I told her my general plans, and I showed her my "diamond box in boot" routine I was working on... She of course dug it. I later worked in the "feels like a rock in my boot" routine which was much more fun. :) Laura also gave me a few ideas on some fun places to celebrate after the engagement...something that I was struggling with.
So...Laura and I headed downtown to do a quick rehearsal of how it was to go down. In the cab she told me about a nice alternate restaurant called 'Le Colonial' at 937 N State Street. We walked in and checked it and it was perfect. They couldn't tell me if they had reservations available, but I got the number and promised to call first thing in the morning. Next we checked out the hotel and talked with them about arranging the room. Ah...the concierge can take care of flowers, champagne, candles, and chocolate covered strawberries? Excellent...that would save me alot of running around on Saturday. We then walked down Michigan Ave and after scoping out Water Tower and the old church courtyard, we both decided that the Christmas tree in front of the Hancock building was a sure thing. It was beautiful, it was in front of a prominent Chicago building, and more importantly it was in a lowered courtyard which provided a bit of shelter from the wind/cold, reduced the noise from Michigan Ave, and a bit of privacy from the hoards of people around. (Special note...Laura and I were downtown Friday night closer to midnight...and there might have only been 3 people down there). Laura and I then ended our night over a few drinks at nice wine bar around the corner. What a good friend!
Saturday morning I coordinated a few things with the hotel and finished wrapping a few Christmas presents for Maura. I was worried about my 'outdoor' activities for that night (proposal along Michigan, and horse carriage ride), and how I could ensure that Maura would dress warm enough that she could enjoy herself and not be frozen. Ah ha! I happened to come across the event "ice skating in Millennium Park" after searching Metromix. I called her and tried to sound as hung over as possible (would she think I'd be proposing after getting wrecked the night before and sporting a whopping headache!?). "Ice skating - dress warm as you can...it'll be really cold". I then ran out and got a professional haircut from a salon. For those that know me...this is HUGE. First professional haircut in 4 years! She even put "product" in my hair...I was worried that the "product" might tip Maura off that something was going down....but I thought I could play it off...which I did. :)
Clock was ticking...and I still needed to run downtown to drop off the over night bag at the hotel, as well as drop the ring box and champagne off at the restaurant. (I had originally thought of carrying the ring in the box in my boot the whole night...but the idea of ice skating kinda botched that one, ya know?)Ah ah! Didn't Focker say he was going downtown for dinner and a theater show? Whatta good friend.
I spent the last hour custom making a quick ring container out of two film case containers, shoe glue, and cotton (can you say MacGyver?), washed and dried some of the clothes/gifts that I got Maura (so she could wear them in the morning), and wrote a quick Christmas card for her to read in the morning.
And....I'm off to pick up my bride to be. I felt great. I had a solid plan...and I really knew without a doubt in my mind that it was going to be a perfect night. I had even checked the weather report before leaving and they said it might just snow tonight....wouldn't that be perfect? I called her on the way over and she told me she was in the process of 'layering'. Hahaha. As I pulled in front of Maura's apartment a few flurries fell down upon me. Big smiles. I dumped my gifts and 'over night stuff' off in her apartment, commented about how nice it will be to get in PJs later that evening and snuggle on her couch. And we were off to go ice skating. Maura was wearing blue jeans over leggings, with a nice thick white sweater....good, at least she won't be cold later in the evening. Leaving her apartment I shook my boot a bit as if I had something in there, pulled up my pants...looked in there ("look, see... nothing up my sleeves"), and continued to the cab.
We got down to Millennium Park and wouldn't you know it.....three thousand other people had the same idea we did. The line to rent skates was a least two hours long, so we opted for some hot coco (with mounds of marshmallows) and watched the ice skaters from the rink side. Maura was especially drawn to a 3-4 year old little boy zipping/weaving all over the rink. We had a wonderful time there just talking and listening to the Christmas music on the PA. After getting our sugar fix from the marshmallows with coco, we walked a few blocks and saw all of the Marshall's window displays (Snow White...very freaky dwarfs). Again...."dang, feels like a rock in my boot or something...".
Next we hopped in a cab because our 6pm dinner reservations were approaching. Maura was clearly very excited about where we were going to eat....I told the cab driver the address, and she tried guessing the restaurant. She couldn't, and I of course took advantage and mislead her into thinking it was Tavern on Rush. We jumped out of the cab near the restaurant and proceeded to walk in the direction of Tavern...conveniently walking right in front of Le Colonial. She said "Oh - I've heard of this place!", and I told her we should check out the menu to see if it looked good. Then I opened the door to the restaurant and shuttled her inside. Needless to say she was confused....and we went upstairs and I gave the guy my name for the reservation. He took us back to a very quite secluded (non-smoking) covered/enclosed balcony that overlooked Rush street. Dark, soft funky music, and candlelit...it couldn't be more perfect. Even the snow thickened up and started really coming down....right next to us. Perfect.
Even before ordering drinks Maura said that she was going to take off her leggings because they were really tight and uncomfortable. I expressed that she should probably just leave them on (thinking of my plans later that night), and she did anyway....tying them around her waste. Hahaha. We ordered some cocktails followed by an excellent bottle of wine, and delicious appetizers (shrimp on sugar cane, BBQ ribs, and diced Monk Fish and vegetables). I then excused myself to the bathroom and immediately went to the manager to get the ring box Ryan had dropped off earlier. He was very excited because he assumed I was proposing in the restaurant (as did all of the staff that he told....sorry to disappoint you buddy). In the bathroom I took the ring from my custom film case capsule and put it into the box...and then into my boot. On the way back to the table I told our waitress that at the end of the meal I would point to a desert item and asked for it packaged to go....and to not actually wrap the desert, but instead the two mini bottles of champagne that Ryan had dropped off. The rest of the meal was heavenly - everything was perfect. For an entre we shared jumbo shrimp with asparagus and garlic (our favorite) with a spicy chili sauce. For desert we had a banana chocolate wonton, with a delicious Moscoto desert wine. With the champagne concealed in a to-go box/bag, we left for "home".
Before going home, I told Maura that I wanted to see the lights along Michigan Ave, and that we could catch a cab home from there. On the way of course I played again on the 'rock in the boot', shaking my boot every now and acting annoyed. On Michigan we immediately walked through the old church courtyard I had considered before. I'm sure if Maura had suspected anything...her suspicions died after we left the romantic courtyard of the church. :) Muhhahahaha. :) I suggested that we then catch a cab on the other side of the street in front of the Hancock because it was the direction we were heading. On the other side of the street the large brightly lit Christmas tree in front of the Hancock building called to us. "Oh, what a beautiful tree....lets go down and take a quick picture before we go back home". As we walked down the steps into the courtyard, my pulse quickened. It is doing it now as I write this...something about seeing the spot you are going to propose....occupied by another couple looking like they are proposing??!?!?! OH SHIT!!!! I stalled and stalled. No way could I propose back to back...especially if Maura saw it happen. I tried distracting her with pictures, and thankfully finally the couple moved on (just taking pictures). Whew! I literally double stepped it over there with Maura - really fearing/worried that another couple was going to jump up there and propose before I could. I didn't really pay much attention to the fact that there were many people in the courtyard (unlike the night before). There was a group of people taking a photo in front of the tree when we got down there...guess we'd have to wait our turn. Heck, might as well get a shot as well. I asked the same guy to take a picture of Maura and I, which he did. I then handed the camera to Maura and asked her to take a photo of me next to the tree. I walked over to the tree and kneeled down. "Hold on....let me see if I can finally get this rock out of my boot." On knee, facing Maura, with snow falling down on and around us..."Maura...I think I finally found that rock". I then slowly pulled the ring box out and held it out for her to see. I could tell she was confused at first....didn't know what the heck it was....and I guess in her defense the box was very dark, and perhaps she was expecting a light blue box or something (gulp). Then her face changed and her jaw dropped. I asked to come a little closer....and she shuffled an inch at a time closer to me. I then opened the box and said (sensing that she was overwhelmed enough) "Maura, will you marry me?"...the phrase "ohmagod, ohmagod, ohmagod" came out of her mouth a hundred times and at least she came close enough to me I could take her hand and put the ring on her finger. I then stood, hugged her, and asked her again...this time an audible 'yes' came out mixed between the 'ohmagod's. We then kissed and the small crowd that had gathered around applauded with "congratulations". We kissed again, and I thought it was time to move along...not wanting to be quite the spectacle...but Maura said she couldn't...that she couldn't even move her legs. I hugged and kissed her some more, and then supporting much of her weight walked her towards the stairs to leave the courtyard. Along the way many other couples offered their congratulations, including a young family with their baby stroller. Very special.
We then walked over to the water tower where I had planned for us to jump into a horse carriage and be whisked away....but whatta you know....a line of 50 people. I suggested that we head off somewhere warmer (as the snow was still falling on us) to celebrate, but Maura liked my idea, and wanted some time to settle down a bit and grasp what happened.
Our horse carriage arrived, Maura and I piled in, and a nice man took a Polaroid of us. Fortunately there were heavy blankets which we quickly warmed up under. I suggested that perhaps Maura might have yet another 'gift' in the to-go bag, which she replied 'impossible'. Hahaha. I reached in and pulled out the two gift wrapped champagne bottles and in true good class, toasted each other and drank from the mini bottles. :) The carriage ride was spectacular...taking us through much of the city and along inner lake shore drive...all the while with white snow dropping all around us. Our horse had sleigh bells on as well....so the jingle enhanced the magic all the more.
Ah...what next? Guess its time to go back to Maura's apartment? I convinced her that it was early and we still had time for another quick champagne toast in the city before returning home. We walked a couple of blocks and arrived at the Sofitel Hotel bar. The bar was crowded, and my plan really broke down at that point...so I flatly told her that as a final surprise I had reserved a room for the night. I left her looking through the hotel gift shop as I ran upstairs and lit the room's candles. I went back the lobby and then escorted her to the room...on the top floor of the fabulous hotel. We opened the door to our room and with the lights dim, the candles flickering, and the rose petals ALL OVER the room - it was incredibly romantic. I walked her over to the closed windows, and with her right beside me I opened the curtains to reveal an amazing view of the city, the lake, and most predominantly the Hancock and the lighted Christmas tree that we became engaged under.
Tim Holland
