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A little help w/Chicago Proposal on V-day, please...

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wally

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Hello All -

I''m writing to ask for a little assistance. My gf is currently living in Chicago and I have plans to propose to her on on Valentine''s day. The main trouble I have with this is that while we have dated for quite some time, I''ve only been to CHI about 8-10 times for weekend visits and we really haven''t established ''our special places'' in that city. So, I''ve read LOTS of posts from Chicagoins (sp?) on this site and was hoping you could read over this plan and give me some help with the details.

My gf and I have [unfortunately] failed to spend V-day and other special occasions together over the past few years of dating. It''s usually just logistics and this year is the same - we will be spending the previous week together skiing in CO and therefor it didn''t make sense to make another trip, especially on a Tuesday.

So, my plan is to fly into CHI and surprise her at her office. My thought is that I will call her early in the day and ''fib'' with some sort of story about a flower shop mix-up and promise her that I''ll do my best to get flowers delivered, but let her know that I haven''t forgotten about her. My plan is to ''hand-deliver'' the flowers to her at her office around 3:45, dressed in a suit. With the help of her office-mates, I''ll talk her into heading out of her office and I''ll surprise her by having a towncar/limo waiting downstairs. We''ll head to her apt. for her to quickly change clothes (she dresses casual at the office) and then we''ll head to Pop''s Champagne bar for a glass of champagne (neither of us have even been there, but she often said she thinks it sounds cool, and from what I''ve read online, I concur - opinions would be appreciated!). My thought would be that we would ideally have a small table and spend 30-45 minutes enjoying each other''s company.

The next part is where I really need help. She has always said that when I pop "the big question", she''d like it to be early in the ''date'', so that we can ''revel in the moment'' as opposed to having a day filled with suspense. I have no doubt that making a surprise visit to CHI in a suit will be a pretty good tip-off that the big question is looming! I''d like to go somewhere semi-private (or completely private) to propose, but I don''t know where the best place is. Of all the different places I''ve read about, I am leaning towards either the Lily Pond or somewhere near the zoo(the fountain?). Because this is happening 2/14, I''m somewhat concerned that weather will not cooperate, so I''d really like to hear ideas on places that might be better. I looked into the indoor gardens, but unfortunately they close at 5:00 PM.

The next part of the evening is dinner. I have reservations at Chicago Chop House, but I''m not convinced that''s the best spot. I called to get reservations a few weeks back and was wait-listed at my first two choices: North Pod and Geha''s. I picked the Chop House because she has told me numerous time she really wants to take me to the ''Chop House''. Of course, I have since learned that there are lots of ''Chop Houses'' and I''m not 100% sure this is the one to which she''s referring. So, if anyone can provide feedback on this restaurant, I''d really appreciate it!

I''d love to hear feedback from people who live in CHI, specifically:
1) The idea of renting the towncar/limo - She doesn''t own a car and, regardless, we''ll be having a few drinks, so driving isn''t an option. I''m not necessarily a flashy big-money guy, but this is a once-in-a-lifetime night, so the idea of hailing cabs isn''t all that appealing. I was planning to just have the limo drop us off at dinner and then we''d get a cab home in order to save a few hundred dollars. Does anyone have any better ideas on transportation?
2) What about the idea of popping the questions at Pop''s? Like I said, I''ve never been there, so I don''t know how ''question friendly'' it is. I do plan on dropping to one knee and don''t really want an audience, so do they have semi-private booths or will my actions be a spectacle?
3) Does anyone know of not-so-popular high-rise bars that might be a good place to propose? Obviously the Sear''s Tower and Hancock building have their lounges up top, but I''m fearful that we might have to stand in a ''proposal line'' and I''d like for this moment to seem special and not have some guy 15 feet away doing the same thing. Are there other bars overlooking the lake/city that you might recommend? What about bars/lounges with private rooms/booths?
4) What about other dinner ideas? I suspect I''m probably too late for any of the popular places and I''m still hoping that North Pond will open up, but does anyone have any feedback on the Chicago Chop House or alternative, lesser known places to recommend?

Wow, sorry for the ridiculously long post, but I''d really like some help and I don''t want to ask our friends in CHI for fear of them tipping her off!

thanks in advance - wally.
 

monarch64

Super_Ideal_Rock
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Hi Wally! My husband proposed to me in Chicago...it ended up taking place at North Avenue Beach, though. On Dec. 14, 2002 (yes, it was COLD). It was a Saturday evening, and we ate dinner at Hugo Frog''s (couldn''t get reservations at Gibson''s or Morton''s--it was very last-minute on his part because he''d purchased my ring just the day before and it was burning a hole in his pocket!) After dinner, his plan was to take me to the Signature Room lounge and propose there at a cocktail table overlooking the city, but wouldn''t you know, there was a big ol'' line for the elevator itself to get up there!!! We ended up hailing a cab and went to the beach where we had spent our first sunrise together the night we met. It was perfect, and I couldn''t imagine a more perfect setting for our engagement to begin.

My point in telling you my story is make sure to have a plan B, and C if necessary.

OK, you said you would be wearing a suit, so I''m guessing you want to stick to a more formal place. Bear with me while I throw a few ideas your way...

Have you considered proposing during a carriage ride? If the weather isn''t cooperating, that might be the best of both worlds--you''re sheltered, yet you can enjoy views of the city from the ground...

ooo, I know who has a great lounge/view of the city (not totally high rise, but good nonetheless)--the Hyatt on Wacker! Check out their website.

Also, check out other hotels on the Mag Mile...I can''t recommend any specific one, but I''m sure there has to be one with a nice lounge with a good view!

Oh, oh the car...we live 13 miles west of the city, but we use a guy with a beautiful Mercedes to take us to dinner when we want to have a "fancy" night out, or to get back and forth from the city...he''s based out of our suburb, but I''m sure it would be no prob for him to accomodate your needs if you call him far enough in advance. Otherwise, go to one of those online yellow pages sites and make some calls. We usually pay him around $75 one way, if that tells you anything.

I hope at least some of my input helps you a little. My DH just walked in the door from out of town, so I will pick his brain (he lived downtown for five years and grew up around where we are now) to see if he has any more specific suggestions as far as restaurants/lounges, etc.

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flutterby

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The chop house, is the chop house. Nice place, classic Chicago steak house. Really nice, really upscale not sure how overly romantic it is though.... at least you know she likes it.

Save your money on a limo and put it towards the restaurant. Its chicago, parking and valet is a pain, and a limo just seems like a waste. Cabs are definately not a bad option, really. I''d rather put the money for a nice bottle of wine.

Sorry to say, North Pond will not open up. As a restaurant manager, it is highly unlikely someone will call to cancel and if they do, the restaurant will probably save the tables for locals.

you might want to check out vivo, its one of my faves! mention you are proposing when you make the reservation. Meritage wine bar is romantic and wont be crazy busy as they wont take too many reservations, the food there is beautiful and one of my friends got engaged there.

There are other really good options. this restaurant just opened http://metromix.chicagotribune.com/dining/mmx-060126-il-mulino-chicago,0,1540758.story?coll=mmx-dining_top_heds. It is supposed to be amazing. Nomi in the park hyatt is really nice and Avenues in the Peninisula. The wine bar in the peninsula is exceptional. It is where jennifer anniston and vince vaughn hung out all summer. Rosebud on rush is popular but really cute atmosphere.

Pops is cute, but it will be packed. Its valentines day, everyone will be out and trying to do romantic things. and champagne is it these days. I think if she wants a proposal at the beginning of the night, do it right after she gets ready for dinner, before you head out.

this was alot of rambling. hope it helped!
 

monarch64

Super_Ideal_Rock
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Hee hee, I was hoping another native would shop up...where''ve you been, Ms. Flutter? Pebbles and I were just PM''ing the other day in hopes we could get some Chicago area peeps together!
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wally

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Wow, thank you both for your valuable replies! I have already discovered that, even though I called for reservations a month before V-day, Plans A, B and C weren''t feasible.

I appreciate the feedback regarding the limo. She''s very down-to-earth (as am I) and taking a cab is probably the smartest, and definitely more economically responsible, thing to do. At the same time, I want to make this night wonderful and special, so I''m still a bit torn. With the goal being to have multiple stops at her office, apartment, wine bar and finally dinner - I''m thinking that having an itenerary prepared for the driver will make the ''whisking around town'' romantic and fun for her. Like I said, the feedback is great and I''ll continue to ponder this part of the night.

Your statement regarding Pop''s is concerning. I definitely don''t want to go somewhere that will be packed and uncomfortable. I called and chatted with someone there and they predicted that if we show up between 6:00 and 7:00, there won''t be a wait. I am simply looking for a place to have one or two drinks. She''s not into the whole "what''s vogue" concept, she just likes champage - I''ll keep looking for alternatives.

A couple of quick questions for you regarding alternative to Pop''s. Like I said before, I''m really looking for a semi-posh place to have a drink or two and let her wind-down from the day in a romantic/comfortable environment. I would ideally like it to be quiet, quaint, scenic and somewhat romantic, but I realize people don''t always get what they want!

1) When you say ''Wine Bar in the Peninsula'', are you referring to ''The Bar'' or is there a bar inside the restaurant itself? The reason I ask is because I see the beautiful view of the water tower on the restaurants website, but the picture (only 1) of ''The Bar'' makes me inclined to think that it''s an non-windowed room - hopefully I''m wrong!
2) Regarding the Hyatt on Wacker - is the bar you''re referencing the ''Big Bar''? It looks like a great place, but their description sounds somewhat trendy and touristy with all their ''big drinks'' - am I looking at the right place?
3) Are you recommending Meritage as pre-dinner drink spot or as a restaurant? They actually have availability (no other place listed did!), so please let me know!

I really appreciate your information regarding these places. Obviously I would go to these places myself and find the best spot, but being in San Antonio doesn''t allow me to do that! Thanks in advance - I''m nervous about getting these details worked and ready to begin the celebration!

thanks, wally.
 

monarch64

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Wally, there is a very intimate little piano bar we went to in the Seneca hotel...it''s on street level, but it''s posh and should be semi-quiet around 6-7 even on V-Day. Here''s a link to the website if you want to call them for info :
http://www.senecahotel.com/hserv.htm

Then there''s the Drake--they have an afternoon tea room which serves cocktails in the evening...
http://dining.thedrakehotel.com/palmcourt/palmcourt_intro.html

For champage, with a very intimate setting:
http://www.narcisse.us/anteroom.html

and a less pretentious wine/champagne bar:
http://metromix.chicagotribune.com/localguide/neighborhoods/lincolnpark/27710,0,7887671.venue
 

flutterby

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Joined
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Sorry, this is going to be quick, will write more later. I wanted to second the seneca for a drink, its a cute place. But so is Nomi and the bar at the peninsula. If you have more questions about the peninsula, call their concierge they are super helpful.

I was mentioning meritage for dinner, I love it there! it is a bit of a trek from downtown though...its in wicker park. Now let me think if I could think of cute proposal bars near there..... hmmmmmmmmmmmmm. Do you know what neighborhood she lives in?

dont go to big bar! not romantic but amazing an HUGE drinks (think 42 ounces with icecream, yum)
 

wally

Rough_Rock
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Jan 30, 2006
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Wow, the Drake looks super-nice. Also, I like the idea of Webster''s - It''s quite close to Meritage and also close to her apt.

As far as the neighborhood that she lives in, I don''t know the name, but it''s on the north side near ''Boystown''? It''s near Belmont and Lakeshore, if that helps at all.

Do you guys feel that Meritage is a significantly better place to celebrate this sort of occasion than the Chicago Chop House?
 

flutterby

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Chop house and meritage are two different kind of places. Chop house is big and old school chicago steak house. Meritage is small, nice, neighborhood wine bar/restaurant. I love the chop house, but would rather go to meritage for v-day! I was thinking you could go to green dolphin for drinks before hand (or websters) they are all near eachother. Or you could go to websters then green dolphin for dinner. They are all in the same area, which is nice! I personally stay as far away from the big downtown restaurants on special days, and weekends, but that has to do with me and big crowds. My FI and I are just going to a byob restaurant for the day, its small and quiet and the owner/chef really cares about the food and the atmosphere. You should probably make reservations soon though. Let me know if you have more questions.
 

monarch64

Super_Ideal_Rock
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No Drake! They had a big problem with food poisoning or some "norovirus" over the weekend! Anyway, now they are cleaning up and sanitizing everything, which may make it the safest time to go, but I had to update you on this.

There is a bar/restaurant on the Gold Coast called the Bella Lounge-just found out about it today, one of my girlfriends just got hired as the special events coordinator. Their website is bellalounge.com, see what you think if you haven''t already made your decision.

I hope you have the proposal of your dreams! Best of luck, and have a great time no matter where you end up!
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We''ll be rootin'' for ya!!!
 

wally

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Jan 30, 2006
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First of all, thank you all VERY much for your help and insight! You guys were a great help and I appreciate the fact that you took the time to share all your valuable information with me!

Most importantly, she said YES!

The day worked out just about perfect - I managed to show up at her office around 4:00 PM and actually walk all the way to her desk and place the dozen roses on her desk before she even looked up to see who I was! She did a double-take and then hopped up and gave me a huge hug! She finished up a few things in her office and the introduced me to a couple co-workers which I had yet to meet before we headed down to the street. She asked if I''d prefer to take a cab or the train; but instead I opened up the door to the limo just in front of us and she was perfectly surprised! We went back to her place where she changed into a sexy pant-suit and we were back in the limo. The driver was supposed to take us to the Lily Ponds, but I''m not convinced that''s where he dropped us off! Regardless, we walked around the little pond just in front of the ''North Pond'' restaurant and, when the time was right, I popped the question. This caught her completely off-guard, but she was ecstatic! After I finished kneeling in the mud and got the ring on her finger, we sat down on a bench and I shared just how much she meant to me... (I think the ''Will you marry me'' popped out a little too quickly, so I wanted to share with her all the things that anxiety caused me to skip over while I was on my knee!).

It got a bit chilly, so we hopped back in the limo and headed to Pop''s. Unfortunatly, even though I had called to confirm, they didn''t open at 6:00 as their website touts. It worked out just fine as we went into Star Bar (same place, I guess) and had a bottle of champagne and a couple of appetizers. The ambiance was perfect as it was dark, not overly crowded and we had a great time being that grotesque over-infatuated couple in love!

We then headed (via taxi, the limo portion was over) to Meritage, which unfortunately was running behind. We got there right on time for our 8:45 seating, but they were about 30 minutes behind. We had a nice dinner, but it was the classic service/experience one would expect on v-day night. The service was hurried, the seating was in their outside tent and somewhat cramped and their outdoor heater allowed the patio to get too cold, then ran until the it was uncomfortably warm before shutting off. We also had people sitting next to it that were in a tiff, then proceeded to complain about the food and created a distraction (no fault of Meritage, except seating was very close) Honestly, it didn''t really matter as we were both on cloud 9 and happy as could be!

So, there''s the story! A picture of the ring is attached!

Thanks again for all your help!

-wally

wally2ring.jpg
 

wally

Rough_Rock
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Just a quick note, the ring pic is NOT the final version of the ring. I custom designed the ring and this is a picture taken before the final finishing touches were added. Once the ring was complete, all the lines were perfect smooth and polished, not jagged like this pic!
 

Cailet

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awwww - Congrats Wally! Sounds like it was a great night!!
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The ring is beautiful - now get some of those famous hand shots up
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monarch64

Super_Ideal_Rock
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Holy Moly, I don''t know how I missed this!!!!!!!!
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CONGRATULATIONS Wally!!!!
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I''m so glad to hear your proposal turned out so well. And the ring is beautiful (so far!). So when are you moving to Chicago so we can all have our very own PS get together?! LOL!
 
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