I've got a really good friend traveling to Chicago in September with his girlfriend. I can tell him a number of things to do and places to d go but this one is a bit trickier. Any input on a romantic and memorable Chicago setting to propose?

They're staying at the W Hotel near Navy Pier.

I’d probably take one of those lake tour boats near sunset time and pop the question against the backdrop of the Chicago skyline and sunset. They all launch from Navy Pier.

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I always preferred the River tour but for this, I agree. To see the entire skyline would be an incredible backdrop for something like this.

What type of person is she?

I like places with Champagne or someplace like the lily pool.

dolphin will probably tell you Wrigley Field. Hopefully no carjackings or shootings nearby. Don't do this...

viewtopic.php?f=128&t=110054&p=2872181&hilit=proposal+spiegel#p2872181

Is the bar and restaurant atop John Hancock still open and solid?

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L&L Tavern

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At a minor league game so everyone can see it on the jumbotron when she freaks out and says no.

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"I honestly don't see a good bet on the board here."

Pop the question while flicking her bean in front of the bean.

Don't do it!

I thought for sure this would be a Whistler thread

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This guy gets it

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Fare you well, fare you well
I love you more than words can tell
Listen to the river sing sweet songs
To rock my soul

god damnit

make a secret bank account and keep stripper money in it

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Thank you Dennis, Spaulding, and RR. The rest of you should go on tour.

Looks like the Signature Room is still open. I think over at the Sears Tower you have to be a member to get a reservation at their restaurant? Maybe I have that wrong. Signature at Hancock has been around much longer, correct?

There's a signature at the sears tower?

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http://soundcloud.com/darkside124 HOF 2013, MM Champion 2014

That was a poorly written sentence. Signature is open at Hancock. No Signature at Sears but they do have a nice restaurant on the top floor. I think you’ve got to be a member to eat there?

If you want to go that route London House is suppose to be good. They have a package, I can't imagine the cost. Otherwise the restaurants there might be okay too.

Tell him to not attention whore. It's a private moment between two people and filled with enough emotion on its own that no staging is necessary.

Find a quiet location. The island at Northwestern U is right on the lake with a great backdrop of the city or the Japanese Garden at the Museum of Science and Industry.

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Spaulding and GD

Correct. Don't do a "Jason Goff" is what you're saying. All kids should learn that lesson from him.

Makes me wonder if dolphin thinks he does romantic stuff but doesn't really, could not want the hassle and price could be a factor.

My husband and I went golfing and then to feed ducks at a nearby pond. I love ducks and could watch them for hours. It fit us in sort of, I don't think it's a great story by any means though, if pushed I'd say it lacked something in a way. I think a food thing would have been more fitting like grabbing a cake or cupcakes from a bakery. I am glad it wasn't really public though. I love pictures of people that get engaged somewhere like Paris or Venice but no way we could have done something like that. It doesn't have to be expensive I suppose but there should be something meaningful about it. I could see having a great day out and then having something back at the hotel arranged for the room or breakfast in bed in the morning.

I would hate any sort of hike or boat, you have to know your girl. Some might like that type of thing.

Cooper Hawk, and as an engagement gift buy the future bride a wine of the month club subscription after she finishes her Ellie's Chicken Picatta and a S'MORE buddino.

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You do not talk to me like that! I work too hard to deal with this stuff! I work too hard! I'm an important member of the CSFMB! I drive a Dodge Stratus!

That was my grandmother's favorite. They've come to Scottsdale recently and another restaurant is on its way in Chandler.

do it here

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Private booth at the Pink Monkey.

What a fantastic idea.

I proposed at the Hancock Observatory in the open air area as a storm was rolling in.

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RAIN OR SNOW STORM?

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Rain. I wanted to make absolutely sure I'd never forget our dates so I asked her date me and marry me on 9/11. This was, of course, before "the 9/11".

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I'm disappointed the US won gold in basketball so I didn't get to do my "Best place to question the Pop in Chicago?" parody thread.

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You do not talk to me like that! I work too hard to deal with this stuff! I work too hard! I'm an important member of the CSFMB! I drive a Dodge Stratus!