Chicago People I Need Your Help.

twistedredbird

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Apr 26, 2008
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You seem like a good guy so I am sure she love the ring because it is from you. Girls that get hung up on ring size are not in it for the right reason.
 
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CyBer

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You seem like a good guy so I am sure she love the ring because it is from you. Girls that get hung up on ring size are not in it for the right reason.

Truer words have never been spoken and I think there is a study between diamond size of engagement rings and how long the relationship lasts.
 

HFCS

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Aug 13, 2010
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You seem like a good guy so I am sure she love the ring because it is from you. Girls that get hung up on ring size are not in it for the right reason.

A girl who tells you she'd rather have $800 more of one dinner instead of $800 more ring is lying. That's all I was saying, and I'm quite certain it's true 99% of the time ;-)
 
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CyBer

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Honestly... she came up to me at the dining center saying she saw me playing Ultimate the day before. We chatted it up and then it went from there lol

Nice, I met my girlfriend trying to "sell her tickets to the circus that was in town" I don't remember any of this because I was plastered drunk my freshman year. Apparently she saw something in me, what exactly I have no clue about.....
 

twistedredbird

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I was either going to do it at dinner or maybe by the bean or something.

I wouldn't do it at dinner but maybe somewhere unexpected. In the cab. At a crosswalk. In front of the Bean sounds cool. The trip to Chicago. Before dinner in the hotel. You will be nervous she will know something is up. Id get it out of the way early to set the stage for a romantic evening where she will be all googly eyed. You will then enjoy it more too.
 
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CyBer

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I wouldn't do it at dinner but maybe somewhere unexpected. In the cab. At a crosswalk. In front of the Bean sounds cool. The trip to Chicago. Before dinner in the hotel. You will be nervous she will know something is up. Id get it out of the way early to set the stage for a romantic evening where she will be all googly eyed. You will then enjoy it more too.

Looks like this is the general consensus, I'll find somewhere cool.
 

Cycsk

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I'm proposing to my girlfriend in Chicago in the second weekend of August and I'm in need of a good restaurant to go out to dinner (I might propose then or later at a park haven't decided, but probably at dinner). So I'm looking for something romantic where she can dress up. Afterwards I was thinking about going to celebrate at nice bar or something. I'm not looking for $100 dollar plates or anything, but something pretty nice and maybe low lit (cuz I'm ugly :jimlad:).



Thanks for the help in advance.



Lived in Chicago for 24 years. Easy choice: The Signature Room.

This fantastic restaurant is at the top of the John Hancock Building. It has a great bar. Both the bar and the restaurant have views all four directions (lake, downtown, north lakefront, near north side). It has the best views in the city by far. Tell them in advance what you are doing and they will make sure you get a great table. I used to take people there for lunch because it is actually pretty reasonable priced for lunch. It will be expensive for dinner, but worth it. And it is famous for being a place for classy proposals.

Cyber, you owe me daily reps for a month for advice this good!
 
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CyBer

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Lived in Chicago for 24 years. Easy choice: The Signature Room.

This fantastic restaurant is at the top of the John Hancock Building. It has a great bar. Both the bar and the restaurant have views all four directions (lake, downtown, north lakefront, near north side). It has the best views in the city by far. Tell them in advance what you are doing and they will make sure you get a great table. I used to take people there for lunch because it is actually pretty reasonable priced for lunch. It will be expensive for dinner, but worth it. And it is famous for being a place for classy proposals.

Cyber, you owe me daily reps for a month for advice this good!

Yeah I was going to go there for drinks after dinner.
 

Cycsk

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Westin Chicago Hotels: The Westin Michigan Avenue Chicago - Hotel Rooms at westin

tHE gRILL ON The alley..... on ground floor of The Westin--separate entrance

Right on Michigan and the side street that is next to (north) of the John Hancock Building.

If it's a clear night---take her up to the Hancock observation deck after dinner. awesome views



Skip the observatory and go to the bar in the John Hancock Building. It is called The 96th Lounge (it is just above The Signature Room on the 95th). Spend your money on drinks. Don't wait in the observatory line. And have the kind of atmosphere you want.

At any of these places, if you let them know what you are doing, they usually have ways to make it really special. Just tip well, maybe even in advance.
 

Cycsk

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Yeah I was going to go there for drinks after dinner.



Now that I see that you are staying at The Talbot, I have a spot for another meal. Go a block or so west of The Hancock Building to Ditka's (yes, that Ditka). It has a football theme, but it is a really classy place. Think the Downtown Athletic Club in New York where they award the Heisman.

There are also some really classy places nearby. Of course, the Westin, but also the Drake (as long as you don't have Drake U issues).

I would recommend that you cruise Rush Street (parallel to Michigan Ave, but a block west). Lots of great restaurants and bars. Even a Lambergini dealer! And the downtown campus of Loyola University (right next to the Water Tower).
 
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CyBer

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Now that I see that you are staying at The Talbot, I have a spot for another meal. Go a block or so west of The Hancock Building to Ditka's (yes, that Ditka). It has a football theme, but it is a really classy place. Think the Downtown Athletic Club in New York where they award the Heisman.

There are also some really classy places nearby. Of course, the Westin, but also the Drake (as long as you don't have Drake U issues).

I would recommend that you cruise Rush Street (parallel to Michigan Ave, but a block west). Lots of great restaurants and bars. Even a Lambergini dealer! And the downtown campus of Loyola University (right next to the Water Tower).

I'm thinking I'm going to propose in the Lincoln Park area, maybe hit up the Field Museum in the day and then when the sun starts setting ask her, then go to dinner and then out for drinks.
 

isuno1fan

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If you take her to a place unlike you normally go, she may be expecting it. I'm a fan of keeping it simple and I think that also makes the moment more surprising.

To each their own, but I proposed in my living room out of the clear blue and shocked the heck out of my gal.
 

Cycsk

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I'm thinking I'm going to propose in the Lincoln Park area, maybe hit up the Field Museum in the day and then when the sun starts setting ask her, then go to dinner and then out for drinks.



My dad proposed to my mom in Lincoln Park (in 1953!). And I broke up with my college girlfriend there (in 1986). Those were some of the best decisions my dad and I ever made!

There are lots of great places in the park, but you might want to scout it out first.

You might want to take her to a concert at the Ravinia Festival up in Highland Park (north suburbs). Most of the people lay on blankets and watch the stars as they listen to the concert. Lots of folks bring dinners and wine. You aren't alone, but you will probably get a nice round of applause when you propose. Lots of nice, rich people in good moods at Ravinia.

However, I still think doing it over drinks at The 96th Lounge as you look north or south over the lakefront is the best idea. Get the waiter to help you make it special. Have him put the ring in her drink. Or set it down on the table as he brings your drinks. If he knows what you are doing, he will get you exactly the table you want.
 
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CyBer

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If you take her to a place unlike you normally go, she may be expecting it. I'm a fan of keeping it simple and I think that also makes the moment more surprising.

To each their own, but I proposed in my living room out of the clear blue and shocked the heck out of my gal.

I've been telling her that I want to take her to Chicago for about 3 years now, she might be expecting it, but I think it would be a very good place for a proposal.
 
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CyBer

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My dad proposed to my mom in Lincoln Park (in 1953!). And I broke up with my college girlfriend there (in 1986). Those were some of the best decisions my dad and I ever made!

There are lots of great places in the park, but you might want to scout it out first.

You might want to take her to a concert at the Ravinia Festival up in Highland Park (north suburbs). Most of the people lay on blankets and watch the stars as they listen to the concert. Lots of folks bring dinners and wine. You aren't alone, but you will probably get a nice round of applause when you propose. Lots of nice, rich people in good moods at Ravinia.

However, I still think doing it over drinks at The 96th Lounge as you look north or south over the lakefront is the best idea. Get the waiter to help you make it special. Have him put the ring in her drink. Or set it down on the table as he brings your drinks. If he knows what you are doing, he will get you exactly the table you want.

Meant Millennium park haha.
 

Cycsk

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Meant Millennium park haha.



Oh well, I had a good time on that stroll down Lincoln Park lane!

Millennium Park can be crazy during the summer, especially if there is a festival going on. For instance, would it help or hurt your plans if Loolapalooza were going on?

If she likes art, you might want to take her to The Art Institute (on Michigan Avenue and actually in the Millennium Park complex). Give her the ring while you are looking at some multi-million dollar Monet paintings! The Art Institute is one of my favorite places to go.
 

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