Your thoughts on my ideas for Chicago? Any suggestions or tips?

[SkiRush]

Hello all, I''m looking to propose to my girlfriend after Christmas. We will be in Chicago and I''m thinking of the ideas below. I think the first one will be obvious with no element of surprise, but can still be nice.

1) There is a company that arranges for horse drawn carriage rides. They offer an engagement package where the driver arranges to meet you at a location and time, and acts casual. He stops at a pre-determined picturesque location to "take pictures". The driver asks if we would like him to snap photos of us. We would get out and then propose. After we get in, the driver hands her a dozen roses that were tucked away.

On one hand I like the idea of a horse drawn carriage ride. But, I think it might be a dead give away, because I''m pretty frugal and typically don''t spend money on such things. Also, does the fact that they offer an engagement package sound somewhat cliche?


2) I took my GF to Chicago on our first valentines day together. We had a great time skating at millenium park. So, I was thinking we would go skating again to re-live that moment. I would guide her to the center of the rink and then get down on one knee. I would be a little nervous in front of all those people, but oh well. The only potential problem with this plan is that the skating rink is much much busier right after Christmas than it was when we went in Feb. I''ve seen the line with over a 2 hour wait.

What do you all think? Are they both cliche? Any other tips, suggestions, good spots?


Thanks,
SR

 

[Regular Guy]

Either of these might be lovely.

I just celebrated a big # birthday with my wife, and maybe for that reason, this approach is in my mind. (We had a nice Italian dinner in Baltimore.) I hail from Chicago, found the Italian Village restaurant very romantic, and I see they''re seemingly still in business.

Just another idea you might want to check out.

 

[AprilBaby]

The Signature Room at the top of the Hancock Center at night is VERY romantic as is Gejas Restaurant on Armitage Ave.Just worried about how cold it might be in Feb outside. http://www.gejascafe.com/

 

[cspear]

If you are trying to decide between the two ideas I think your #2 seems more personal. Although both sound like good ideas I think you are right, that having an "engagement package" sounds a little cliche.

Is there a time of day when the crowds at the skating rink are less hectic. Could you arrange a midweek proposal or a late evening before the close? Or, just an idea, maybe you could talk to the manager of the rink and see if you could arrange to have the skating rink opened up just for the two of you late one night after a dinner. You two could skate and you could propose.

Just my 2 cents.

 

[KatM]

i like idea #2 better also. the ice rinks are really beautiful (especially over at millenium park where there are a ton of photo ops) and the carriage operators here are always getting tickets for the poor conditions of their horses.

 

[havernell]

I also think #2 (the skating rink) sounds better than #1 (the carriage ride). The second is just more personal to me since it''s something you guys did together in the past. The first is just kind of generic (which is why they have the package, as you pointed out). So, as a female, the skating rink would be my preference.

I second someone else''s suggestion about trying to find a time when the rink would be less croweded (i.e. in the morning, mid-week, etc). OR, if it''s going to be crowded at all times that week after Christmas, are there any lakes or ponds that freeze over just outside of Chicago in the suburbs that you can skate on? If so (and if you have your own skates) perhaps you can go there to propose. It would also be more private, which could be nice if you get the sense that your girlfriend wouldn''t be into a big public proposal.

Good luck figuring everything out!